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.
The Purple Pig
๐444 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!
Lou Malnati’s Pizzeria
๐439 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 ร la New York City, but this was a must-try while in Chicago.
Portillo’s Hot Dogs
๐100 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.
Alinea
๐1723 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.
Do-Rite Donuts
๐233 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.
Twin Anchors Restaurant & Tavern
๐1655 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.
Roister
๐951 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.
The Aviary
๐955 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!

Food is definitely one of the reasons why I would love Chicago. When it comes to dining out, vegetarians are often left with limited options, but not in Chicago. The list of various vegetarian/ vegan restaurants offering deliciousness powered by plants is very impressive. I would love to try out the donuts, too, they look so yummy. Thanks for sharing and have a good day. Aiva xx
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It does seem tough to travel as a vegetarian/vegan but the great thing about visiting metropolitan cities like Chicago is that you’re sure to find some good options.
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22 courses is a lot! Not sure I’ve had more than 3 haha. I love Giordanos pizza the best in Chicago ๐
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Haha, they were 22 bite size courses (tasting menu) so manageable. I havenโt heard of Giordanos; will have to check it out the next time Iโm in Chicago!
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On the contrary, I’m a deep-dish pizza lover all the way…which is why I’d love to go to Chicago to get the dish from where it originated! That buttermilk doughnut looks crusty and divine, perfect for dunking in coffee or tea. Looks like quite the food adventure you had in the Windy City!
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Lou Malnati’s and Giordano’s seem to be the top choices for deep dish pizza in Chicago, so keep those on your list for the future visit ๐
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Totally agree that Chicago is a haven for foodies. Best pizza in the world! we took ours at Giordano’s.
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You’re the second person to recommend Giordano’s. I will have to check that out if I make it back to Chicago someday.
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Wow I’m envious of the amazing food experience! I lived in Chicago right after college for a bit, and that fresh out of college budget (or lack thereof) prevented me from diving into the amazing food scene. I am convinced that I certainly need to pay the Windy City another visit ๐
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We definitely splurged on the food during this trip!
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Delicious. I used to live in Chicago. You ate at all the right places! Purple pig was a favorite of mine!
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Yes, that bone marrow from Purple Pig was the best!
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I need to stop reading food blog posts. I’m incredibly hungry now. The ribs, the duck, the pizza, and basically everything looks super delicious.
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Hehe, thanks for reading!
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The deep dish pizza is so good there. I miss that.
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A Chicago classic. Thanks for reading!
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Love Chicago and all its fine restaurants. Youโve inspired me to add a few more to my list. Iโve been to The Purple Pig and loved it!
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Chicago has endless restaurant options but deep dish pizza has to be tops. Thatโs probably my favorite kind of donut too!
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Deep dish wasn’t my favourite but it was still good, along with all the other great stuff we ate in the city. Thanks for reading!
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I’ve always wanted to go to Chicago for the food! That pizza there is what dreams are made of!
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Chicago deep dish is a mandatory part of every foodie’s bucket list ๐
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As a former tourism director of the great state of Illinois, I approve this message! You’ve got a great roundup of places here. I think one could write an entire blog post about the food destinations in Fulton Market alone, right? And I’m so glad that you made it to both the Aviary and Alinea. Those are really special dining destinations. Well done!
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I didn’t even get a chance to fully explore Fulton Market. There’s a lot more to eat when I return to Chicago!
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It all looks so delectable, especially the donuts, pizza, and duck breast. Your picture of the deep dish pizza has me questioning whether to dive into ours (there’s one in our freezer from a local restaurant – just doing my part for small businesses during the pandemic ๐ ) this weekend, or save it like I had planned. Decisions, decisions…
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Do it! Mmm, pizza ๐
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woah some nice looking food there! The pizza looks so tomato-y which I love! And the ribs looks pretty darned good!
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Yes, those ribs were gooood!
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We love Chicago and all the food! Definitely pinned this for the next trip, it all looks incredible and a Michelin starred restaurant is on our itinerary!
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It was all delicious and there’s so much more food to try in Chicago. Thanks for reading!
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It looks like you had a full and filling stay. We only had early mornings to see and taste Chicago as we spent each day at a three day rock festival. Still yet to have one of the hotdogs, enjoyed the pizza, and it seems like you found some pretty cool foodie places to try!
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I did have a very filling stay! I’d love to go back to Chicago someday. There’s still a lot more to eat ๐
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Mr. Beef on Orleans is THE place to go for Chicago Italian Beef!!
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I’ll have to look that up!
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Next time try Ginos east you will have a new favorite. And if you like sausage try the sausage patty it covers the whole top of the pizza. Far better then giordanos trust me. I hit ginos when ever I visit from Florida
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I was able to do a โstageโ for a day at Alinea because a fellow culinary school classmate worked there. Those chefs work so hard every day, all day. My favorite deep dish is definitely Ginos East. The difference is their use of cornmeal in the crust. I have even found it frozen in Michigan where I live, and itโs very good surprisingly. Iโve heard great things about Pequods too, but have yet to try it yet.
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What an interesting experience it must have been to spend that time at Alinea!
It seems that the debate on the best deep dish in Chicago is an everlasting one. You’re the second person to recommend Ginos though.
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What a fun trip! I went to Chicago for the first time in November 2019. I didn’t have enough time to eat all the recommended foods, but I did have Lou Malanti’s pizza and Portillo’s hotdogs. Your article is a good reference for my next trip there. It is a fascinating city! Thanks for the suggestions.
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It was fun! Chicago is an awesome food city.
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