1. Best Artery-Clogging Frank: Superdawg
Milwaukee Ave.at Devon and Nagle
The Chicago Dog is a belt-busting culinary delight, topped with celery salt, mustard, onions, pepper­oncinis, relish and tomatoes. Fall Out Boy singer Patrick Stump says pick one up at this old-school drive-in. “Never, ever put ketchup on a Chicago Dog,” he adds. “There are rules.”

2. Best Weird-Ass Theater: The Neo-Futurarium
5153 N. Ashland Ave. 
Too Much Light Makes the Baby Go Blind, which stuffs a rotating list of 30 short plays into 60 minutes, plays here. “I’ve seen it 15 times—it’s different every time,”  Stump says.

3. Best Place to Crate-Dig: George’s Music Room
3915 W. Roosevelt Rd.
You may have to fight a rap star for rare vinyl at this hallowed mom-and-pop store. “You see a wall of old photos of Jay-Z standing next to [owner] George,” says MC Lupe Fiasco.

4. Best Spot for Sneakers That Cost as Much as Your Rent: Saint Alfred
1531 N. Milwaukee  Ave.
The go-to boutique for cool kids with an unhealthy fetish for Technicolor footwear.  “It’s tied in to what I call the Sneaker Mafia,” Fiasco says. “I bought these Japanese moccasins there for $350. That’s really, really bad.”

5. Best Club to Stage-Dive: Metro
3730 N. Clark St.
This alt-rock mainstay, located in the shadow of the Cubs’ Wrigley Field, has played host to almost every notable Chicago band of the past 20 years, including Smashing Pumpkins, Liz Phair and Fall Out Boy. “I saw At the Drive-In there, and I swear, Cedric Bixler jumped off this huge stack of speakers and landed in a moonwalk,” attests Stump. “It was the best show I’ve ever seen.”