I grew up in Chicago, so I’ve always been really nostalgic about Christmastime there. When Matt and I found a deal through American Express that refunded one night of any three-night stay there, it was hard to say no. Especially when one of the cheapest hotels ended up being the very fancy Renaissance Blackstone on the Magnificent Mile, and plane tickets were cheap.

We decided to fly Sun Country rather than Delta, because even though tickets were the same price, Sun Country goes to Midway. That’s way more convenient when you’re taking the train. We flew out of Minneapolis around 5, and landed in Chicago by 6:30. Since we just had carry-ons, it was a quick trip from the plane to the Metra.

We rode into downtown and got off at the first stop down in the south Loop, an area I wasn’t very familiar with. In the past it had not been the greatest neighborhood, but it’s definitely becoming gentrified now, with a lot of the warehouse-style condos that tend to spring up in those areas. We walked the six blocks or so to the hotel (walking along Michigan Avenue in the cold isn’t smart, by the way… go inland from the lake!) and checked in. As expected, our room was really fancy… the Westin is usually my standard for nice hotels, and this was a step up.

It was after 8pm, but since we’d had sandwiches on the plane we weren’t dying for dinner yet. We decided to get cocktails at the hotel bar, which is downstairs from the resident tapas place, Mercat a la Planxa (we were excited that it’s run by an Iron Chef, too). The place was tiny and well-appointed, the ideal kind of hotel bar. They had a great cocktail menu, too.

We had decided on getting our deep dish needs out of the way early at the nearby Lou Malnati’s, partly because we didn’t want to take the train anywhere since we were planning to buy passes the next day, and it was getting late. The bartender confirmed the directions for us, and we headed out in the cold. On the way there, we took note of two bars we might want to visit later; one was a big, packed sports bar, and one appeared to be a liquor store that you could also drink in. (That one was the instant favorite, of course.)

I’ve only been to Giordano’s before, so this was an exciting change! Also exciting: they had personal-size pizzas (you always end up with tons of leftovers at Giordano’s), and Goose Island Matilda. Perfect.

After dinner, we stuck with the ‘things to always do in Chicago’ theme and headed up to Miller’s Pub. The sign out front advertised that they had Tom and Jerry’s, which was fantastic. The bar was crowded, but we managed to find a standing spot at the far end and ordered our Tom and Jerrys. They were pretty sweet, but the large quantity of brandy (and the warmth, since it was really cold outside) made up for it.

We stuck around for another round, at which point I switched to a gin martini to avoid the sweetness issue. I was trying to eavesdrop on the people next to us, which appeared to be a couple of coworkers. The guy was older and the woman was pretty young, and he was drunkenly trying to hit on her in a very subtle (but not really) way. It was very entertaining.

Round about midnight, we decided to head back toward the south Loop and stop in at one of the bars we’d seen earlier. We decided on George’s, the liquor store that apparently had a bar inside. That’s exactly what it ended up being, too… a total dive with a bar and a few small tables (and awesome jukebox), with a wall of liquor you could buy for exorbitant rates along the back wall. It was the BEST. The bartender was old and crusty, there were loud Wisconsinites manning the jukebox, and drinks were incredibly cheap.

Though the bar was open til 4am (!!), we were at least a little bit smart, and decided to leave at 2. Thankfully it was only a block from there to the hotel.

—–

The next morning, we got up and went downstairs to Starbucks for coffee before walking to the el. We purchased three-day passes, then hopped on and rode up to the north side of the Loop. Our destination was Daley Plaza, for the Christkindlmarket. Apparently it’s been going on forever, but I had no idea! I was incredibly excited to see it.

The pigeons there were smarter than the average bird, too:

The place was insanely crowded, of course. It was convenient that there seemed to be multiples of most of the food and drink booths, so that you didn’t have to push your way across the entire place to get something to eat. We saw people carrying little souvenir mugs all over the place, so I wanted to check that out first. It ended up being gluhwein, so Matt got one of those and I got a beer instead.

We did some wandering around the shops, and noted one of the gigantic shops full of traditional glass ornaments that I wanted to visit once we weren’t carrying drinks. We decided to stop at get breakfast first, too. I got potato pancakes, and Matt got currywurst. Some people joined us at our table, and it seemed like the whole city was excited to be there, even though we were freezing our asses off.

After the food, we went to the ornament shop. There was a line to get in, so I shivered there for 10 or 15 minutes before we actually got inside. From there everyone had to grab a basket and circle slowly around the store, following a pre-established path. You had one shot to get the ornaments you wanted, or you’d have to wait in line again. It was probably the most German thing ever.

I picked out a few things, and appreciated the fact that they wrapped and boxed them up really well. From there, we went to get another beer and go hang out in one of the heated tents to warm up. The tents were also packed, of course, but we didn’t care. We found a spot near the heater and I regained feeling in my feet.

Before heading out, we stopped to get a couple pretzels, and ate them outside in a sheltered spot. I would probably have stayed there all day if it wasn’t so cold out. (It was still 20 degrees warmer than home, though!)

We walked over to State Street to go see Macy’s, the former Marshall Field’s. I have vague memories of that store and Carson Pirie Scott being all decorated at Christmas, and I wasn’t wrong about that. We did some shopping, then took the escalator up to see the giant tree in the restaurant.

Then we decided to head over to XOCO for a late lunch. On the way, though, I had to stop into Walgreens to pick up some things, like super-strong hand lotion (stupid cold), hairspray, and Christmas cards for my nieces in Florida, since we wanted to send them some cash instead of gifts.

Our timing regarding late lunch was planned as follows: wait in line for a torta. Eat a torta. By the time we’re done with tortas, Three Dots and a Dash will just be opening. Since the place is very new and very popular and it was cold outside, we wanted to make sure we got in right away. Plus, you know, afternoon tiki drinks.

We decided to walk, since it was only six blocks or so. We crossed the river, stopped into Citibank to break a hundred (so my nieces could have their Christmas gifts), and then headed over to Xoco. To our surprise, there wasn’t even a very long line! I got a beer and Matt ordered one of their bottled margaritas, and we went to wait at our assigned counter spot. The food took a while, but that was fine because it was a good opportunity to warm up.

