Where to Stay
Spend a night at the Peninsula Chicago and you'll understand why the local gossip columns frequently report the presence of major movie stars on the premises, although the hotel management declines, of course, to verify such sightings. From its opulent, overscaled lobby to its quietly elegant guest rooms to its serene pool and spa at the top of the hotel--both overlooking the Magnificent Mile and, beyond, Lake Michigan--the Peninsula embodies the tasteful side of grandeur. The bend-over-backward attitude of the staff is one of the property's most distinct features, along with its superb restaurants, Avenues and Shanghai Terrace. Double rooms from $490. 108 E. Superior St.; 312-337-2888; 866-288-8889.
The impressive art collection at the Park Hyatt Chicago, where a massive Gerhard Richter canvas is the lobby's focal point, telegraphs the hotel's demeanor: beautiful and urbane. Rooms are sumptuously furnished, with baths sequestered from sleeping areas by sliding wood panels; and the Nomi restaurant-lounge's outdoor garden is sublime on a summer evening. One small caveat: a regular guest was recently disappointed to discover that the hotel had cut back on complimentary welcome and turndown treats. Little things mean a lot. Double rooms from $325. 800 N. Michigan Ave.; 312-335-1234; 888-591-1234.
With its dynamic swooping form and swank neo-Deco interiors, the Sofitel Chicago Water Tower scores high on the glamour scale. On weekends the young, stylish crowd at the bar spills out into the lobby, and the atmosphere seems more typical of South Beach than Chicago. The Sofitel can feel boisterous, but the reasonable rates (less than what you'd pay at some other top choices) make it appealing. Double rooms from $325. 20 E. Chestnut St.; 312-324-4000; 800-SOFITEL.
If you are a Four Seasons enthusiast, you will be perfectly pleased with its local outpost, although nothing will surprise you. The eclectic period furniture, the Gobelin-style tapestries, the plush floral carpeting and the Imari plates in Chippendale display cases will seem comfortingly familiar. And to a brand loyalist, that's a good thing. Double rooms from $475. 120 E. Delaware Pl.; 312-280-8800; 800-819-5053.
What to Do
After you've checked into your hotel and have settled all your dinner reservations, you'll want to sample the myriad cultural, entertainment and shopping riches that the city offers visitors. Here are a few suggestions for quintessential Chicago experiences:
Discover why the city is called the birthplace of modern architecture: any of the tours given by the Chicago Architecture Foundation provides a fine perspective. The boat trips on the Chicago River are especially recommended for first-timers. 312-922-3432; architecture.org.
Visit Millennium Park. Since opening in 2004, this twenty-plus-acre enclave, near the Chicago Art Institute, has become the city's favorite public space. Among its must-see attractions: the Jay Pritzker Pavilion, a bandshell designed by Frank Gehry; the Crown Fountain, by artist Jaume Plensa; and 312-742-1168; millenniumpark.org.
Take in a show. From regional giants (Steppenwolf, Goodman) to established favorites (Northlight, Lookingglass) to emerging and edgy upstarts (Redmoon, Remy Bumppo, Next), a rich array of theater companies call Chicago home. League of Chicago Theatres; 312-554-9800; chicagoplays.com.
Watch the Cubs play at Wrigley Field. The Friendly Confines has earned its place in the pantheon of Americana, right up there alongside Mom and apple pie. 773-404-CUBS; cubs.com.
Do a little gallery hopping. The major museums--the Art Institute of Chicago (artic.edu) and the Museum of Contemporary Art (mcachicago.org)--are always worthwhile, but in addition there are dozens of interesting contemporary galleries worth checking out, and public art is everywhere (312-649-0064; chicagogallerynews.com).
Attend an outdoor concert. Choose from among the Grant Park Orchestra, in Millennium Park (312-742-7638; grantparkmusicfestival.com); the Chicago Symphony Orchestra, at the Ravinia Festival, in Highland Park (847-266-5100; ravinia.org); and the city's numerous and hugely popular jazz, blues and gospel fests (312-744-3315; cityofchicago.org/specialevents).
Go to an auction. At their best, the sales of 20th-century decorative arts at Wright can give even the New York houses stiff competition. 312-563-0020; wright20.com.
Where to Shop
Chicago is blessed with the best of the top luxury brand names: Hermès, Ferragamo, Ralph Lauren, Bulgari, Gucci, Chanel, Tod's and the like. But don't miss the local one-offs and institutions: for women's apparel, Ikram (873 N. Rush St.; 312-587-1000) and Ultimo (114 E. Oak St.; 312-787-1171); for decorative housewares, Material Possessions (704 N. Wabash Ave.; 312-280-4885) and Elements (102 E. Oak St.; 312-642-6574); and for jewelry, Trabert & Hoeffer (111 E. Oak St.; 312-787-1654), Sidney Garber (118 E. Delaware Pl.; 312-944-5225) and Sabbia (66 E. Walton St.; 312-440-0044).
It's also well worth venturing outside the usual tourist territory to explore the Bucktown neighborhood, where you'll find women's high-style fashion at P. 45 (1643 N. Damen; 773-862-4523), Helen Yi (1645 N. Damen; 773-252-3838) and Robin Richman (2108 N. Damen; 773-278-6150); chic modern home furnishings at Stitch (1723 N. Damen; 773-782-1570); and midcentury European decorative arts at Pavilion Antiques (2055 N. Damen; 773-645-0924).
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