Food & Drink

Chicago's 11 Most Ridiculous Eating Challenges

Published On 02/03/2015 Published On 02/03/2015
fatso's last stand

Chicago You know what they say about eating in Chicago: "When you love something, set it free... or do it competitively for a free T-shirt... or maybe a gift card? Or... both???" For those of you interested in the latter, we've compiled this list of the 11 best eating challenges in town, complete with all the deets on what you have to take down -- and what you win if you do. More Stuff You Will Like

rudy's bar & grille

Challenger Burger

Rudy's Bar & Grille (address and info)   Loop Time Limit: 30 minutes
Prize: A comped meal, a T-shirt, a $100 gift card, and you get to sign the wall of champions
The Challenger Burger at Rudy’s Bar & Grille is a burger inasmuch as the slimy banker your mother married is your new father. In reality, there are hamburger patties in there somewhere, but you’ll have to find them by digging through a 5.5lb skillet that includes eggs, bacon, cheese, and hash browns. Continue Reading

paddy long's

Bacon Bomb

Paddy Long's (address and info)   Lakeview Time Limit: 45 minutes
Prize: A T-shirt, a spot on the wall of fame, and a comped meal
Yeah, yeah, everyone loves bacon. But this is a whole different level: Paddy Long’s Bacon Bomb is a 5lb loaf of ground sausage, pork, and beef that surrounds a pepper-bacon center and has a sugar-bacon-weave exterior, all served with a huge side of fries.

fatso's last stand

Po'Boy Challenge + Jumbo Fatso Challenge

Fatso's Last Stand (address and info)   Ukrainian Village Time Limit: 45 minutes
Prize: A T-shirt, your name on a plaque, a comped meal, and a $50 gift card to Lockdown Bar & Grill
The Po’Boy Challenge at Fatso’s Last Stand features an absurd seven-pound sandwich that’s made with 2lbs of fried jumbo shrimp, coleslaw, pickles, lettuce, tomatoes, special sauce, cheddar cheese sauce, and shoestring fries. You’ll have to finish off a pound of fries and a 32oz soda as well. If you’re not feeling up to the po’boy just yet, there’s also a Jumbo Fatso challenge that consists of a 5lb burger with a half pound of fries (that's it pictured above).

wiener and still champion

Triple Undisputed 911 Burger

Wiener and Still Champion (address and info)   Evanston Time Limit: None
Prize: Heartburn, alongside a sense of satisfaction
When an eating challenge has “911” in its name, you know it will definitely kill you... oh, uh, or like, um, be lots of fun? Or something? Either way, this towering creation features 3lbs of beef, nine patties, and eleven slices of cheese.


The Slinger

Diner Grill (address and info)   Lakeview Time Limit: None
Prize: A certificate!
The Slinger at Diner Grill isn’t really much of challenge to finish (it's a car-wreck of hash browns, eggs, chili, onions, cheese, and hamburger patties), but look at the picture of it above and tell us you don't think that would be hard to eat? Yup.  

Ultimate Eating Challenge

The Fifty/50 (address and info)   Wicker Park Time Limit: 50 minutes
Prize: A T-shirt, a photo on the wall of fame, and a comped meal
For those who like a little bit of variety with their gastrointestinal complications, the Ultimate Eating Challenge at The Fifty/50 offers a variety of eats in one epic challenge. The whole shebang includes (take a deep breath) 30 Buffalo wings, five bacon strips, five onion rings, one side of mac & cheese, a half rack of ribs, one burger slider, one turkey burger slider, one pulled pork slider, one duck breast slider, one grilled cheese slider, one crab cake slider, one PB&J slider, and 50oz of beer (exhale).


Lucky's Challenge

Lucky's Sandwich Co. (address and info)   Wrigleyville Time Limit: 1 hour
Prize: T-shirt, a photo on the wall of fame, and all three sandwiches comped
Popularized by Man v. Food, this eating challenge offers the opportunity to live out an episode of You v. Man v. Food. Simply choose three of the qualifying sandwiches -- all of which are stuffed with fries.

rocks lakeview

Rockstar Challenge

ROCKS Lakeview (address and info)   Lakeview Time Limit: 30 minutes
Prize: A T-shirt, recognition in the hall of fame, and a comped meal
The Rockstar Burger at Rocks Lakeview looks more like the Leaning Tower of Pisa, if the Leaning Tower of Pisa were made of cheeseburger. It features four Angus beef patties topped with eight slices of bacon, giardiniera, cheese, onion strings, lettuce, and pickles, all on a pretzel bun served with a pound of fries. The whole meal weighs 4lbs.

timothy o'toole's

Big Timmy Challenge

Timothy O'Toole's (address and info)   Near North Side Time Limit: None
Prize: An O'Toole's T-shirt
The fact that this challenge is actually doable for mere mortals also makes it great for, you know, actually enjoying your meal. This tasty-looking burger comes with two half-pound patties topped with cheddar, mozzarella, jack, Swiss, onion straws, bacon, barbecue sauce, lettuce, tomato, onions, and fries.