My woodland mushroom torta was fantastic, too. There need to be more vegetarian tortas in the world.

Since our lunch went faster than expected, it was only 4pm and Three Dots wasn’t open. So we did what all good Midwesterners do in the winter: we went to another bar to wait for it to open. The Boss Bar came recommended by Foursquare as a classic dive, and it was only a block away, so we headed that direction. Holy crap, the place was insane at 4pm. It wasn’t just people at post-work happy hour, either… it seemed that many of them had probably been there all day. Also, one of the walls was being held up by 2x4s, and the kitchen was just a little kiosk with a deep-fryer near the entrance. AWESOME.

We killed time with a drink there, and then promptly at 4:30pm headed over to Three Dots. It’s in the alley behind Xoco, complete with bouncers in black, velvet ropes, and heaters (thank god). But seriously, it was 4:30pm, not 11. Anyway.

We went up to the doorman, and he told us that they were closed for a private party. (Sad!) But the private party only went til 5:30. (Hooray!) Rather than wait outside, we walked to yet another bar. I had seen a place called Havana as we walked past before, so we decided to go there. I didn’t exactly know where it was, though, so we circled the entire block before we ended up there, directly next to the Boss Bar we’d just come from. At least we got some exercise.

The nice thing about places named after Cuba, or any really Caribbean island, is that you have a good idea what to expect there, and you’re rarely disappointed. Havana was a small, pretty restaurant with a very nice bar and better rum selection. We had mojitos, and the bartender made them perfectly, not too sweet.

Shortly after 5:30, we walked back over to Three Dots. The private party was taking their sweet time exiting the place, so they said it would be after 6 by the time they actually opened. We didn’t want to ruin our streak of waiting in bars, so we went to Mother Hubbard’s Sports Bar (it was not that awesome) to warm up and use the bathroom. Matt was excited that they still tacked newspapers up over the urinals to read. I didn’t even know that happened!

We made our way back again around 6, and this time found an actual line in the alley. It was only ten people or so, but still. A line! At 6pm! I’ve never seen that before. We stood there for a while, shivering and wondering if we’d ever get in, because the line wasn’t moving and there were still work-party people milling around and going in and out of the bar. FINALLY, the bouncer came over and started letting people in. We were taken downstairs to a table, and immediately knew it was absolutely worth the wait.

The place is decorated in usual tiki/nautical style, and the drinks are half classic and half inspirations on everyone’s favorite giant picture menu. (If I own a tiki bar someday, we’re going to have the largest illustrated menu on earth). The thing I loved most was that the drinks are less sweet than the originals, and they pay a lot of attention to presentation.

We had three cocktails apiece, plus a couple very delicious appetizers, and then it was time to go lest we just decide to live there forever (I would). Plus the place was getting crowded to the point where people were bumping into our table and yelling over each other. We requested a souvenir glass, paid our check, and headed back out into the cold.

We decided to walk again and see what was on the way, since we didn’t have any great ideas for dinner yet, and we’d just had appetizers. Conveniently, we ended up passing right by the Palmer House, so we decided to go visit another classic. We grabbed seats from someone who was vacating them at the lobby bar and ordered one of their house Manhattans. Then I took out the Christmas cards for my nieces and filled them out on the bar, so we could mail them right away. It’s my goal for us to be known as the super-classy aunt and uncle.

When we were done there, we decided to just go back to the hotel and check out Mercat a la Planxa. We’d looked at their menu in the room enough to know that they did actually have vegetarian stuff, and it seemed like an easy choice. We started walking back that way, and within a couple blocks of the hotel, it started sleeting. Just like at home in Minnesota! We rushed back, dropped our stuff in the room, and went down to the restaurant. It was 10:30 and they closed at 11, but they told us it was no problem. Thank god, because we were dying of hunger at that point.

Not only did they have vegetarian stuff, they said they could do a tasting menu for both of us! And holy crap, it was fantastic.

The only downside was that the food just KEPT COMING. We were getting full, to the point where we were hoping it was over, and then more would arrive. I should’ve taken it home in my carry-on or something.

Back in our room, we had truffles from the front desk, because we’d mentioned being fancy on Twitter. Cute!

At that point it was after midnight and we were hella full of delicious tapas, so it was time for bed.

—–

I woke up sometime early the next morning and noted blearily through my contact-less eyes that it was snowing. And not just a little bit, but a full-on blizzard. Lake Michigan seemed angry. After a couple more hours of sleep it was starting to die down, but not enough to make wandering around outside all day that feasible. I was glad we’d gone to the Christkindlmarket the previous day.

Conveniently, we’d talked about visiting the Art Institute, since neither of us had been there in a very long time. And conveniently, it was only a few blocks away!

Our time was limited there, but we managed to cover a lot of ground. We saw most of my favorite things, which include the impressionists and anything modern.

The views from the building, which has expanded a lot since my last visit, confirmed that we didn’t really want to be outside that much:

We visited the Chagall windows, which for unknown reasons was my absolute favorite thing as a kid, and then went downstairs to have lunch in their really excellent cafe. I had a delicious falafel burger.

We stopped to take a quick spin through the miniature rooms (also a longstanding favorite), and then it was time to head out, because for once we had actual plans! We hopped on the train to Logan Square, home of Matt’s longtime internet pal, Kyle from Midmajority. More importantly, Kyle is the inventory of our constant travel companion, Bally.

We took the longest possible route around Logan Square (whose intersections had all become treacherous pools of indeterminate-depth slush) and found Billy Sunday, the new cocktail bar on the block. Their menu was fantastically interesting, and rather than trying to explain it, here’s the link. Kyle showed up a few minutes after we arrived.

We hung out there for a couple drinks, and then headed out to get some dinner. Kyle led us to Parson’s Chicken and Fish, which, despite the name, also had vegetarian stuff on the menu, not to mention things like a Negroni slushy. I had the vegetable club, made with pickled beets. They had good beer, too, and Bang Bang Pie. (No, I didn’t know what that was beforehand.)

From there, we walked over to Scofflaw, another awesome cocktail place. It was standing-room crowded, but we were conveniently standing next to some girls who were leaving and gave us their armchairs around a little table. There was a fireplace in the room, too, so it was quite comfortable.

