Lollapalooza’s star-packed lineup is sure to be the weekend’s biggest draw—spanning hip-hop (Outkast, Eminem), EDM (Skrillex), and some of Vogue’s favorite pop stars (Lykke Li, Lorde)—but when you need a break from the festival, its host city offers an abundance of shops, restaurants, and cultural sites to take in. “Chicago may be a large city, but it’s got a small-town kind of friendliness,” says Josh Young of the Chicago-based DJ-duo Flosstradamus, who will play a Sunday-afternoon set. “Don’t be afraid to talk to people on the street and ask for recommendations. Chicagoans love their city and won’t hesitate to steer you in the right direction for whatever it is you’re looking for.”
Pick up festival-ready attire—A.P.C. wedge sandals or Gitman Vintage Hawaiian-print shirts—at Wicker Park boutique Penelope’s (1913 West Division Street; 773.395.2351). In the same neighborhood, choose statement jewelry at Moon Voyage (2010 West Pierce Avenue; 773.423.8853), which features indie designers like Takara and Marcia Moran. Young hits up RSVP Gallery (1793 North Damen Avenue, Lower Level; 773.770.6666), which stocks 3.1 Phillip Lim and Acne Studios alongside up-and-coming streetwear brands like Public School and Off-White. For designer vintage, try McShane’s Exchange (815 West Armitage Avenue; 773.525.0282) in the Lincoln Park neighborhood.