Chicago Traveler Blog

Chicago Traveler Blog

Chicago Food Challenges Every Eater Should Try

7/23/12 | by

Chicago likes to do things BIG. Big names in sports, extremely tall buildings, and the deepest of pizzas. But the pizzas aren't the only thing bigger (and more gut wrenching) in Chicago than in many other cities, because Chicago is known to have some of the hardest food challenges to beat as well!

This city loves to make eaters suffer a little for their free meal and spot in their Hall of Fame. Here are a few of our favorite food challenges in Chicago, because we love feeling miserable, satisfied, glorified and on the verge of barfing our brains out, all at the most flattering same time.

Pizza Challenges - Because what would the city known for their pizza be without them?
30's Pizza Factory: Get a 30 inch pizza to split between 3 people in an hour or less and get your picture on the Wall of Fame and your next pizza is free. So yeah, your reward for finishing a ton of pizza is more pizza... But it's better than a lousy t-shirt, right?

Sandwich Challenge
Lucky's Sandwich Company
: Possibly the most famous food challenge in Chicago, at Lucky's you can personalize the sandwich to your liking. The sandwiches in their contest menu are roast beef, smoked turkey, pastrami, Cajun chicken and more, and you choose 3, which you have to eat in an hour or less. Complete your mission and get one sandwich free, a Lucky's T-shirt and your photo on their Wall of Fame. You'll be right up with Adam Richman, who completed the challenge on season one of "Man V. Food." As an added bonus, if you finish in less than 30 minutes, you get all 3 sandwiches free!

Brand's BBQ Challenge
While Chicago isn't especially known for their BBQ, Brand's BBQ Market is a Logan Square gem, and their food challenge is delicious to the very end - as painful as it may be. Try downing 18 inches of French bread, loaded with delicious burnt ends, mac and cheese and smoked gouda. Also included in the meal are hand cut fries and slaw, that you have to finish in less than an hour. Complete the challenge, and you get the meal (that usually costs $29.95) for free.

Burger Challenge
Timothy O'Toole's: The Big Timmy Challenge consists of two 1/2 lbs burger patties, 4 cheeses, BLT, onion straws and red onions, as well as fries and onion rings on the side. In other words, don't bring a girl here for this on the first date and expect a first kiss. But if you do, and she does the challenge with you, you might want to marry that girl. Each burger is $19.99 and if you finish the challenge you'll get an O’Toole’s t-shirt!

Ice Cream Challenge
Lindy's Chili and Gertie's Ice Cream: A chili and ice cream shop may seem obscure, but they have an 18 scoop ice cream challenge that is legendary in these parts. That's no typo! 18 scoops of ice cream, 6 bananas, 2 apples, 3 brownies and MORE. You have to finish all this in under an hour to keep your name off the Wall of Shame and hopefully be the (as far as we know) FIRST to earn a place on the Wall of Fame.  

Bacon Bomb
Paddy Long's: The infamous "Bacon Bomb." Need we say more? That sounds either like the most unappealing meal ever or God's gift from heaven to the different food enthusiasts of Chicago. 5 lbs ground sausage, beef and pork wrapped brown sugar bacon. Eat the whole bomb and a large side of fries in just 45 minutes and it won't bomb your wallet, (for those of you who don't understand terrible jokes, that means it will be free) as well as a t-shirt and a spot on the Wall of Fame.

50 Things...
At The Fifty/50, to complete the $50 challenge, you have to eat 50 menu items, which include 30 chicken chicken wings, 5 strips of bacon, 1/2 rack of ribs, onion rings, 7 different sliders and a 50 oz beer. The beer sounds good, but maybe not with the rest of that...? The reward may be enough for you though, because if you finish in 50 minutes or less, the meal is free, you get a t-shirt and you get your picture on the Wall of Fame. $50+50 foods+50oz beer-50minutes=FREE! Even the math is exhausting.

Bringing the Heat? Hot Wing Challenge
Jack Melnick's Corner Tap
: Not one, but two challenges in this house.

  • The XXX Wing Challenge uses the hottest know chili pepper in the world, the Bhut Jolokia. Finish 8 of these spicy mama's, after you sign the waiver of course, and you can end up on their Wall of Flame. Maybe that will be really sexy to all the real hot mama's out there who dine in this joint.
  • If one challenge wasn't enough, they also have an 8 lbs Monster burger challenge at the restaurant. If you and a friend can eat it in 45 minutes or less you'll go home with a t-shirt each and 8 lbs of free burger in your stomachs.

There are millions of other food challenges in Chicago for different cuisines and meals, like burritos, breakfasts, Po'Boys, hot dogs and more, but we're getting hungry and this is all you get - for now. Let us know if we should go on after you've completed these and rounded up just about every t-shirt, free meal and graced every Hall of Fame with that beautiful face of yours. It's a great way to eat for free in Chicago if you're up for the challenge!




Chicago Travel Info

Love to eat, without the pressure? Check out a Food Tour...

Venue Info Price
Progressive Dining Tour Located in The Loop offoffoffoffCulturaloffHistoricHoliday FunoffNightlifeSights of ChicagoRomanticScenicoffoffoff

Adult Price

$85
Details
Tastebud Food Tours ActiveoffoffoffCulturalFamily FriendlyHistoricoffoffoffSights of Chicagooffoffoffoffoff

Adult Price

$39
Details
Chicago Pizza Tours Located in The Loop offoffoffoffoffFamily Friendlyoffoffoffoffoffoffoffoffoffoff

Adult Price

$60
Details
Chicago Food Planet Tours Located in Gold Coast ActiveoffoffoffCulturalFamily FriendlyHistoricoffoffoffSights of Chicagooffoffoffoffoff

Adult Price

$35
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Bikes, Bites & Brews Tour Located in Streeterville ActiveoffoffoffoffoffHistoricoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

$59
Details