There's Nothing Like the Big City: Chicago
Where to Kick Up Your Heels
Twilight entertainment: Castaways Bar & Grill, on the North Avenue Boathouse's rooftop, serves electric lemonades and piña coladas from a bar decorated with fishing nets and fake lobsters--but the real lure is the view of the bathing-suit-clad crowds on Lake Michigan's North Avenue Beach.
Grown-up drinks: At warm and mellow Clybar, couches surround a hand-carved cherrywood fireplace, and fiber-optic lights in the ceiling create a starry sky. The martinis come in interesting flavors like pomegranate-lemon and chocolate-cherry.
Outdoor seating: Sheffield's is an open-air beer garden with picnic tables in an ivy-covered courtyard; it's regularly packed with a young professional crowd.
Till midnight: Strange memorabilia, antiques, and found art line the walls of Old Town Ale House, a dive where the jukebox plays jazz, blues, and Sinatra.
Till 3 A.M.: Serious partiers let loose on Friday nights with live-band karaoke at Wicker Park's Pontiac Café & Bar. It's a modest setup (black plastic chairs, lone disco ball), but the fun is world-class.
Something you'll regret: Frat guys, bachelorettes, and bikers get down at Hogs & Honeys, a saloon with a mechanical bull and three stripper poles.
Its Loop location targets professionals, but Spa Space's top-notch technicians draw clients from all corners of the city. The wine-and-roses manicure comes with an antioxidant-rich grape-seed scrub and rose-oil massage.
Downtown's Hotel Monaco serves fresh-baked cookies in the afternoon and wine every evening--and has plush animal-print robes hanging in every room.
A block from the Magnificent Mile, The James specializes in high-tech minimalism: Double rooms have slate-tiled bathrooms, martini shakers, and iPod docking stations.
Majestic Hotel, on a tree-lined street in Lakeview East, charms guests with antique-style beds and tapestries. Suites fit up to five and have kitchenettes with a wet bar, fridge, and microwave.
We Love Brunch
Ina's is wildly popular for its comfort food--and if it was a long night, you simply have to try the scrapple. Best of all, the restaurant (located in the West Loop) has a patio.