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Chicago, Illinois: 10 Food Stops During Your Trip to Chicago

I remember being a first grader trying to sit still in my squeaky desk. As I worked to pay attention and look at the board, my teacher yelled at me to stop squirming and squinting (the year was 2000, and apparently we still didn't think kids needed glasses?).

It was still a good day though. Why? It was Monday. It was pizza night.

Every Monday growing up was pizza night and, understandably, that made it the best night of the week. Chicago deep dish pizza became my favorite food, which I was told I would grow out of and never have. This is a pretty famous dish for Chicagoans, but it doesn't stop there. Chicago is full of rich, hearty foods---we are midwesterners, we need fluff to make it through the freezing winters. On top of that, Chicago has grown into an impressive food-filled city, with 25 Michelin-starred restaurants and more breweries than any metro area in the United States.

Ballparks, skyscrapers, diverse neighborhoods - Chicago has it all.

Here is a list of some classic Chicago foods to try during your visit...

1. Devour Some Deep Dish Pizza

What is different about deep dish pizza?

Picture something more like a pie. It has a high-walled crust and is filled with all the toppings you want, melted cheese, and topped (yes, topped) with red sauce & tomatoes.

Tell me more...

As mentioned, this is a must in my opinion. There is an ongoing debate: NY style or Chicago style. Well, I love NY style, but nothing beats a cheesy Chicago pizza pie. Another debate worth mentioning -- WHERE do you find the best Chicago pizza? My family is actually split; half of us think Lou Malnatis (including me) and half think Giordanos. The truth is, it's a personal preference, because everyone makes it a little differently. Some other famous places are Peqouds, Chicago Pizza and Oven Grinder (expect to have a long wait here), and The Art of Pizza (which sells by the slice). Why not just take a pizza tour and decide for yourself?

2. Eat a Chicago Hot Dog at a Game

What is different about a Chicago hot dog?

Well, mostly what it is -- and isn’t -- topped with. It IS topped with mustard, sweet green pickle relish, onion, tomato wedges, pickle spears, peppers, and celery salt, all placed in a poppy seed bun. It (very strictly) ISN’T topped with ketchup. No ketchup, people!

Tell me more...

I need to say it - go to Wrigley Field! There's no place like it. It is one of my favorite spots in the city. Here, not only can you grab some boozy drinks and catch some great Chicago views, but you can chow down on the best Chicago hot dogs while watching the Cubs win a game of baseball. You don't need to have ALL the toppings (although I suggest you do!), but for some reason real Chicagoans are offended by the idea of ketchup on a hotdog, so I might play it safe and leave it out this go-around.

3. Stop for an Italian Beef Sandwich

What is Italian beef sandwich?

A classic Chicago sandwich with thin slices of roast beef on a french roll. It is sometimes topped with peppers, cheese, and sauces.

Tell me more…

There are a lot of hole-in-the-wall places where you might be able to grab an Italian beef, but honestly most people enjoy the famous chain restaurant - yes, I am actually suggesting a Chicago chain restaurant - named Portillo's. People really love it in Chicago. They go for the Italian beef and stay for the crinkle fries and famous “cake shakes” (they put a whole cake slice into a milkshake). There is one right in the heart of the city, but you can find them all around. An easy stop for lunch.

4. Find the Perfect Cheese Curds

What are cheese curds?

The least appetizing way to describe it is curdled (hence, curds) milk that has been fried. A slightly more appetizing way to describe it is basically just fried cheese tots!

Tell me more…

Need I say more? Fried cheese people. It is heaven. Wisconsin is known for their cheeses, and Chicago is basically a stone’s throw away. You can find these at plenty of casual establishments and bars. You won't be disappointed---it's as amazing as it sounds.

5. Snack on Some Chicago Style Popcorn

What is different about Chicago style popcorn?

You take caramel dipped popcorn, you take cheddar cheese flavored popcorn, and you mix them into one bowl. Yup.

