Chicago: The Chic Starts Right Here
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.
Shops You Can't Find Everywhere
Lori's Designer Shoes: This flagship of a five-location chain stocks Aerosoles along with more niche designs like Castañer espadrilles and 100% boots.
Lili Boutique: Great service and a selection of upscale women's clothing. Highlights include Twinkle tops and dresses, edgy accessories like Dolce Vita shoes and Rebecca Minkoff bags, and designer denim by Earnest Sewn.
Akira: Fun, funky clothes, from designer jeans to $20 blouses, with a wide range of prices and labels, including Hudson, Free People, and Frankie B.
Vive la Femme: For the latest looks exclusively in sizes 12-24, including dresses, jackets, pants, tops, and skirts by Jessica Svoboda and Anna Scholz.
Lenny & Me: An unpretentious consignment shop that's especially good for sexy retro dresses, screen-printed tees, and decades-old accessories.
You Gotta Do at Least One . . .
Gawk at 50 landmarks during the Chicago Architecture Foundation's 90-minute river cruise.
Catch a show at Second City, the comedy club that launched the careers of Tina Fey, Mike Myers, and Amy Sedaris.
Watch the Cubs from Wrigley Field's bleachers, where fans buy each other rounds of beers--making it like the world's largest singles bar.
What's for Dinner?
Rick Bayless cooks authentic Mexican at his world-famous Frontera Grill.
The innovative and mostly vegetarian menu at Green Zebra consists of small plates such as crispy sweet-potato dumplings with water chestnuts and dandelion miso broth.
Japonais is a dimly lit French-Japanese restaurant and lounge. Good for sharing: Le Quack Japonais, a take on Peking duck.
After a kitchen fire in 2006, Pequod's traded its neon signs and White Sox mural for hardwood floors, exposed brick walls, and plasma TVs. Luckily, its thin-crust and deep-dish pizzas stayed absolutely the same. They're served atop whale-shaped boards.
Alliance Bakery and Café has charm to burn, what with a tin ceiling painted gold and 1930s wooden moldings from Poland. Order a key lime bar and sit out front.
Bean There, Done That
Chicago's newest landmark is a shiny, legume-shaped sculpture in Millennium Park that reflects and distorts the city's skyline on its stainless-steel surface. Locals refer to it as The Bean, though British creator Anish Kapoor understandably prefers its real name, Cloud Gate.
Must-See Museum Show
The Art Institute of Chicago's Japonisme exhibit juxtaposes 19th-century European paintings by Degas, Toulouse-Lautrec, Gauguin, and Manet with works by the Japanese artists who influenced them.
Try Something New in Chicago
Learn to sail on Lake Michigan and get stunning skyline views. Chicago Sailing charters from $75 an hour, quad (two-hour minimum). 773/871-7245, chicagosailing.com.