After a cocktail there, we grabbed a cab to Wrigleyville. We ended up talking about how Indiana was a huge wasteland, and our driver piped right up with stories about how much he hated Indiana because people were racist and did horrible things to his middle-eastern friends. Holy crap, Indiana, what’s your deal??

We were a little early for the show, so we went to Gingerman Tavern next door for a drink. It was much like Triple Rock or Grumpy’s, so we were right at home. We had beers there, and then went next door to Metro for the Breeders show.

I was expecting Metro to be a lot bigger, since they get the shows that First Ave generally does, but it was definitely smaller. Which was nice, because even though we ended up at the back, we had a good view.

Confusingly, both Matt and Kyle encountered really aggro dudes there. That’s definitely not something that ever happens at First Ave. Minnesotans like to keep their rage inside.

After the show, we were standing in the coat check line talking about the cab driver who hated Indiana, and ended up talking to a girl from Fort Wayne who could not understand the concept of flying from Minneapolis to Chicago. (It’s a long drive, and a generally very cheap flight!)

We hopped in another cab and rode back up to Logan Square to the Empty Bottle for the Windy City Soul Club 5th anniversary event. The place was packed with people actually dancing! And they had a really good bourbon drink on special! It was amazing. We hung out with Kyle’s friends there for a while, Kyle introduced us to the wonders of Malört (it’s godawful, as you’d expect of herbal Swedish liquor), and then we headed off to yet another bar in the neighborhood, the Blind Robin.

I took their photo with Bally, and it turned out GREAT in the darkness. Haha.

Finally, it was time to head back to the hotel. We got another cab since we were about a mile from the train, and apparently cabs in Chicago are way cheaper than Minneapolis!

—-

Sunday morning, we hung out in the room until close to check-out time, and then left our bags with the front desk. We picked up coffee at Dunkin Donuts, then rode the train up to Wicker Park. Rodan was a couple blocks from the stop, and we were apparently the only ones there for brunch at almost 1pm. Strange.

They had bottomless mimosas for brunch, which sounded like a great idea for people who had a few hours to kill before their flight. (It was colder outside than the previous days, too.) The food was great, too. We finished and then sat there for a long time while they refilled our drinks; it seemed easier to get mimosa refills than it was the check, but that was fine with us.

Finally we headed out, and rode the train back to River North. Our destination was Eataly, the Italian market/deli that had recently opened in Chicago and had lines around the block at the opening. Walking in, I immediately realized why. It was HUGE, and wasn’t just a deli. They had several different spots in the building that were mini-restaurants, with things like pizza, fresh bread, a wine bar, charcuterie, pasta, truffles, a brewery, and even a mozzarella bar. HOLY CRAP. I was sad we had just eaten!

We wandered around and looked at the merchandise for a while, then went to the brewery. They brewed their own beer there, as well as doing contract brewing for Dogfish Head. I got an ancient ale (a style I’d never tried before), and we went to wander some more. I wanted to get to the mozzarella bar even though I was full, but it was full every time we walked past.

Matt picked out some packaged meat to bring home, and we picked out black rice for risotto. We would’ve bought some black truffle, but they weren’t getting them in until the next week. We picked up some fancy chocolates to take home, and a few other things from downstairs before going to check out.

We still had some time to kill before needing to be back at the hotel, so we did what anyone else would do: went back to Miller’s Pub for a victory lap. The place was crowded again, this time with Chicago Bears fans who had apparently come from somewhere else (the Bears were out of town). They were in post-tailgating condition, and hilarious to listen to with their super-strong Chicago accents. It reminded me of when my dad used to put on his cop voice years ago, and he sounded like Dan Aykroyd in the Blues Brothers. We had one last shot of Malört in Kyle’s honor, and then headed back to the hotel to pick up our bags.

We rolled them to the train station just as it was getting dark outside. We rode to Midway and discovered our flight was delayed (it was late leaving Montego Bay: SHOCKER), so we got a table at Harry Caray’s to get dinner and beers. Once we were done, our flight was further delayed, so we hung out at the pub waiting for it to arrive. It finally arrived, and we got home without further incident.

Saturday morning, we headed to the airport shortly after 8. We parked at Humphrey (I can’t deal with this “Terminal 2” crap) and took the train to the main terminal. Since Delta had upgraded us to first class, we got to go through the priority security lane and everything. We stopped at Caribou for coffee and breakfast sandwiches, and headed to the gate.

While I was in the bathroom, the agent announced that the flight was overbooked, just like every Delta flight since the beginning of time. They were offering $400 to take a bump to the next flight an hour and a half later. We thought about it for a minute, and decided we should volunteer. I wasn’t sure they’d want to trade first class tickets, but I went to wait in line anyway.

I waited forever, and then the agent finally made the announcement again. I waved our boarding passes, and she called me up. She said first class was fine, and they’d give us $300 and meal vouchers. We weren’t even sure whether it was $300 total or apiece, or why the first announcement was for $400, but I didn’t really care. Even $300 for a 90 minute delay was totally fine with me.

She told me to hang out til the end of boarding, because there was a chance we could still get on the plane. I was hoping not, because I wanted that deal. We had to wait around for at least 20 minutes for them to finish everything, but the plane was indeed full. A different gate agent took us to get the vouchers, and she asked, “Did she offer $400?” I said yes, because I’m not stupid. We walked away with $800 in flight vouchers and first class seats on the next flight. We didn’t really complain about not getting the $6 meal vouchers.

So it was already the best trip ever, and we still hadn’t left the airport. We walked over to our new gate area, and got a celebratory beer at Ike’s. We had an excellent and quick flight to Chicago, and took advantage of our first class benefits along the way.

At O’Hare, we boarded the blue line and rode into town. We hopped off at the Chicago stop, planning to have lunch at the Silver Palm. It was right across the street from the station, but it was closed for a private event. We asked a guy there if he had lunch recommendations, and ended up at the Windy City Cafe instead. There we had a good brunch and a really awesome server.

We got back on the train and rode to the hotel. We arrived at the Palmer House Hilton right as check-in was beginning, and the place was mobbed. From the looks of it, everyone there but us was arriving for weddings. I waited in line while Matt went to the (really pretty) lobby bar for cocktails. (Standing in line with a Manhattan makes everything more pleasant.) We got a corner room on the 19th floor with a good view, and I was surprised to see how many buildings in the Loop have green roofs. That’s pretty awesome.