Tell me more…

Okay, I get the hesitation. Caramel and cheddar? Why? Even I look at it and wonder why. But trust me. TRUST ME. Every time I grab one kernel of each flavor at once, I am overwhelmed by both deliciousness and confusion. It truly is a weirdly perfect combo. (plus, didn’t I mention how close we are to Wisconsin cheese? Even the cheddar popcorn by itself is going to be some of the best you’ve ever had.)

Take a stop by the famous Garrett Popcorn Shop!

6. Explore Chicago's History of Delicious Fish Fry

Chicago has a deep history of segregation and discrimination, especially in regards to neighborhoods and real estate. It is history worth learning about and from. Because of this, different foods have become stapes of the Chicago region, hailing from different areas of the United States and the world. One classic Chicago dish attributed to this is fish fry.

My words aren’t as poignant as Audarshia Townsend’s, who writes about this on Anthony Bourdain's “Parts Unknown” site:

I also highly suggest watching the whole Chicago episode of Parts Unknown in Season 7 called, “Slice of Life.” It sums up Chicago beautifully and explores this deep history more.

7. Fill Up with a Classic Midwestern Breakfast

(Walker Brothers Pancake House & Ann Sather)

Another staple in our family is Walker Brothers Pancake House. My parents made a deal with me in 5th grade that if I ever got 100% on my Friday spelling tests, they would take me to the Pancake House on Saturday morning. I am not kidding you, I got 100% every Friday for the whole year. At one point my parents tried to renegotiate because going to brunch every Saturday is not cheap. What can I say, I am motivated by breakfast food. Their pancakes are amazing.

Another famous breakfast spot is Ann Sathers. It is a delicious and adorable Swedish diner that has been around forever. They are especially famous for their cinnamon rolls (don't miss these!).

8. Splurge on Some Michelin & Bib Gourmand Restaurants

Chicago is FULL of delicious and critically acclaimed restaurants. Although it is always fun to go to the local spots, definitely take advantage of the new and upcoming fine dining as well. Chicago has been awarded 25 one- two- and three-star restaurants in 2020, and 54 Bib Gourmand recommendations.

Alinea is particularly famous, and if you want a reservation, you need to get on that yesterday. Some of my favorites are by Chef Stephanie Izard, who founded Girl & the Goat, Little Goat, Duck Duck Goat, Cabra, and Tiny Goat. They’re all amazing Chicago restaurants with different specialties and mixes of flavors.

In addition, I feel like it's required that I mention Au Cheval, known for being the “best burger in the United States” at one point. People wait for hours (and hours and hours) to have a taste of an Au Cheval burger. If you have a whole morning and love burgers, give this place a try.

A little tip: there are a couple of "Small Cheval" restaurants around town that are much easier to grab a burger at!

9. Tour Some Chicago Breweries

Chicago is FULL of amazing breweries, located all over the city. As of 2018, it has more breweries than any other city in the US actually, with 167. Although the numbers have changed since, it is definitely worth exploring some spots while you're in town if you're a beer lover. Some favorites are Half Acre, Revolution, Dovetail, and Begyle.

Expect a separate post about breweries later!

10. Relax into the Night at a Famous Jazz Bar

Chicago Jazz is famous for a reason. Although the longtime jazz bars are slowly disappearing, it is worth visiting one while you still can. This is a fun, Chicagoan way to drink and enjoy live music into the night. The Green Mill is particularly well-known, but there are quite a few fun ones downtown to enjoy -- especially if you're a late-night cocktail lover.

For Fun: Malört

Had to be mentioned: Malört. Every Chicagoan is chuckling right now. Malört is kind of a baptism by fire into the Midwest. It is a Chicago liquor introduced in the 30’s that has basically become a novelty drink. For example, many Chicagoans make out-of-towners take Malört shots to welcome them. Many say you aren’t a real Chicagoan until you’ve tried it. I actually know some Chicagoans (life-long Chicagoans) that drink it non-ironically. I must warn you, it's terrible. But it's just about as local as you can get.

Any other suggestions? Let us know!

Written by Emi Lungmus

Photos by Emi Lungmus

Edited by Anna McCarthy


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