Chicago’s food scene packs a punch with bold flavors and generous portions. When it comes to over-the-top eats, some local spots are dishing out belly-busting challenges that blur the line between meal and mayhem. These aren’t just dishes, they’re dares, built to stretch stomachs, test limits, and earn serious bragging rights (or a legendary food coma). In a city known for going big, these outrageous bites don’t hold back.

Chow challenges

Fontano’s Subs & Pizzeria on Michigan

The Three-Foot Meatball Challenge dares solo eaters to tackle 16 meatballs, 16 slices of mozzarella, and a whole loaf of French bread in under an hour because the T-shirt and gift card won’t win themselves. 

ROCK Star Burger Challenge at ROCKS– Lakeview

The challenge is simple: devour a towering eight-pound burger loaded with toppings, plus fries and a drink, in under 30 minutes to earn a spot on the ROCKS wall of fame. 

Jake Melnick’s XXXX Hot Wings Challenge – River North

Brave diners attempt to conquer six fiery wings coated in a secret ghost pepper sauce (a blend of Carolina Reaper, Trinidad Scorpion, Ghost Pepper, and Habanero), without the aid of ranch, milk, or mercy. 

Timothy O’Toole’s Pub Big Timmy Challenge – Chicago

Contenders dare to finish a triple-decker burger stacked with nine patties, heaps of cheese (cheddar, jalapeno jack, mozzarella, and Swiss), and a pound of fries in under 30 minutes. 

Strings Ramen Monster Hell Ramen Challenge – Chinatown, Lakeview, and Hyde Park

When a challenge comes with a warning label, it’s not about finishing, it’s about surviving. The XXXX Challenge is a bowl of insanely spicy broth loaded with ghost peppers and chili oil. Finish it fast and earn eternal bragging rights and the hottest seat in the place. 

The Mega Cheesie’s Challenge at Cheesie’s Pub & Grub – Lakeview, Garfield Ridge, Wicker Park

Diners dare to demolish a 16-inch, eight-pound mélange of five loaded grilled cheese sandwiches and one pound of fries in 30 minutes. (You can earn ten extra minutes for every friend you bring with you to cheer you on!) The restaurant requires 48-hour notice for the challenge.

Gargantuan grub

Dat Donut – Chatham, Lakeview

The “Big Dat” is a colossal, plate-sized glazed donut. They proudly claim it’s as big as your head, and yes, they mean it. 

Nonna’s Goodlife Pizza for all – LaGrange, Crestwood, Oak Lawn

Nonna’s in Chicago serves up the “World’s Largest Slice” of pizza. It is so big it barely fits on a tray. Their stadium-sized pizza is a massive 468 square inches of party pie built to feed eight to ten people – or an entire team.

 Cesar’s Killer Margaritas & Mexican Restaurant – Lakeview

The Super Mega-Rita isn’t just a drink; it’s a pool party served in a goblet big enough to swim in and available in more flavors than you’ve got good decisions.

Mr. Chilaquil – Archer Heights

The giant concha is a sugar-loaded showstopper, perfectly matched with their oversized Cafecito, a duo so indulgent it should come with a warning (or a nap).

 Pizzeria Portofino – River North

The Portofino Purse is a playful twist on cocktail hour. A cocktail or spritz flavor from their drink menu is served in a glass handbag big enough to serve two to four guests.

 Martinez Mexican Bar & Grill – Bridgeport

Their Big Baby Burrito is a seven-pound food coma waiting to happen.

Tanuki Sushi & Grill – Lakeview

The Sushizza Box is where sushi shows up dressed like pizza. Choose eight rolls from over 30 choices served in a pizza box, for pick-up or delivery only.

 WOW Pizza – Edgewater, Lakeview

Size matters, especially when it’s 30 inches of cheesy glory. This pizza is more of a team sport than dinner.