Chicago, Illinois (2 hours from NYC)
Do this
Chicago boasts two of summer's biggest music tickets—the behemoth Lollapalooza(lollapalooza.com; Aug 6--8; three-day pass $215) and Pitchfork Music Festival (Union Park, 1501 W Randolph St, pitchforkmusicfestival.com; July 16--18; $40 per day). Festival passes are the most painful investment, but Chicago has plenty of budget-friendly hideouts where you can kill time when you're not rocking out in the fields. Nostalgic types will appreciate Lollapalooza headliners Soundgarden, Green Day and the Strokes, while the omnipresent Lady Gaga returns to the fest as well (she first played in 2007). There are tons of recent fan favorites, too, including Arcade Fire, Frightened Rabbit and MGMT. For those with more indie tastes, Pitchfork's lineup stars Pavement, LCD Soundsystem, Modest Mouse, Surfer Blood, Titus Andronicus and more.
In between sets, check out the Rocking Horse (2535 N Milwaukee Ave; 773-486-0011,rockinghorsechicago.com) for a cold beer and classic American fare. Saint Alfred (1531 N Milwaukee Ave; 773-486-7159, stalfred.com) is a required stop for sneaker fiends—you'll need a new pair to keep your dogs from barking during those long hours pressed up against a stage. "They always have the flyest selection of gear and kicks," says local music producer Maker. The store carries everything from limited-edition Nikes and Vans to New York brands Alife and Mishka. Just across the street isReckless Records (1532 N Milwaukee Ave; 773-235-3727, reckless.com), the rumored inspiration for the film version of High Fidelity, where audiophiles can dig through old and new stacks of LPs and CDs. And if it's class you're after, Murasaki Lounge (211 E Ontario St; 312-266-2280,murasakichicago.com) is your oasis, featuring a wide selection of sake, boutique cocktails (try the popular coconut-lemongrass Sake-Lada, $12) and appetizers, plus a private karaoke room. It's also within walking distance of Lollapalooza headquarters at Grant Park.
Stay here
Don't let the name scare you: The House of Two Urns (1239 N Greenview Ave; 773-235-1408,twourns.com; $89--159) is a cheap, convenient alternative to boutique hotels in the downtown Loop area, and offers a free breakfast from 7 to 10am, as well as vegan-friendly meals. It's a short walk to Division Street shops, cafs and restaurants, and one stop on the Blue Line from the barhopping neighborhood Wicker Park.