We headed out to go be tourists for a while. Our first top was Millennium Park, to see the Cloud Gate (aka the Bean).

On the way there, we bet on how many wedding parties we’d see having pictures taken in the park. Matt said 100, and I went the slightly more reasonable route with 7. I worried that he might be correct, since we saw 2 of them before even getting to the Bean.

We walked around for a while, then decided to head over to the rooftop patio at Tavern at the Park for a drink. It was hot out, and the patio was mostly in the shade. They had Goose Island Matilda on tap, too!!

From there, we walked to the red line and rode up to the John Hancock building. I hadn’t been up to the observation deck for a while, and it was a good day for it. Plus it was surprisingly uncrowded. (It seemed that everyone in the building was waiting in line to get into Cheesecake Factory. I’ll never understand that.)

On the west side of the building, I discovered a gigantic spider just waiting to descend and wrap the entire city a huge web. Look at him!

We headed back to the hotel to shower (because it was still ridiculously hot) and change into our fancy evening clothes. We did have cocktails in the shower, since nobody wants to be overly classy on vacation.

We took the red line back up to the same part of town we’d been in, and walked over to Frontera, where we had reservations at 9:15. We started with the guacamole, which was way better than anything we’ve made (even though we use Rick Bayless’ recipe), and fresh corn tamales. Matt ordered pork tinga tacos and venomous beans, and I got the mushroom tacos al carbon and a side of plantains with cheese. The tacos were so ridiculously good I couldn’t believe it, nor could I believe how full I was after finishing one of them. I did my best with another taco, but barely survived. Our server thought I didn’t like them, but I was just sad I couldn’t have more. Everything there was so good.

After dinner, we walked six blocks north to a cocktail bar that ended up being closed when we arrived, possibly permanently. We decided to go to the train and head back to the neighborhood near our hotel instead; I really wanted to go to Miller’s Pub, because it’s so awesomely oldschool. We sat at the bar and had Manhattans, and admired the hobo artwork on the wall. When it was time to go, we just had to walk next door to the Palmer House. Convenient!

The next morning, we got up at 9 because we had a car-date. We had made arrangements to borrow someone’s car on RelayRides.com, which is infinitely more convenient and cheaper than renting from an agency. Our reservation was actually for noon, but the owner contacted us to see if we could go earlier instead. That was fine, because he said he’d drop the car at our hotel instead of us having to walk down to his apartment. He got there and showed Matt how to use the GPS and such, then took his bike off the back and rode off to do his thing while we drove his car to the suburbs.

One of the goals on my 101 Things list was to go take photos of every place I’ve lived. I’d gotten to all of them (i.e. the ones in Minneapolis and Milwaukee) except the Chicago locales; even though I’d visited them before, I wanted to go back and take new pictures. So we headed to Addison first, where it was pouring like crazy when we arrived. We saw my first home there, then the school where I attended kindergarten, and then we stopped at Dunkin Donuts for some coffee.

From there we headed to Wheaton for the other three: two townhomes my parents rented in between houses, and the house they built there, which still looks very much the same, with way bigger trees. We also drove around downtown Wheaton, which is still as cute as it always was.

Then we went to take care of another important piece of business in the suburbs: Portillo’s. My vegetable sandwich wasn’t the greatest, but the fries and nostalgia more than made up for it. 

We headed back to downtown, experiencing the best of Chicago traffic along the way. We texted the car’s owner to let him know we were back, and he came to pick it up from us within a few minutes. RelayRides? Good system.

It was still sprinkling a little outside, so we got our umbrellas and headed over to Grant Park. (I don’t think I’ve ever visited Buckingham Fountain in nice weather, come to think of it.) We walked south toward the Field Museum, which was a little over a mile away. There was hardly anyone there, probably because it was getting late in the day. We had to hurry to see things.

Our tickets included passes to one of their special exhibitions, so we went to go learn about Ghengis Khan. That was the right choice, because it was awesome. Did you know that Ghengis Khan is directly responsible for the invention of passports, priority mail, and pants? PANTS! He was awesome.

We walked around seeing as much as we could before they announced that the museum was closing. When we left it was sprinkling again, so we went to go see if we could get on the water taxi. It wasn’t the best day for it, but we figured we probably wouldn’t have time before leaving on Monday. The boat was just leaving as we arrived, but we got tickets for the next one in half an hour. We managed to find the only dry bench under a tree out along the waterfront, which was good since it started raining a lot harder. Our umbrellas kept us mostly dry.

We hopped on the water taxi and rode to Navy Pier. I’d like to do this again sometime when it’s sunny, because the view is great:

Navy Pier was not at all crowded, since it was late in the afternoon on a very damp Sunday. The rain was coming harder, so we went to walk around inside the mall area. It’s basically like a cruise port, all souvenir tshirts with cheeky phrases on them, your name on a grain of rice, caricatures, and fudge. (Why is there always a fudge shop?) We walked up and down past the kiosks and then went into Harry Caray’s for a beer, thus ensuring it would be the most stereotypical Chicago trip ever (see: Dunkin Donuts, Portillo’s, and later Giordano’s as well).

We were hungry but didn’t want dinner yet, so we got pretzels and beer. I could see out the front entrance of Navy Pier from my seat, and it was now POURING. Everyone was huddled in the entryway not going anywhere. It was a good time for a beer and some sports on TV.

After a while, the rain was showing no sign of letting up (even though our phone-weather swore it was nice out). We decided to finish our beer and brave the weather rather than trying to wait it out any longer, since it could possibly go on forever. We stopped to get a picture of Bally with Harry first, though.

Navy Pier is nice enough to have a free shuttle that circles the River North area, so we walked a block to the stop. I was very glad for it, because it’s a long way to an L station from there. We rode to State Street and hopped off right across the street from Sable. (It was one of the cocktail bars on Matt’s list, and is run by one of the chefs we’d seen on Top Chef.) There was no problem getting seats at the bar due to the incredibly crappy weather, thankfully.

