When we visited Chicago in 2018, we had the chance to marvel at its world-famous architecture and scope out its top landmarks, but the part of the trip we were most excited for was the food. Chicago has been voted America’s top foodie destination in various publications — and based on our five days of gluttony in the Windy City, I would agree with this designation. From the classic deep dish pizza to molecular gastronomy at a three star Michelin restaurant, Chicago has a massive range of good eats. Here’s a recap of all that we managed to fit into our stomachs during our short visit.
📍444 Michigan Ave, Chicago, IL 60611
Dinner at The Purple Pig was our first nutritional stop in Chicago. This James Beard and Michelin Bib Gourmand winning restaurant is located off the Magnificent Mile, serving shareable plates of Mediterranean inspired dishes. Our favourite selection was the bone marrow with herbs and capers. This was a huge meal that gave us the first inkling that everything is truly bigger in the Midwest. A similar tapas restaurant like this in Toronto, such as our beloved Bar Isabel, would have portions about a quarter of the size of what they served us at The Purple Pig. Our server suggested 5-6 plates for the two of us, which perhaps would have been appropriate if we were competitive eaters aiming to hit the morbidly obese BMI score. I’d say that a single plate would have been enough as a small meal for the average person!
📍439 N Wells St, Chicago, IL 60654 (and other locations)
Chicago-style deep dish pizza is prepared by baking the pizza in a deep pan, allowing ample space for loads of gooey cheese and chunky tomato sauce. According to Wikipedia, the origin story of Chicago deep dish is a bit convoluted, but it has possibly been around since as early as 1926. Opened in 1971, Lou Malnati’s remains one of the oldest family names in Chicago pizza. We stopped by one of the locations for lunch after our morning exploring Millennium Park and ordered their Chicago Classic with sausage. To be honest, I much prefer thinner pizza crusts à la New York City, but this was a must-try while in Chicago.
📍100 W Ontario St, Chicago, IL 60654 (and other locations)
Now, Chicago hot dogs are something I could eat all the time. The key features of a Chicago dog are the toppings of mustard, sweet pickle relish, dill pickle spear, celery salt, and tomato slices but no ketchup. Portillo’s was our favourite find for this Chicago staple, followed by Wrigley Field while watching the Cubs home opener. We tried to recreate Chicago dogs with our own recipe at home, but they were never quite the same as the ones in the origin city.
📍1723 N Halsted St, Chicago, IL 60614
Our most highly anticipated meal in Chicago was, without a doubt, at three Michelin Star Alinea. I’ve written about this restaurant in the past, and mentioned that it was one of the most interesting dining experiences I’ve ever had. Alinea serves a 22 course tasting menu of molecular gastronomy, including artful creations that integrate taste, scent, and visual tricks. The food was amazing, but it was really the interactive aspect of the experience that made it special.
📍233 E Erie St, Chicago, IL 60611 (and other locations)
The morning following our fanciest meal of the week, we went for a humbler stop at Do-Rite Donuts. This Chicago-based chain has made it onto several “Best Donuts” lists, best known for their small batch donuts created by Chef Jeff Mahin — who previously worked at two Michelin Star restaurant L2O in Lincoln Park. I recommend the buttermilk old-fashioned. They also serve Dark Matter Coffee here, another Chicago grown business.
📍1655 N Sedgwick St, Chicago, IL 60614
In search of dinner before a show at Second City, we came across Twin Anchors in Old Town. This tavern-style restaurant has been around since 1932, serving their signature baby back ribs, which we enjoyed with a side of Idaho baked potato. Apparently, this place was frequented by none other than Frank Sinatra beginning in the 1950s, and has since hosted several other celebrity visitors, whose photos line the walls inside. The restaurant has received a great deal of publicity over the decades, and I would say that the ribs here are certainly as good as advertised.
📍951 W Fulton Market, Chicago, IL 60607
We gave Grant Achatz a lot of business during our trip, as we also visited the sister restaurant of Alinea on our last evening in the city. Roister is the casual offshoot of the Alinea Group, specializing in creative New American cuisine. We particularly enjoyed the meaty duck platter of duck breast, tongue, tartare, hearts, and sausage. The signature dish here, however, is their whole chicken, served poached and fried.
📍955 W Fulton Market, Chicago, IL 60607
We followed our hearty meal at Roister with swanky drinks at the adjacent Alinea Group cocktail lounge, The Aviary. This place was very cool, featuring an extensive menu of creative alcoholic concoctions. I had a relatively simple apple brandy and vermouth cocktail with apple ice balls, while our friends tried out some of the more elaborate creations that almost looked too fancy to drink. Cheers, Chicago!