These Chicago food challenges are pretty intense. They evoke the feelings of excitement, jealousy, anxiousness, confidence, doubt, competitiveness. There is something uniquely satisfying about being able to finish a dish that was created with the notion in mind that it is so ridiculous that most will fail. The are a lot of food challenges in Chicago, so we narrowed it down to 10 of the best’ meaning that you will get a physical prize and/or a free meal (sometimes even gift cards).

 

10 Grueling Chicago Food Challenges

 

Rudy’s Famous Skillet Challenger Burger

Rudy’s Bar & Grille
Price: $33 if not completed
Time Limit: 30 Minutes

5.5 lbs of food plated on an iron skillet
Burger topped with a fried egg and a plethora of bacon,’served on a bed of hash browns and fries
Prizes

Free Meal
Free T-shirt
Picture on Wall of Fame
$100 gift card

 

The Fifty/50 Ultimate Eating Challenge

The Fifty/50
Price:’$50 if not completed
Time Limit:’50 Minutes

30 Buffalo Chicken Wings, 5 strips of House-Smoked Bacon, 5 Onion Rings, ‘Triple Secret Burger’ Slider, Turkey Burger Slider, Pulled Pork Slider, Crab Cake Slider, Double D. Grilled Cheese’Slider, PB&J Slider, The Mac, Smoked Ribs (1/2 rack), Baked Potato, and 50 ounces of beer or non-alcoholic drink.
Amatuers Only, No Professional Eaters
Prizes

Free Meal
Free T-shirt
Photo on Wall Of Fame

 

The Big Timmy Burger Challenge

Timothy O’Toole’s
Price:’$20 (price not discounted or free if completed, this is just for the glory)
Great deal for a burger, fries, and shirt.
Time Limit:’One Sitting (which makes it totally doable)

A tall, tall burger with cheese, bacon, lettuce, and tomato
Served with’Irish style fries (similar to loaded cheese fries)
Prizes

Free T-shirt
Picture on Wall of Fame

 

Sandwich Challenge

Lucky’s Sandwich Company
Price:’$27 ( one of three sandwiches free if completed)
Time Limit:’30 Minutes

Pick any 3 of Lucky’s special overstuffed ~1.5 pound sandwiches (meat, coleslaw, and fries on all sandwiches)
Prizes

Free meal if finished under 30 minutes
One sandwich free if finished under an hour
Free T-shirt
Picture on Wall of Fame

 

18 Scoop Beast Ice Cream Sundae Challenge

Lindy’s Chili and Gertie’s Ice Cream
Price:’$50 (if not completed)
Time Limit:’1 Hour

18 scoops of ice cream, 2 apples, 6 bananas, lots of sauces, & some brownies
Vanilla wafers & whipped cream
All topped with some cherries
1 hour time limit
Prizes

Free Meal
Free T-shirt
Picture on Wall of Fame

 

5 Pound Bacon Bomb

Paddy Long’s’Beer & Bacon Pub
Price:’$60′(if not completed)
Time Limit:’45 Minutes

Five pounds of ground sausage, pork and beef mixed with spices and wrapped in a weave of brown sugar bacon. Slow cooked on a pig roaster.
Served with potato salad or fries.
Prizes

Free Meal
Free T-shirt
Picture on Wall of Fame

 

The El Jefe

Taco Village
Price:’$19′(if not completed)
Time Limit:’15 Minutes

~2′ long and is filled with pulled pork and packed withf beans and rice.
Prizes

Free Meal
Free T-shirt
Picture on Wall of Fame

 

Po’Boy Challenge

Fatso’s Last Stand
Price: $50′(if not completed)
Time Limit: 45 Minutes

2 pound of fried jumbo shrimp, coleslaw, pickles, lettuce, tomatoes, special sauce, cheddar cheese sauce, and shoestring fries on a cheddar cheese slathered hoagie. Also’a pound of fries on the side and a 32oz soda.
Prizes

Free Meal
Free Shirt
Plaque on wall
$50 Gift Card to Lockdown Bar and Grill

 

Rockstar Challenge

ROCKS Lakeview
Price:’$30′(if not completed)
Time Limit:’30 Minutes

A 4-layered burger weighing about 3lbs with all of the toppings, served on a pretzel bun with 1lb of fries. 4 pounds total.
Prizes

Free Meal
Free T-shirt
Picture on Wall of Fame

 

Chicago Italian Beef Challenge

Stadium Sports Bar
Price:’$40′(if not completed)
Time Limit:’45 Minutes

A hefty bun loaded with 3 pounds of Chicago beef (thin sliced),’1.5 pounds of Italian sausage (underneath beef),’24 ounces of’jardiniere and sport peppers’and 1 pound of’fries.’You are also required to finish the au jus sauce to wash it all down.
Prizes

Free Meal
Free Shirt
Free Hat
Wall Of Fame
This one may be in East Chicago, IN… but it’s worth the trip if you’re looking for a real challenge!

 

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