The bar was excellent, and we nerded out over the menu. I tried Swedish Punsch for the first time, and got a cocktail with it. We had a couple drinks and hung out there for a while, and FINALLY the rain started to let up a little. We got our tab and walked north the six or so blocks to Giordano’s.

I know how it works with Giordano’s… you order what you think is a very modest pizza, and you end up dying of fullness and regret over not being able to have more. So we decided to get a bruschetta appetizer and a small stuffed pizza. You kind of need an appetizer if you’re hungry at all, since the pizzas take at least 45 minutes. Their bruschetta ended up being more of a loaf of bread, but it was really good. We got a Goose Island pitcher and hung out for a while.

Our small pizza arrived, but it was still gigantic. I ate one piece and couldn’t handle any more. Matt made it through two. We still had more than half the pizza left, and couldn’t even touch it. The server didn’t seem to want to let us leave without it, but it wasn’t going to make a great carry-on. Farewell, delicious pizza! You served us well.

We walked back south a few blocks past Sable, to Andy’s Jazz Club. Matt’s parents had taken him there as a kid, and it seemed like a good late-night Sunday option. We got a table and watched the jam session that was going on. It was all people who knew each other there at the club, and they swapped out every few songs. I learned a lot about jazz, because I never really know how the improv thing works. When a 15-year-old girl got up and played the piano with the band, we couldn’t believe it. Amazing.

Around 1 or so, we decided to head out. It was less than a mile to the hotel, so we crossed the river (past my favorite buildings) and walked back to the Palmer House.

The next morning, we slept in til 10, then checked out of the hotel. We left our backpacks with the bell desk and hopped on the blue line to Logan Square. Our brunch destination was Lula Cafe, conveniently located a block from the station. We both had excellent food and cocktails, so it made the immense hipster pretentiousness of the place more tolerable. Plus the people-watching was hilarious: I’ve never seen so many pairs of high-waisted shorts and fake glasses in one place.

We rode back downtown and walked to Millennium Station to get the Metra to the Museum of Science and Industry. We had to wait about 20 minutes for the train, and we knew our museum-time would be limited, but that was fine. I love that place.

The ride took only about 15 minutes, and the walk to the museum was a couple of blocks long. Which was good, because it was really hot out again.

We did the whirlwind tour, making sure to visit all the old favorites. The U-Boat had moved since last time I was there, and everything looked very updated. I recognized most of the exhibits, but not the areas surrounding them (except for the main hall).

I’m glad the chick hatchery is still there. It’s my favorite!

We had to head out by 4:30 to catch the train back. We didn’t have a ton of time at any one exhibit, but we covered a lot of ground anyway. We rode back to Millennium Station, walked to the hotel to get our bags, and then went to the blue line to ride back to O’Hare.

We had enough time there to get sandwiches and eat quickly before the flight, but we did so extremely dejectedly since we 1) didn’t get upgraded to first class and 2) didn’t get $800 from Delta this time. (Ok, I lied about the dejected part.) We had a good flight back, and were home in time to catch up on Breaking Bad before heading to bed!

We left town around noon and tore out of town. We arrived in Chicago around dinnertime, checked into our hotel near the airport, and then headed into town. We hadn’t counted on the ridiculously insane traffic, so we were near starvation when we finally arrived.

We’d planned on Kuma’s Corner, but there was a line out the door, so we chose Abbey Pub instead. Matt need to try their curry fries, anyway.

After eating and watching some baseball there, we headed over to give Kuma’s Corner a try. We were way too excited that they had Buffalo Trace (that’s bourbon, for those not in the know) on tap. The place was still insanely crowded, and at least 150 degrees inside, but it was still awesome. We managed to fight our way to the bar to order, and grabbed a couple of sittin’ spots on the front windowsill. We’d put our names in for a table, but decided to leave long before they came up. Before we left, though, we found this in the bathroom:

We decided to head down to Wicker Park, near Lauren’s work, so we could meet up with her when she was done at 1am. We found a spot after much searching, and then had to stop in to pick up a parking pass from her, because god forbid you just park on the streets in Chicago. The good thing was that we could leave the car there overnight, if necessary.

The streets in Wicker Park were crawling with a hipster infestation. Their numbers were kind of unbelievable. I’ve never seen so many kids who all look exactly alike while at the same time believing themselves to look very unique. We rushed through the thronging masses in search of the Violet Hour, which was owned by the same people who run Bradstreet 601 here in Minneapolis. It’s a bar known for very creative mixology and awesomeness, and we knew we could count on Bradstreet’s recommendation.

Having the address for the Violet Hour was no help; we realized that most likely it was the plain, windowless, whitewashed building with a single yellow light over the door, but we weren’t sure. We decided to go in anyway, and found a few people standing in a dark entryway, reading the rules for the place. They included things like ‘no cell phones’. There was dress code, too, though no one there was even close to fitting it. We didn’t, either, but we figured that must be ok.

The host came in shortly and grabbed Matt and I, the lucky party of two who got to go ahead of everyone else. He asked if the bar was OK, and obviously that was what we preferred anyway. The cocktail standards at the Violet Hour were definitely the same as Bradstreet, though it was a little disappointing that they were way too busy to have a conversation with any of the bartenders. That’s one of the best parts.

We left a bit later, and still had some time to kill before meeting Lauren. We decided that food was the best choice, given our current state, so she pointed us toward Flash Taco down the street. It was bad; slow, packed with hipsters, and the food was terrible. Based on about three hours of experience with it, we decided that Wicker Park sucked a lot. Regardless, I’m pretty sure we’re right.

Finally, Lauren was done with work. We met up with her there, and went to the nearest bar, directly across the street. The Flat Iron seemed to be an exception to Wicker Park’s lameness, or at least there were enough non-hipster people in the crowd there that it was tolerable. We had an awesome time.

Round about… well, I really have no idea. 3am? 4am? We walked Lauren back to her apartment, stopping at Dunkin Donuts on the way. I think I ordered three beverages. Matt and Lauren had them some very patriotic donuts!

We made it back to the hotel after 5am, and crashed. It had been a very long day.

We got up at the crack of noon (haha), and got ready to head downtown. We were smart this time, and took the hotel shuttle to the train station at O’Hare. It was a big day!

