Chicago Traveler Blog

Chicago Traveler Blog

Chicago Food Challenges Every Eater Should Try

4/10/15 | 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 pizza free! Your reward for finishing a ton of pizza is an "I Conquered 30's Pizza Factory" and most likely a stomach ache. But totally worth it! 

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!

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, brownies and MORE. You have to finish all this in under an hour to keep your name off the Wall of Shame and hopefully earn a place on the Wall of Fame, a free meal, and a free t-shirt!  

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, 5 Onion Rings, "Triple Secret Burger" Slider, Turkey Burger Slider, Pulled Pork Slider, Meatball Slider, Double D. Grilled Cheese Slider, Smoked Chicken Salad Slider, PB&J Slider, The Mac, Smoked Ribs (1/2 rack), Natural Ice 40oz. 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
Jake Melnick's Corner Tap

  • 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.

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...

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