1. Po'Boy Challenge
Fatso's Last Stand (address and info)
Approximate calorie count: 3,624
Your eyes are not deceiving you. That is a SEVEN-POUND sandwich and A POUND of fries. And if you wanna get your name on a plaque (who doesn't?!?), you're gonna have to finish the whole damn thing. Plus a 32oz soda. Stuffed between that solid slab of bread is 2lbs of fried shrimp, coleslaw, tomatoes, pickles, lettuce, special sauce, cheese sauce, and shoestring fries. In case that other measly pound of potatoes wasn't sufficient. Should you complete this chubby challenge, it really will be the last time you stand for a while. But after a feat like that, you sure as hell deserve to lie down.
Chicago's also got a bunch of other gluttonous food challenges for you to attempt...
Rachel Freeman is a Food/Drink editorial assistant at Thrillist, and would definitely fail at every food challenge, unless it involved eating an entire wheel of cheese. Then she would definitely win. Follow her to the crackers: @rachelifreeman.