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.