The men are tanning along the wide stretch of sand, lined up on their beach towels, and the only hint this isn’t Rio is the hot dog stand selling fat Midwestern wieners. Welcome to Chicago, which seems bent on surprising any remaining bicoastal snobs. How do you counter those creaky clichés of a meat-and-potatoes second city? Start with that snaking spine of Lake Michigan beach, where surfing is now allowed and a prime strip is designated as a gay zone. Follow with some of the country’s most ambitious chefs -- your meat and potatoes are likely to be Wagyu beef paired with some molecular potato-flake whimsy -- and Millennium Park, which features free summer concerts in Frank Gehry’s futuristic stainless steel pavilion. Throw in the Steppenwolf Theatre Company and a constellation of revived neighborhoods. Hipsters will direct you to Wicker Park, Bucktown, and the increasingly gay Andersonville, each crammed with indie cafés and boutiques (though Andersonville’s best lure may be its Swedish Bakery, with its excellent marzipan cream cakes). The beach beefcake will point you to Boystown, anchored by Halsted Street and its row of gay bars and by Unabridged Books, one of the last great independent gay bookstores. But for a lot of locals, the new heart of Chicago is the suddenly thriving South Side, until recently home to the Obamas. You’re not really a second city anymore when, among other bragging rights, you can lay claim to the first lady and her husband too.

THE GROOVE
Roscoe’s
Roscoes.com
More than just the heart of Boystown, North Halsted Steet is one of the Midwest’s prime queer main streets, hosting a strip of gay haunts: the mammoth dance club Circuit; the video bar Sidetrack; and the ultra loungy Mini Bar. Roscoe’s, though, is a bona fide landmark that’s been running long enough to qualify as both your gay uncle’s favorite bar and your own, as it keeps reimagining itself. Current attractions include karaoke, wet-boxer contests, signature Absolut pink lemonade pitchers, and a summer sidewalk café. 3356 N. Halsted St.
(773) 281-3355

Berlin
BerlinChicago.com
If you want to get off the Boystown strip (which can start to feel inbred), Berlin is another local institution, known for its inclusive, neo-hippie vibe and a no-frills boxy dance floor designed for serious movement. Though the crowd can veer toward mixed on weekends, the thumping disco music mostly draws Art Institute students and the bohos who love them.
954 W. Belmont Ave.
(773) 348-4975

THE BED
Park Hyatt
ParkChicago.Hyatt.com
North Michigan Avenue is lined with luxe high-rise hotels like the Peninsula and the Ritz Carlton, but the Park Hyatt is a modernist classic, from its top-drawer art collection (that’s a Gerhard Richter in the lobby) to the Le Corbusier­–meets–Frank Lloyd Wright guest rooms punctuated by black leather Eames lounge chairs. Nab a lakeview room, park yourself in an enormous soaking tub, order from the Butler Bath menu, and gaze out on Lake Michigan through the bathroom’s open sliding doors.
800 N. Michigan Ave.
(312) 335-1234