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There's Nothing Like the Big City: Chicago

When was the last time you wore heels? The last time you went dancing—other than at a wedding? The last time you ate at a restaurant without crayons on the table? The last time you stayed up past midnight?

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.

Pamper Yourself
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.

Home Base
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.

 
Note: This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.
 

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