14 Classic Chicago Foods That Prove The Windy City Knows Comfort Food Best
Chicago doesn’t just do comfort food. It perfects it, layers it, deep-fries it, and serves it with a side of attitude.
Whether it’s a cheesy slice that weighs more than your phone or a sandwich that could double as a pillow, the Windy City takes pride in bold flavors and big portions.
Forget trendy plates and microgreens. This is food that hugs you back, sticks to your ribs, and tells you you’re home, even if you’re not.
1. Chicago Deep-Dish Pizza
Forget everything you know about pizza. This glorious pie-like creation features a buttery crust that climbs up the sides of a deep pan, creating a fortress for rivers of chunky tomato sauce, mountains of cheese, and hearty toppings.
Born in 1943 at Pizzeria Uno, this Chicago icon requires a knife and fork and probably a nap afterward.
The upside-down construction (cheese first, sauce on top) prevents burning during the long bake time.
2. Chicago-Style Hot Dog
Ask for ketchup on this bad boy and you’ll immediately reveal yourself as an out-of-towner.
The Chicago dog is an all-beef frankfurter nestled in a poppy seed bun, then ‘dragged through the garden’ with yellow mustard, neon-green relish, onions, tomato wedges, pickle spear, sport peppers, and celery salt.
This colorful masterpiece emerged during the Great Depression when vendors added extra toppings to create a more filling meal.
3. Italian Beef Sandwich
Heaven between bread! Thinly sliced roast beef soaked in its own savory juices gets piled high on a sturdy Italian roll that somehow maintains its integrity despite being gloriously wet.
Locals order it ‘dipped’ (the whole sandwich dunked in jus), ‘sweet’ (with sautéed bell peppers), or ‘hot’ (with giardiniera).
The sandwich was created by Italian immigrants during the 1930s as a way to stretch tough cuts of beef into delicious, economical meals.
4. The Combo (Italian Beef & Sausage)
Why choose between two iconic Chicago meats when you can have both?
The Combo marries an Italian beef sandwich with a juicy Italian sausage, creating a protein powerhouse that challenges even the most ambitious appetites.
Some places put the sausage on top of the beef; others slice it in half lengthwise. Either way, you’re in for a messy, magnificent experience that requires at least three napkins and zero shame.
5. Chicago Tavern-Cut Thin Crust Pizza
While deep-dish gets all the glory, many Chicagoans secretly prefer this cracker-thin, party-cut pizza.
The ultra-crisp crust snaps when you bite it, supporting a thin layer of tangy sauce and a generous blanket of cheese that extends right to the edge.
Cut into squares instead of triangles (sacrilege to New Yorkers!), tavern-style creates the beloved ‘corner pieces’ with extra-crunchy edges.
This style actually predates deep-dish in Chicago but doesn’t get nearly the same tourist attention.
6. Maxwell Street Polish
Sausage royalty! This street food legend features a kielbasa-type sausage that’s split down the middle, grilled until charred, then topped with mountains of caramelized onions and yellow mustard on a sturdy roll.
Sport peppers add heat for the brave. Named after Maxwell Street Market where it was popularized, this handheld delight gained fame at Jim’s Original and Express Grill, whose owners still argue over who created it first.
7. Jibarito Sandwich
Who needs bread when you have plantains? This Puerto Rican-Chicago hybrid uses crispy fried green plantains as the ‘bun’ for a filling of savory steak, lettuce, tomato, cheese, and garlicky mayo.
Created in the 1990s at Borinquen Restaurant in Humboldt Park, the jibarito (pronounced hee-bah-REE-to) showcases Chicago’s innovative immigrant food culture.
The contrast between the crunchy plantains and juicy fillings creates a textural masterpiece unlike anything else.
8. Chicken Vesuvio
Born in Chicago’s Italian restaurants, this stunning one-pan wonder combines bone-in chicken, crispy potato wedges, and whole garlic cloves roasted until golden, then doused with white wine, herbs, and lemon juice.
Green peas often make a colorful cameo. Unlike many Chicago classics, you won’t find this dish on street corners. It’s a sit-down restaurant specialty that somehow never gained national fame despite its incredible flavor profile.
9. Shrimp de Jonghe
Fancy meets comfort in this vintage Chicago creation. Plump shrimp swim in a luxurious bath of garlic butter, topped with seasoned breadcrumbs and baked until golden and bubbly.
Invented at DeJonghe’s Hotel and Restaurant in the early 1900s, this dish survived Prohibition (which shuttered the original restaurant) to become a mainstay on old-school Chicago menus.
It’s typically served in a shallow gratin dish with crusty bread for soaking up that liquid gold.
10. Chicago-Style Giardiniera
Chicago’s favorite condiment packs a punch! This spicy mix of oil-marinated vegetables, typically hot peppers, celery, cauliflower, carrots, and olives, adds crunch and heat to sandwiches, pizzas, eggs, and anything else needing a flavor boost.
Unlike Italian versions, Chicago giardiniera uses oil instead of vinegar as the primary preserving liquid.
Available in ‘hot’ or ‘mild’ varieties, locals debate which brand reigns supreme with the fervor usually reserved for sports teams.
11. Chicago Mix Caramel & Cheese Popcorn
Sweet meets savory in this addictive combination of caramel-coated and cheese-flavored popcorn, eaten together by the handful for a flavor explosion that shouldn’t work but absolutely does.
Garrett Popcorn Shops made this mix famous, though they had to rename it ‘Garrett Mix’ after trademark issues.
The contrast between sticky-sweet caramel corn and bright orange cheesy kernels creates a snacking experience that’s greater than the sum of its parts.
12. Original Rainbow Cone
Summer in Chicago isn’t complete without this colorful creation from the South Side ice cream shop of the same name.
Five distinct flavors are in there. Chocolate, strawberry, Palmer House (vanilla with cherries and walnuts), pistachio, and orange sherbet are sliced, not scooped, into a precise stack on a cone.
Operating since 1926, this dessert is a masterclass in flavor combination, with each taste complementing the next as you work your way down.
13. Chocolate Cake Shake
Portillo’s broke the dessert matrix with this outrageous concoction which is an entire slice of rich chocolate cake blended into a chocolate milkshake.
The result? A thick, straw-defying treat with cake pieces still visible throughout. First-timers often laugh at the concept until they taste it. Then they’re converted for life.
The shake manages to maintain the distinct texture of both cake and ice cream, creating something entirely new that has spawned countless copycat attempts.
14. South Side Rib Tips & Hot Links
Chicago’s barbecue identity centers on this unique combo plate found in smokehouses across the South Side.
Rib tips, the cartilage-rich end pieces trimmed from spare ribs are slow-smoked until tender, then chopped into bite-sized morsels.
They’re served alongside spicy hot link sausages, all drenched in tangy sauce and piled atop white bread with french fries.
This style emerged from African American communities and remains one of the city’s most underrated culinary treasures.