Food & Drink

Chicago's 11 Most Ridiculous Eating Challenges

Published On 02/03/2015 Published On 02/03/2015
fatso's last stand
rudy's bar & grille
paddy long's
fatso's last stand
wiener and still champion
FLICKR/WEEZA
FLICKR/KIM
rocks lakeview
timothy o'toole's
jake melnick's corner tap
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1. Rudy's Bar and Grille 69 E Madison, Chicago, IL 60603

A memorabilia-packed burger joint from the pizza-slinging family behind nearby Pizano's, Rudy's offers 3/4lb prime patties like the cheddar/bacon/fried egg Breakfast Burger and much more.

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2. Paddy Long's 1028 W Diversey, Chicago, IL 60614 (Lincoln Park)

Paddy Long's has acquired numerous varieties of Bourbon County Stout for your barrel-aged beer drinking pleasure (which has led to your pleasing barrel shape), tapping this year and last year's original vintages along with variants like vanilla, coffee, and the recently released cherry rye.

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3. Fatso's Last Stand 2258 W Chicago Ave, Chicago, IL 60622 (Ukrainian Village)

This no frills, Ukrainian Village eatery pretty much has the perfect name, with a menu chock-full of items like fresh-cut fries, char dogs, and burgers. One of the staples here is the Double Fatso with cheese -- two perfectly grilled beef patties flanked by slices of American cheese, onion, and secret sauce -- a burger that can give In-N-Out a run for its money.

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4. Wiener & Still Champion 802 Dempster St, Evanston, IL 60202 (Evanston)

More than just a hilarious name, W&SC serves award-winning hot dogs, as well as other sandwiches, burgers, and American grub.

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5. Diner Grill 1635 W Irving Park Rd, Chicago, IL 60613-2526 (Lakeview)

Slinging diner-style fare in Lakeview, The Diner Grill features 'merican grub staples like burgers and breakfast.

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6. The Fifty/50 2047 W Division St, Chicago, IL 60622 (Wicker Park)

The 50's a tri-level sports temple serving gluttonous fare like in-house smoked meats (ribs, pulled pork, wings), mac 'n' cheese toppable with everything from chicken to chili, and the "Double-Secret Probation"-esque "Triple Secret:" a tri-meat fatburger with a classified recipe.

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7. Lucky's Sandwich Co. 3472 N Clark St, Chicago, IL 60657 (Wicker Park)

Lucky's serves up Pittsburgh-style sandos that'll fill ya up, especially if you get a side of their deep-fried hunks of Provolone. Attempt the Lucky’s Challenge, because why opt for just one Pittsburgh-style hulk sandwich with fries and coleslaw in it when you could have THREE stacked with different kinds of deli meats? Devour all overstuffed sandwiches within an hour, and all of 'em are on the house and your pretty mug will live on wall of fame style, which is just as cool as doing it for Man v. Food, right?

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8. ROCKS Lakeview 3463 N Broadway St, Chicago, IL 60657 (Lakeview)

Get some great beer and ROCK-solid bar food (we're so sorry), or cut the nonsense and go straight for the Rockstar Challenge: four Angus beef patties topped with eight slices of bacon, giardiniera, cheese, onion strings, lettuce, and pickles, all on a pretzel bun served with a pound of fries.

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9. Timothy O'Toole's 622 N Fairbanks Ct, Chicago, IL 60611 (Near North Side)

TOT has everything you could want in a dive bar and more: billiards, classic bar food, 48 beers on tap and over 70 HD televisions. The menu offers wings and burger staples as well as healthy options and a children’s menu. Stop in on the weekend for brunch, featuring a Build Your Own Mimosa and Bloody Mary drink bar. This neighborhood pub hosts events such as trivia, karaoke, and comedy nights.

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10. Jake Melnick's Corner Tap 41 E Superior St, Chicago, IL 60611 (River North)

Jake Melnick's Corner Tap is a beer bar in River North, Chicago that's serving up some killer hot wings and other bar foods.