We intended to go to Hot Doug’s to get some food, so we hopped off the train at the appropriate stop and headed east. Most people would’ve taken the bus, but we insist on walking. After a mile or so, we arrived to find a line two blocks long. I’m sure Hot Doug’s is awesome, but we couldn’t wait that long.

So we kept walking. And walking. I have no idea how far it was, but it was a lot. Finally, we found ourselves at Wishbone, one of my favorite places. It was 3pm. Perfect time for brunch, if you ask me.

We revived ourselves with lots of coffee and grits, and then headed up to hop on the El. Someone on twitter had told me about the crazy paintings at the Old Town Ale House, so we had to check that out. Well, the paintings were amazing. How can you go wrong with creepy naked Sarah Palin? The bar itself was kind of scary, though: we walked in and everyone turned at stared. That’s because everyone else lived there, and we were strangers. At least the bartender was nice!

We rode downtown and walked over to Millennium Park, because no trip to Chicago is complete without a visit to Cloud Gate, aka the Bean. There were Honduras soccer fans everywhere. So awesome.

We still had a bit of time to kill before the game (and we were alarmingly sober), so we set off in search of Matt’s dad’s favorite bar. It was easy to find, and was crowded with fans. We found spots at the most oldschool bar ever, and I ordered a Manhattan and a piece of spanakopita. That’s just how I roll.

Matt went out to smoke, and came back in with Robin in tow. He’s one of Kris’ friends, and we run into him at every soccer-related event in Minneapolis. We finished our drinks and decided to head down to Soldier Field.

Even though I grew up in Chicago, I’d never been to Soldier Field!! It’s amazing, and so was the crowd.

There were a few sections of US fans at either end of the stadium, but it was at least 80% Honduras fans. That was a little intimidating, but the atmosphere seemed friendly. The US fans seemed to be doing most of the taunting, of course.

We got to see Landon Donovan:

And Jozy Altidore:

And, of course, Tim Howard. I love Tim Howard. A lot.

The game was pretty stressful, but the US team managed a win! Towards the end, some of the Honduras fans in the upper deck started throwing their beer cups onto the US fans. We were pretty glad to be in a sheltered area.

The entire crowd poured back into Chicago together. Despite the taunting and such at the game, everything was very friendly again. It was also the only time I’d be comfortable chanting “U.S.A.!” Usually that kind of behavior makes my skin crawl.

It was worth it for the deep dish.

I was pretty much dragging at that point. We wanted to go hang out somewhere for a bit, but didn’t want to make a lot of effort doing so. Thankfully, the blue line helped us decide; it was closed for several stops between downtown and O’Hare, so we decided to take the shuttle up to the part where it was back in service, and find somewhere to drink right near the stop. Then getting back on the train and to the airport when we were about to fall asleep would be as easy as possible.

The offerings at that stop looked a little bleak when we got there, but we managed to spot a couple places, and decided on the one called the Green Eye. This, it turned out, was the right choice.

The crowd reminded me of a cross between Grumpy’s and Triple Rock, which was immediately appealing. The bartender was gruff and hilarious. After we’d had a drink or two, he came over and excitedly started telling us about the movie they were about to play; apparently they have a trashy horror-film tradition on Saturday nights. It was called Poultrygeist, and it was a Troma musical. Rather than try to explain it, you should just go read about it.

Poultrygeist was as great as it sounds. The entire bar sat there watching it, breaking into hysterics and groans. We really need to get a copy so we can spread the love.

Eventually, Matt and I made our way back over to the train, and from there to the hotel shuttle stop at O’Hare.

Sunday morning, we got up bright and early and headed out for the most important Chicago tradition. It doesn’t matter that I don’t eat donuts; they many awesome breakfast foods. And good coffee.

We did some shopping at CB2, one of my favorite stores, and then it was time to head homeward. With a stop for lunch at the Great Dane in Madison, of course!

I miss Chicago! We used to go there all the time. That high-speed train between there and the Twin Cities needs to happen.

[To view the entire Flickr photoset from this trip, go here.]

Wendy, Willis, Matt and I piled in Matt’s car and rushed the hell out of town on Thursday after work. We didn’t get on the road til almost 7, but we had nothing to do but get to Chicago that night.

At one point, Matt had to decelerate from 72mph because he was so caffeinated he was seeing through time. We got to the hotel around 2am, and jumped into bed as quickly as we could.

We got up Friday morning and searched in the phonebook for the nearest Dunkin’ Donuts, because what you’ve heard about their coffee is true. We headed downtown and had a brief rendezvous with Lauren outside her work, because she had obtained a parking pass in her neighborhood and some 24-hour CTA passes for us to exploit. We drove up and parked by her house, and took the bus to Wrigley Field.

wendy found herself some reading material on the bus.

We got there really early, so we wandered around the store for a while, then crossed the street to the Cubby Bear. Of course we had to try the Cubby Blue Bombs for $4 (it made my stomach hurt for the next five minutes). The Sparks girls were there handing out samples, and of course we had to try that, too. It wasn’t great, but it was free. They came back around later asking if we liked it, and wanted free cans. Um, yes.

I lived in Chicago for ten years growing up, and had never been to a baseball game there. In fact, I’m pretty sure I’ve never been to any sporting event in Chicago. I was only really interested in Wrigley Field, though. It was great.

Our seats were in the second row from the top, but they were awesome. I’m glad we weren’t in the bleachers, because the sun was brutal. Our row-neighbors were from Oklahoma, and I’m pretty sure they’d never been to a baseball game before; one of them got up and made us stand up so they could wander around at least every 15 minutes. They couldn’t even go as pairs.

We got to see Luis Castillo, who the Twins traded to the Mets a few weeks ago, and also Eddie Vedder singing “Take Me Out to the Ballgame” during 7th inning stretch. (Pearl Jam was playing at Lollapalooza.) I had flashbacks to 12 years ago. Also, I was excited to realize that you can see Lake Michigan from the ballpark.

The game was going well until the last inning, when the Mets scored about 500 runs. I’m not joking.

the ‘lose’ flag

We killed some time wandering around the stadium, then went to the el station. It was still crazy, but we managed to get on the first train and ride downtown to Millennium Park.

crown fountain

We had decided upon deep dish pizza much earlier, and there was a Giordano’s a few blocks up Michigan Avenue. We walked over there and found it very crowded. While Matt and I waited in line, Willis looked up another location in downtown. He called them and they said there was no wait, so we headed over that way.

