Chicago: From Deep Dish to Donuts: The Ultimate Chicago Food Tour

Chicago is a city that takes its food as seriously as its sports, so get ready to dive into a culinary adventure! From deep-dish pizza that could double as a skyscraper to hot dogs that have more toppings than you can count, Chicago’s food scene is as iconic as its skyline. Whether you're a local or a first-time visitor, these are the must-try dishes that will have your taste buds cheering for the home team!

Rainbow Cone — The Original Rainbow Cone

​At The Original Rainbow Cone, a Chicago staple since 1926, the Rainbow Cone is a five-flavor extravaganza that turns every ice cream lover's dream into reality. This towering treat slices together chocolate, strawberry, Palmer House (a cherry and walnut blend), pistachio, and orange sherbet, creating a vibrant spectrum of flavors in every bite. Served in a cone or cup, it's a visual and gustatory delight that's been bringing smiles to faces for nearly a century.

Jibarito — Borinquen Lounge

At Borinquen Lounge in Chicago, the jibarito is more than just a sandwich—it's a culinary legend. Invented by Juan "Peter" Figueroa in 1996 at the original Borinquen Restaurant in Humboldt Park, this innovative creation replaces traditional bread with crispy, twice-fried plantains, embracing Puerto Rican flavors in a uniquely Chicagoan way . Layered with tender steak, garlicky mayo, melted cheese, lettuce, and tomato, each bite delivers a harmonious blend of savory goodness and satisfying crunch.

Italian Beef — Al's #1 Italian Beef

At Al’s #1 Italian Beef, you're not just grabbing a sandwich—you’re biting into a messy, meaty piece of Chicago history. This legendary joint has been slinging its signature Italian beef since 1938, and it’s easy to see why it’s stood the test of time. Thinly sliced beef, slow-roasted and soaked in savory jus, is piled high on a fluffy Italian roll and optionally topped with sweet peppers or spicy giardiniera. Pro tip: get it "dipped" so the whole sandwich takes a glorious dunk in that rich gravy. It’s juicy, it’s drippy, and it’s absolutely iconic—just don’t forget the napkins!

Pepperoni Deep Dish — Pequod's Pizzeria

At Pequod’s Pizzeria in Chicago, the pepperoni deep dish isn't just a meal—it's a molten, caramelized masterpiece. This legendary pie boasts a thick, buttery crust that's baked to perfection, with a generous layer of pepperoni nestled beneath a rich, tangy tomato sauce and gooey mozzarella. What sets it apart? That signature caramelized cheese crust, achieved by pressing cheese between the crust and the cast-iron pan, creating a crispy, flavorful edge that's pure bliss.

Lollipop Chicken Wings — Great Sea Restaurant

At Great Sea Restaurant in Chicago's Albany Park, the Lollipop Chicken Wings are a must-try culinary delight. These drumettes are expertly trimmed to resemble lollipops, then fried to a perfect crisp and coated in a sticky, sweet-and-spicy sauce that keeps patrons coming back for more. Whether you opt for the regular or extra spicy version, each bite offers a harmonious blend of flavors that has earned these wings a spot among Chicago's best .

Superkhana International — Butter Chicken Calzone

At Superkhana International in Chicago's Logan Square, the Butter Chicken Calzone is a delightful fusion of Indian and Italian cuisines. This inventive dish features tender butter chicken wrapped in chewy naan dough, combined with mozzarella and Amul cheese, then baked and finished with ghee and Maldon salt for a luxurious touch.

Chicago Dog — Fixin Franks 

At Fixin’ Franks, nestled inside various Chicago-area Home Depots, the classic Chicago Dog gets a delightful twist that's both unexpected and unforgettable. While you're shopping for your next DIY project, this unassuming stand offers a culinary detour with their standout offering: the Wagyu beef Chicago Dog. Sourced from Makowski’s Real Sausage Co., these premium dogs are grilled to perfection and "dragged through the garden" with all the traditional fixings—mustard, onions, relish, tomato slices, a pickle spear, sport peppers, and a dash of celery salt—strictly no ketchup, of course.

Atomic Cake — Weber's Bakery

At Weber's Bakery, the Atomic Cake, locally known as the Banana Split Torte, is a towering testament to Chicago's rich baking heritage. Crafted from layers of banana, yellow, and chocolate cakes, it's generously filled with Bavarian cream, fresh bananas, glazed strawberries, and chocolate fudge, all enveloped in a fluffy whipped cream exterior. This indulgent creation, a staple since the 1950s, is exclusive to the city's South Side, reflecting the area's unique culinary traditions.

Chicken Vesuvio — Gene & Georgetti

The famous Chicken Vesuvio was created by Chef Frank Merletti in the late 1940′s, and has been served ever since. Their dish is their signature chicken on the bone with crispy potatoes cooked in olive oil and garlic, finished with white wine. It’s a classic and iconic Chicago classic that you must try the next time you are in town. 

Saganaki — Greek Islands 

At Greek Islands in Chicago's Greektown, the saganaki isn't just an appetizer—it's a fiery spectacle that ignites the dining experience. Picture this: a sizzling slab of kefalotyri cheese arrives at your table, is flambéed with brandy, and set ablaze as the staff exclaims "Opa!" The flames dance briefly before a squeeze of lemon extinguishes them, leaving behind a crispy, gooey delight that's as flavorful as it is entertaining. This tableside tradition, though rooted in Chicago rather than Greece, has become a beloved ritual, making saganaki at Greek Islands a must-try for both locals and visitors seeking a taste of culinary theater.

Before you roll yourself home or into a deep-dish-induced nap, remember: eating your way through Chicago is basically a sport—and you've just gone pro. From flaming cheese and beefy sandwiches to rainbow cones and butter chicken calzones, the Windy City brings the flavor, the flair, and the food coma. Head over to hellozeal.ai and book any of these restaurants in seconds!