10 Grueling Chicago Food Challenges for the Brave

man waiting to eat, plate and utensilsThese 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 Challenger Burger in Chicago

RUDY’S BAR & GRILLE

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/50chicken wing Chicago food challenges

Rich M. / Yelp

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 CheeseSlider, 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

Big Timmy Challenge Timothy O'Toole's

Timothy O’Toole’s

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 withIrish style fries (similar to loaded cheese fries)

Prizes

  • Free T-shirt
  • Picture on Wall of Fame

Sandwich Challenge

Lucky's Sandwich sandwiches

Quincy S. / Yelp

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

Lindys Chili and Gerties Ice Cream

Huffington Post

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

bacon bomb at Paddy Long's

Paddy Long’s

Paddy Long’sBeer & 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

EL JEFE chicago food challenge

Taco Village / Facebook

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

Po'Boy Challenge Fatso's Last Stand

chicagoist

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. Alsoa 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

Rockstar Challenge ROCKS Lakeview

ROCKS Lakeview

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

Chicago Italian Beef Challenge Stadium Sports Bar

nwitimes

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 ofjardiniere and sport peppersand 1 pound offries.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!


If you find yourself craving even more, check out Food Challenges (website) for a comprehensive list and reviews of moreChicago Food Challenges!

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Ross Perkins

Ross Perkins is the Executive Editor & a connoisseur of all things enjoyable? at least in his mind. He is an avid traveler in the name of inspiring sights, music, food & cars. He is a published photographer & writer that is looking for any reason to get out and explore his surroundings.

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