jake melnick's corner tap

XXX Hot Wings Challenge

Jake Melnick's Corner Tap (address and info)   River North Time Limit: None
Prize: Your photo on the Wall of Flame
The cooks here do not mess around. Challengers will have to sign a waiver before proceeding, and the wings are made with the Trinidad Scorpion pepper... which sounds really freaking hot because, again, it’s called the TRINIDAD SCORPION PEPPER, in case you missed that. Finish the order without ringing the bell for a "cooling plate," and you’ll get your photo on the Wall of Flame. Sign up here for our daily Chicago email and be the first to get all the food/drink/fun in town. Raf is a long-tenured Baratheon loyalist and Point Break apologist. You can check out his weird-smelling blog Alley Connoisseur, and follow him at @RafFoSho.

Previous Venue Next Venue Venue Description
1. Rudy's Bar and Grille 69 E Madison, Chicago, IL 60603

A memorabilia-packed burger joint from the pizza-slinging family behind nearby Pizano's, Rudy's offers 3/4lb prime patties like the cheddar/bacon/fried egg Breakfast Burger and much more.

Previous Venue Next Venue Venue Description
2. Paddy Long's 1028 W Diversey, Chicago, IL 60614 (Lincoln Park)

Paddy Long's has acquired numerous varieties of Bourbon County Stout for your barrel-aged beer drinking pleasure (which has led to your pleasing barrel shape), tapping this year and last year's original vintages along with variants like vanilla, coffee, and the recently released cherry rye.

Previous Venue Next Venue Venue Description
3. Fatso's Last Stand 2258 W Chicago Ave, Chicago, IL 60622 (Ukrainian Village)

This no frills, Ukrainian Village eatery pretty much has the perfect name, with a menu chock-full of items like fresh-cut fries, char dogs, and burgers. One of the staples here is the Double Fatso with cheese -- two perfectly grilled beef patties flanked by slices of American cheese, onion, and secret sauce -- a burger that can give In-N-Out a run for its money.

Previous Venue Next Venue Venue Description
4. Wiener & Still Champion 802 Dempster St, Evanston, IL 60202 (Evanston)

More than just a hilarious name, W&SC serves award-winning hot dogs, as well as other sandwiches, burgers, and American grub.

Previous Venue Next Venue Venue Description
5. Diner Grill 1635 W Irving Park Rd, Chicago, IL 60613-2526 (Lakeview)

Slinging diner-style fare in Lakeview, The Diner Grill features 'merican grub staples like burgers and breakfast.

Previous Venue Next Venue Venue Description
6. The Fifty/50 2047 W Division St, Chicago, IL 60622 (Wicker Park)

The 50's a tri-level sports temple serving gluttonous fare like in-house smoked meats (ribs, pulled pork, wings), mac 'n' cheese toppable with everything from chicken to chili, and the "Double-Secret Probation"-esque "Triple Secret:" a tri-meat fatburger with a classified recipe.

Previous Venue Next Venue Venue Description
7. Lucky's Sandwich Co. 3472 N Clark St, Chicago, IL 60657 (Wicker Park)

Lucky's serves up Pittsburgh-style sandos that'll fill ya up, especially if you get a side of their deep-fried hunks of Provolone. Attempt the Lucky’s Challenge, because why opt for just one Pittsburgh-style hulk sandwich with fries and coleslaw in it when you could have THREE stacked with different kinds of deli meats? Devour all overstuffed sandwiches within an hour, and all of 'em are on the house and your pretty mug will live on wall of fame style, which is just as cool as doing it for Man v. Food, right?

Previous Venue Next Venue Venue Description
8. ROCKS Lakeview 3463 N Broadway St, Chicago, IL 60657 (Lakeview)

Get some great beer and ROCK-solid bar food (we're so sorry), or cut the nonsense and go straight for the Rockstar Challenge: four Angus beef patties topped with eight slices of bacon, giardiniera, cheese, onion strings, lettuce, and pickles, all on a pretzel bun served with a pound of fries.

Previous Venue Next Venue Venue Description
9. Timothy O'Toole's 622 N Fairbanks Ct, Chicago, IL 60611 (Near North Side)

TOT has everything you could want in a dive bar and more: billiards, classic bar food, 48 beers on tap and over 70 HD televisions. The menu offers wings and burger staples as well as healthy options and a children’s menu. Stop in on the weekend for brunch, featuring a Build Your Own Mimosa and Bloody Mary drink bar. This neighborhood pub hosts events such as trivia, karaoke, and comedy nights.

Previous Venue Next Venue Venue Description
10. Jake Melnick's Corner Tap 41 E Superior St, Chicago, IL 60611 (River North)

Jake Melnick's Corner Tap is a beer bar in River North, Chicago that's serving up some killer hot wings and other bar foods.