Wicker Park, Chicago
Chicago's Wicker Park neighborhood has gentrified considerably since 1999, when the ode to indie music High Fidelity was filmed there, but the bohemian vibe still lurks (it's just shinier). Many of the places that appeared in the movie don't exist anymore, so we've created an alternative itinerary.
Obviously you'll want to begin your journey at a record store. Stop in at any of the Reckless Records locations and test the clerk's musical mettle. He probably won't be as obnoxious as Jack Black's Barry was in the film, but you could always try. Next stops: Myopic Books for underground comics, then Hot Doug's for a designer hot dog; then, check out who's playing at Hideout that night.
If you prefer a more upscale evening with your sweetie, you can't do better than the 12-course tasting menu at the five-star Alinea in Lincoln Park. If that seems daunting, head over to Avec or Blackbird instead. The two boîtes are next-door to each other — Avec serves gourmet fare with a Mediterranean influence and Blackbird does space-age American food — and both are completely delish. In fact, it's hard to have a bad meal in Chicago. Even run-of-the-mill pizza here is probably better than what you'd get at home.
While there's no shortage of hotels in Chicago (the majority come cheap in winter), most of them are in high-tourist-traffic areas. If you prefer not to book a room at a big-name chain, try a cozy B&B in Wicker Park, like the House of Two Urns or the Wicker Park Inn.
Reckless Records: 1532 North Milwaukee Avenue; 773-235-3727
Myopic Books: 1564 North Milwaukee Avenue; 773-862-4882
Hot Doug's: 3324 North California Avenue; 773-279-9550
Hideout: 1354 West Wabansia Avenue; 773-227-4433
Alinea: 1723 North Halsted; 312-867-0110
Avec: 615 West Randolph Street; 312-377-2002
Blackbird: 619 West Randolph Street; 312-715-0708
House of Two Urns: 1239 North Greenview Avenue; 773-235-1408
Wicker Park Inn: 1329 North Wicker Park Avenue; 773-486-2743