Chicago Foodie Bucket List: 21 Dishes To Try Before You Die

From the North Side to the South Side, Chicago has irresistible food on every corner, so it’s the perfect spot to tackle a Chicago food bucket list. Home to the deep dish pizza, overflowing sandwiches and Chicago-style hot dogs, this is a city with a serious culinary vibe.

As well as deliciously dirty street food, Chicago also has more than its fair share of talented chefs and innovative restaurants. Looking to eat your way around the city? These are the top 21 dishes you have to try at least once…

Chicago Foodie Bucket List: 21 Dishes To Try Before You Die, How do these rankings work?

1. T-Bone Steak – Gene & Georgetti’s

Gene & Georgetti’s has been serving steaks and Italian specialties since 1941 and are a top pick for a feast in Chicago. Their 42.oz Signature Broiled T-Bone for two is an absolute classic: juicy and tender with a choice of drool-inducing sides such as garlic mashed potatoes and creamy spinach.

2. The Superdawg – Superdawg

Superdawg is a drive-in Chicago institution. Not a wiener, not a frankfurter, not a red hot, but their tried-and-test pure beef hot dog that’s super juicy and comes in a poppy seed bun. Go wild with the toppings and don’t forget to add the pickled tomato.

3. Bing Bread – Parachute

Potato bread is transformed into the tastiest dish in town at Parachute, fun Korean American restaurant. Their famous Bing Bread has scallions, cheddar and Broadbent’s Kentucky bacon baked into the dough, brushed with sesame oil, fried and finished in the oven.

4. Fat Rice ‘Arroz Gordo’ – Fat Rice

Fat Rice is a funky bar and restaurant that celebrates the unique cuisines of Portuguese speaking Luso-Asian provinces, with an emphasis on Macau, China. With lots of tasty bites on the menu, it’s their namesake dish you really need.

The Arroz Gordo is similar to a paella, with curried chicken thigh, char siu pork, linguiça sausage, chilli prawns and clams.

5. Rainbow Cone – The Original Rainbow Cone

You haven’t lived if you’ve not had one of these cones from this iconic ice cream store. The Original Rainbow Cone is made up of five distinct flavors: chocolate, strawberry, Palmer House (New York vanilla with cherries and walnuts), pistachio and orange sherbet.

6. Sushi Burrito – En Hakkore 2.0

This hip food joint serves up colorful sushi burritos, sushi tacos, poke bowls, and other tasty dishes. Get the Crunch + Fire sushi burrito: Shrimp tempura, spicy tuna, cream cheese, jalapeno, mashed sweet potato, flakes, cucumber, guacamole, lettuce, avocado, soy glazed sauce, and spicy mayo sauce.

7. Tasting Menu – Alinea

If you can work some sort of magic to snag a table at this eternally sold-out 3-star Michelin hotspot, you’ll be in heaven. Alinea has a single, seasonally driven tasting menu of between 18 and 22 courses. Food is presented like works of art, with ingredients used in provocative and imaginative ways.

8. Italian Beef Sandwich – Portillo’s

For Chicagoans, there’s only one sandwich to beat all others, and it’s gotta be an Italian beef. Head to Portillo’s for the classic hero, which you can get made exactly to your liking with gravy and four different types of cheese toppings.

9. The Wolf Burger – Little Bad Wolf

You simply have to try the Wolf Burger at this trendy restaurant. With three beef patties, creamy melted American cheese, onion straws, house-made pickles, mayo and a fried egg, it’s an absolute beast.

10. Deep Dish Pizza -Lou Malnati’s Pizzeria 

They’ve been in business since 1971 and are part of the legend of Chicago pizza scene at this stage. The place to come if you want to try a truly authentic deep dish style pizza.

Any business that has been going this long is going to be good at what they do and you only have to look at the lines in their restaurants to see locals agree. Sublime.

11. Chicago Mix Popcorn – Garrett Popcorn

The incredible mix of cheddar cheese and caramel popcorn might no longer be called the ‘Chicago Mix’ (it’s officially the Garrett Popcorn Mix) but that doesn’t stop everyone from saying the original name. The sweet and savoury bites are a must-try.

12. Jibarito – Papa’s Cache Sabroso

Papa’s Cache is a chilled out family owned-and-operated restaurant that serves authentic Puerto Rican food. Their most popular – and tastiest – dish is their famed Jibarito. Either chicken or grilled beef is sandwiched between razor-thin fried plantains that are crispy and delicious.

13. BBQ – Smoque BBQ

Smoque (smōk) BBQ cooks up ribs, pulled pork and brisket good enough to hold pride of place anywhere in Kansas City, Memphis, North Carolina and Austin. They smoke smoke their meat over oak and sweet applewood and the end result is pure perfection. It’s also BYOB, so bring a cold one or two.

14. Jackhammer – Andy’s Frozen Custard

Andy’s Frozen Custard is a must-try Midwest staple, and no visit to Chicago is complete without one. Creamier than regular ice cream, frozen custard contains more butterfat and there’s plenty of flavours to try here. The Jackhammer is the best: choose your flavour and they’ll fill the middle of it with a topping of your choice.

15. Shrimp de Jonghe – Hugo’s Frog Bar & Fish House

A top spot in the city for spot for fresh oysters, crudos, frog legs, lobster and fish, but this classic dish is a must. Shrimp De Jonghe is a classic Chicago dish of fresh shrimp underneath garlicky breadcrumbs. It’s been around since 1923 and never fails on flavour.

16. Caviar – Oriole

Oriole is a fine dining restaurant in the West Loop neighborhood with two Michelin stars that does a fantastic 14-course tasting menu. Each dish is outstanding but the very first one – the caviar – is a real star. It comes with white asparagus and butterscotch and is the perfect way to to kick start a great meal.

17. Chicken Wings – Great Sea Chinese Restaurant 

Great Sea Restaurant offers the best spicy chicken wings in the entire Chicago area. These are wings that pack a serious punch and are perfectly prepped so that you can easily get at the proper meaty bits. Better have a cold beer ready for that heat though!

18. Chorizo Medjool Dates – Avec

These chorizo-stuffed-bacon-wrapped dates have a cult following and are reason alone to go to this Midwestern/Mediterranean restaurant. The juicy Medjool dates release incredible flavour with the salty bacon and chorizo, and the whole thing comes in a piquillo pepper sauce.

19.  Pizza Puff – Albano’s Pizzeria

Is it good for you? No. But does it taste good? HELL YES. The legendary Pizza Puff at Albano’s is basically a fried calzone, but you can also get it baked. Choose your fillings and bring an appetite for this delicious beast. The crust is buttery and flakey and the mozzarella and homemade marinara sauce comes oozing out.

20. Crab and Waffle Fries – Giant

Giant are masters of simple, tasty food that’s been given a chef upgrade with pure skill in every dish. The Jonah crab salad is served alongside chunky and crispy waffle fries made of piped mashed potatoes that are fried in butter. So. Goddamn. Tasty.

21. Tasting Menu – Smyth

There’s three tasting menus to choose from at this farm-to-table fine dining restaurant. They have an exclusive partnership with a 20-acre farm an hour south of Chicago, which provides most of the produce, herbs and flowers, as well as inspiration for food and drinks.

Dishes include Caramelized Halibut With Blood Sausage & Toasted Crab or Beef Fat Brioche Doughnuts.