After eight blocks or so, we realized that Google Maps had lied to us, and the restaurant was still several blocks from there. We ended up walking very far for that meal, but it was worth it. Not only was the pizza awesome, Franz from the Hold Steady was sitting at the next table.

We were rerouted along the way back to the train station because they had cordoned off a large section of downtown to film a movie. We asked a security guard what it was, and he said, “Batman.” We weren’t sure if that was true or not, because there was a production assistant across the street telling people it was Rory’s First Kiss. Willis looked it up, and it turns out that’s the supersecret working title for the new Batman movie. Wendy decided to stay and film some scenes.

wendy on the batman set

We got lost trying to find the el station for a while, and had to call Lauren for help. We rode up to her house, and walked over to Louie’s, the karaoke bar we’d visited the first time I stayed with her.

The karaoke was awesome but the drinks were not, so we headed to a dive called the Beachwood instead. Upon close, we went for 2am breakfast at the Hollywood Grill. It was not great at all, but it was necessary. We didn’t get back to the hotel til 3:30.

We arose very late on Saturday morning, got us some giant coffees at Dunkin Donuts, and headed toward my old hometown of Wheaton. It’s a tradition to drive through and see it every time I’m in the area.

i lived here for grades 1-5.

We drove through my old neighborhood and cute little downtown Wheaton, which is scarred irreparably by a Starbucks. We then headed to Portillo’s for lunch. I was thrilled to see that they now have a veggie sammich.

Very sleepy from lunch, we made our way into Wisconsin, with a quick stop for gas and naked ladies.

We checked into the hotel and then headed back out to pick up tickets, Wendy’s friend Rick, and grilling supplies. We arrived at Miller Field a mere hour or so before the game, in the rain, but this did not prevent us from getting our awesome tailgate on. We had plenty of company there, too. Milwaukeeans know how to party.

willis drinking a 40 from a plastic bag

that’s leftover deep-dish pizza on the grill!

wendy with a yard of berry weiss, smoking strawberry and tequila swisher sweets at the same time.
and she’s wearing a cape. yeah.

Post-tailgate, we headed toward the stadium, but were diverted at the Sausage Haus. We went in to use the restrooms, and they were blasting ‘Party Like a Rock Star’ at ear-bleeding volumes. We didn’t know it then, but this was some serious Wisconsin foreshadowing.

Miller Stadium is amazing. It has a retractable roof (which was closed due to rain, but that was alright), and is designed really well, in a way that makes me very excited for the open-air stadium here. Also, they have sausage races. We saw two of the sausages going up in the elevator, both leaning folded-over on the people in there with them. It was hysterical.

We found our seats and somehow ended up drinking Sparks again, for reasons only Wisconsin understands. Round about the fourth or fifth inning, Willis and Matt and I got up to go to the bathroom, and then decided to check out the outdoor bar. It was there we met Bobby Chicago and his girlfriend, the people sitting next to us at the game. Bobby and I both grew up in Wheaton, and he told me how everybody thinks he’s hardcore because he’s from the 187 (the zipcode is 60187). They introduced us to the Captain Bomb, and we possibly didn’t realize how long we were out there until Wendy texted, wondering where the hell we were.

We went back inside just in time to catch the sausage races and the end of the game. The Brewers had a pretty spectacular win, and we stuck around for a bit afterward watching to see if the Cubs fans who showed up just to aggravate the crowd would get their asses kicked. There were a couple people escorted out by the cops, but that’s about it. Also, it’s pretty funny to see the difference in the baseball crowds between Chicago and Milwaukee. As we all know, Wisconsin = booze.

We made plans with Bobby Chicago to meet up after the game, and headed to the store to shop. We stopped again at the Sausage Haus on the way back to the parking lot, and this time I found Wendy a son. He was laying on the floor under the sinks on one of those little-league photo buttons. She named him Jacob.

Since there was a line of traffic waiting to get out of the lot (admittedly, a very short line, but we’ll take any excuse), we decided to continue tailgating for a while. We ended up blasting Minneapolis hiphop with all the car doors open and dancing in the parking lot. After that, Rick drove us to the Safe House.

I cannot really express how awesome the Safe House is, so you should probably just go. We all whispered the password and passed our $5 to the girl in the entryway, happily escaping the customary televised ridicule of people who had never been there.

We shared a giant drink called the Mission Impossible, explored as much of the place as we could figure out how to access, went in the sound-effects phone booth, touched Burt Reynolds there, and a couple of us may have gotten up to naughty bidness in the downstairs hallway. Possibly.

We finally found ourselves sitting next to the dance floor, and then there was dancing to things like ‘Save a Horse, Ride a Cowboy’ followed by ‘Crazy Bitch’ (best two-song playlist ever!), ‘Fergalicious’, ‘Sexyback’, and, yes, ‘Party Like a Rock Star’. The floor was so sticky that my flipflops kept adhering to it; I’d dance out of one of them, then have to dance back toward it to retrieve it again. There was a bachelorette party going on next to us, complete with a male stripper with his boxer-briefs on inside out (they dubbed him Skidmark). And there was also Black Derek, but I cannot possibly explain about that. All I remember was his shirt, and the fact that he was there dancing on the stairs with us.

I have no idea what time we got back to the hotel, because I was sleeping in the backseat most of the way there. I have vague memories of them getting lost, and apparently that did actually happen. Oh, Wisconsin.

Thursday night, Kaye joined la familia in celebrating Claudia’s birthday, and then we went to the airport together, but for different flights. I managed to have found one of the only on-time planes to Chicago, but she and Mollie were not so lucky. The guy in the seat next to me on the flight offered me his finished novel halfway through the very short trip; it was curled and puffed up to twice its normal size because he got to the most exciting part while on his boat, jumped in the lake, and the book followed him in. He was crabby about the fact that he had to take a hiatus from reading to let it dry out. We exchanged travel notes (he’d been to China recently, and I’d been to Alaska), and he said he’d look for me at Lollapalooza on Saturday. Um. Sure! I hopped the blue line with a crowd of other festival-bound folks, none of whom seemed to have a clue about Chicago and spent the whole ride worrying about where to go. I realized I must be a seasoned traveler, since I never really have any concerns about finding where I’m supposed to be: if I don’t know, that’s what people are there for. I exited at Division and heard Lauren yelling, “There she is!!!” even before I saw her.

