The Coffee Person’s Guide To Hanging Out In Chicago


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As many of you plan your visit to Chicago for the annual Specialty Coffee Expo, you might be daydreaming about everything you’ll do outside the convention hall’s walls. 

Yesterday, I gave you a list of coffee shops I think you should check out, and today, I want to recommend a few things to consider when traversing the city. This year’s Expo takes place at the McCormick Place Convention Center, which offers us a lot of room to play: the convention center is right on the water of Lake Michigan, is close to two of the most exciting food neighborhoods in the city, and is only a few miles away from where the Chicago White Sox play (you better believe I’m going to recommend going to a baseball game while in the city). 

This list will primarily include restaurant recommendations, focusing on spots in Chinatown, Pilsen, and the South Loop. I’ll also try to highlight places with outdoor seating for people who’d prefer to dine outdoors (this might be subject to change based on weather). I also want to encourage you to see some of the fun stuff Chicago has to offer, so I’ll make recommendations on things I think would be worth your time. 

As I mentioned in my coffee guide, I am not an expert—my list is highly subjective and reflects what I like to do in Chicago. But I hope this helps you navigate what is easily the best food city in the US (come at me, New York) and some of the fun things you can do with a few spare hours. 

The McCormick Center is close to two incredibly notable food neighborhoods, Chinatown and Pilsen. You could spend your entire visit dining solely in these neighborhoods. Three of my favorite spots in Chinatown are Qing Xiang Yuan Dumplings (they don’t accept reservations, but you can queue in line remotely, which I recommend because this spot gets busy), Joy Yee, and Lao Sze Chuan. But really, you should go and enjoy the neighborhood. Chinatown is highly walkable and serviced by the Red Line. 

Pilsen is a traditionally Mexican neighborhood and artist enclave but has seen significant change due to gentrification. However, there are still so many amazing spots to visit, and the neighborhood is also very walkable. I love Taqueria Los Comales, Birrieria Reyes De Ocotlan, Carnitas Uruapan, La Chaparrita Taqueria (this is technically in Little Village, a neighborhood just west of Pilsen), and La Esperanza. Hang out at the Skylark for drinks: the bar has been in the neighborhood for years and was recently purchased by the bar’s longtime employees after the owner decided to retire. Get a basket of tater tots. 

I still seek out restaurants with outdoor seating, and you have many options in Chicago (let’s hope the city decides it’s spring for good). The Duck Inn, Maria’s Packaged Goods and Community Bar, and Pilsen Yards are somewhat close to the convention center (close might be subjective—please Google distances before you pick a place!) 

If you want to explore a patio or outdoor seating space a little further away from the convention center, I cannot recommend Irazu more (a Costa Rican restaurant that I’ve been going to since I was in college), The Frontier, Cindy’s Rooftop Bar (for you Top Chef heads, obviously the city has so much to offer, but a contestant on this current season is the chef at Cindy’s), Rootstock, a wine bar with a late-night menu, Ina Mae Tavern (I ordered my Thanksgiving meal from here during the first year of lockdown), and Small Cheval (the original Au Cheval is very popular, but I prefer Small Cheval’s original location in Wicker Park, which just serves the original restaurant’s signature burger and has picnic tables outside). 

Although not technically an outdoor seating area, it’s customary to order from Calumet Fisheries, sit in your car, and eat while parked. Keep an eye on this spot—it had to close due to extensive fire damage but aims to reopen in April. This is a place I stop at every time I’m in Chicago.  

If you’re looking for more sit-down options, on the top of my list are Virtue, Mi Tocaya Antojería, Superkhana International, Lula Cafe, HaiSous (this is closer to the convention center), Kasama (see our coffee guide), Soulé, and The Publican (get the chicken). The Publican is located in a neighborhood called the Fulton River District, and it’s sort of a “hot spot” for restaurants—if you walk around, you’ll find somewhere to go. 

Ok, it’s time to talk about pizza. Yes, Chicago is known for deep dish style pizza, but there are so many fantastic pizza spots in the city that go beyond deep dish. If you’re dying for deep dish, go for Pequod’s (my favorite, also seen in the Bear). But I’d urge you to try all the amazing non-deep dish spots like Middle Brow (an incredible brewery as well, and they have outdoor seating), Pizza Lobo (outdoor seating), Bonci (great for a quick lunch), or check out tavern-style pizza (re: thin crust, cut in squares). 

Chicago is full of classic food stops like Johnnie’s Beef (although be ready for a trek), Redhot Ranch, Harold’s Chicken Shack, Valois, Vito & Nick’s (see above about tavern-style pizza), and Portillo’s. None of these are overrated in the slightest. They are worth the visit. 

So now you have a zillion restaurants to choose from. Let’s assume you have at least some free time: go to a baseball game. When I went to my first Expo in Boston in 2013, I went with a group of people to see the Cubs play, and it’s the only thing I remember doing from that entire trip. McCormick is just a stone’s throw away from where the Chicago White Sox play, and it’s just a fun place to hang out, grab some fresh air, and relax. Although basketball tickets are much more expensive than baseball, the Chicago Bulls play their last three games of the season at home (this is where you’d find me). 

Sure, go visit the Bean, but also go to the Art Institute of Chicago. You’ll never get to see the entire museum, so accept defeat before you walk in and make a plan based on how much time you have. The whole collection is lovely, but make time to see Nighthawks, Nightlife, The Old Guitarist, A Sunday on La Grande Jatte, and American Gothic.  

Go on a riverboat tour. The first thing I did on my first day in Chicago was a boat tour exploring Chicago’s architecture, and I still think it’s one of the most enjoyable things I’ve ever done. Not only do you get to check out beautiful buildings, but you also get a unique look at the city by floating down the river and seeing just how stunning Chicago is. 

I hope you all have a great time in the city!

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Ashley Rodriguez

Ashley Rodriguez is the managing editor at Fresh Cup. She served as the online editor of Barista Magazine from 2016-2019 and is an award-winning beer writer and podcaster. She hosts a podcast called Boss Barista and writes an accompanying newsletter about coffee and service work.

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