We stopped at her place long enough to drop my stuff off and toast to Minneapolis with her roommate, then headed over to Louie’s for karaoke with her new cute punk-boy pal and his North Carolina friends who were also in town for Lollapalooza. It was SO FUNNY, and, due to the house drink known as the ‘blue motherfucker’, SO DRUNK.

kevin and roy singing karaoke at louie’s

We reeled home in hysterics at 2am, and I slept in my clothes.

Friday morning, I have no clue how Lauren got up and went to work, but she managed it. I slept in, spent time in the bathroom with Joe (I love that cat), talked on the phone a lot, then headed downtown to meet Kaye and Mollie. We headed into Lollapalooza, and the rocking commenced.

panic! at the disco

kaye and mollie stretching

raconteurs

My favorite bands that day were Panic! At the Disco (which featured burlesque dancers), the Raconteurs (because I love Jack White as it is, but Jack White in a southern-rock band? Drool.), and the Violent Femmes, because everyone loves the Violent Femmes. Afterwards, we met Lauren by the Bean in Millennium Park, and she and I headed to dinner at Bandera, a restaurant far too fancy for our dress (and my smelliness), but who cares?

Afterward, we met up with a dude named Walt at Watertower Park, stormed through the crowds of date rapists lining the streets of Chicago, and hopped a bus to what Lauren promised to be the most annoying hipster bar in town, the Rainbo Club. She was right; we couldn’t move more than ten feet from the doorman, it was so crowded. And smoky. And pretentious. We actually talked to a few dudes who were pretty funny, but not funny enough to make us stick around longer than a drink. We bailed around one o’clock and headed off to find another spot, finally deciding on Subterranean, when Lauren ran into a friend of hers nearby. We hung out with him for a while, then headed home.

Lauren and I got up Saturday and went to have brunch at the Bongo Room, which was excellent. We also bought me some sunglasses, which I still have to this day. That’s a new record, and I probably just jinxed it.

me in the bathroom at the bongo room, with amazing sunburn.

We saw several shows Saturday, but the one that I’d have paid the entire ticket price for was Lyrics Born. Mollie and I got there early to get a spot near the front, ending up about three people back.

lyrics born. i love this man.

By halfway through the show, I was against the railing, and totally fucking thrilled about it. I emerged from the show drenched in sweat and gasping for air, my camera chock-full-o-videos that I should probably post somewhere to share the awesomeness. Afterwards, I stuck around for Blackalicious, and was surprised at how much of their music I still knew. I was also giggling inside at the conversation the kids were having next to me: they basically discovered hiphop that day.

blackalicious

I met Kaye by a pole for half of the Dresden Dolls, and then took off on a mission: to get Lauren at the station and go find a little bit of Minneapolis in Chicago. She told me to hop in the last car so she could find me at the Damen stop, only I got turned around and got in a car very near the front instead. At each of the next four stops, I’d hop out of the train, run as far as I could before the doors began to close, and then hop into another car further down the line. I really hope no one knew what I was up to, because it was comical. But I did finally achieve the last car, met up with her at the correct stop, and we were on our way to the Abbey Pub to see P.O.S..

We got there early enough to get dinner, including curry fries, which are good enough to fantasize over, oh my god. We heard the sound check finish, the side door opened, and P.O.S. walked in. I almost peed my pants with excitement. But of course, there are like two people in the universe I’m too intimidated to talk to, and he’s currently one of them. We met some boys in line who were excited that I was from Mpls, and one of them was convinced he’d seen me at shows, so we compared notes. We went in and talked to Sims and Cecil Otter at the merch table about Hiphop and Harmony and Lollapalooza, and then the COMPLETE AWESOMENESS OF THE SHOW BEGAN.

the aristacats

mictlan

doomtree!

p.o.s.

artist outside the show

It was so great I can’t even really describe it, except that it involved a lot of yelling and dancing and jumping around and whiskey and picture-taking, many of which you will find in the usual place. I have more videos as well. P.O.S. rocked our pants right off, and I daresay Lauren the punk girl might even be a new hiphop convert. At least a little bit. After the show, we went back and talked to them some more, I was still too intimidated to do much but shake P.O.S.’ hand, we met Psalm One, and some people left with my number we can hang out when they’re in town for Atmosphere at the end of September. All in all, the best show ever, yet again.

lauren

We hopped a cab back to Lauren’s neighborhood and stopped at 7-11 for large bottles of water, which shared the bed with us that night.

Sunday morning, we got up and went downtown to Millennium Park to take about 400 photos of the bean, aka the Cloud Gate. I could probably stare at that thing all day. We sat and watched the kids in the fountain, then wandered back into downtown to find food. We found Kaye and Mollie there, so I headed back to Lollapalooza with them.

I was very excited to see the Hold Steady with their many many Minneapolis shout-outs (and also the fact that Craig had shown up to perform with P.O.S. the previous night at the Abbey). My second-favorite show was Queens of the Stone Age, although the Kids from the School of Rock kicked ridiculous amounts of ass for being so young.

the hold steady

In the evening, Lauren and I went to Piece (aka the Luce of Chicago) for dinner, and for a short while it seemed like a really great idea to go out after that; however, by the end of dinner, we were both dragging. I was sore from the walking, the rocking, the sunburn, and the general awesomeness. We went back to her place to hang out, and then I passed out hard.

On the flight home Monday, reveling in another first class upgrade with my legs curled underneath me on the seat, having survived a very large drop over Lake Michigan which went unexplained by the cabin crew but did not leave us entirely unrattled, I was peering down at the immense patchwork of farms in Wisconsin, remembering that I leapt headfirst towards that the other week wearing nothing but a hot guy with a parachute, and I was a grinning fool. And then I realized that for the rest of my life, I’ll always have had more takeoffs than landings.

I think that’s a really beautiful metaphor.