Willie Dixon's Blues Heaven
From 1957 to 1967, this humble building was the home of the legendary Chess Records, a temple of blues and a spawning ground of rock 'n' roll. The Chess brothers, two Polish Jews, ran the recording studio that saw - and heard - the likes of Muddy Waters, Bo Diddley, Koko Taylor and others. Chuck Berry recorded four 'Top 10' singles here, and the Rolling Stones named a song '2120 S Michigan Ave' after a recording session at this spot in 1964.
Art Institute of Chicago
One of the world's premier museums, the Art Institute of Chicago has the kind of celebrity-heavy collection that routinely draws gasps from patrons. Grant Wood's stern American Gothic? Check. Edward Hopper's lonely Nighthawks? Yep. Georges Seurat's A Sunday Afternoon on La Grand Jatte? Here. The museum's collection of impressionist and post-impressionist paintings is second only to those in France.
Sears Tower
The Sears Tower was the world's tallest building right up until the end of the 20th century. Then the Malaysians built the Petronas Towers, and Sears became a has-been. Its self esteem only got worse with Taipei, Shanghai and Dubai putting up even higher towers. Now Sears has an outright Napoleon complex. But it's still the USA's tallest building, and it's still way up in the clouds.
Charlie Trotter's Restaurant
The king of Chicago cooking, Trotter's eponymous restaurant, set in a 19th-century building in Lincoln Park, takes seasonal ingredients in note-perfect directions. Pastry Chef Della Gossett makes the final act here as memorable as the first. Reservations are essential and often required months in advance.
Spin
Though its clientele consists mostly of gay men in their 20s, Spin has become a popular destination for hetero men and women on the weekends. Serious dancers hit the floor, while chatty cruisers orbit the large bar by the entrance. Don't miss Spin's shower contest every Friday night, when hopefuls of both genders bare (almost) all.
Wrigley Field
Built in 1914 and named for the chewing-gum guy, Wrigley Field - aka The Friendly Confines - is the second-oldest baseball park in the major leagues. It's filled with legendary traditions and curses, as well as a team that suffers from the longest dry spell in US sports history. The hapless Cubbies haven't won a championship since 1908, a sad record unmatched in pro football, hockey or basketball.
Huey's Hotdogs
Those who know hot dogs come to Huey's. Regularly ranked among Chicago's top greasy spoons, this gregarious hole-in-the-wall makes a perfect pit stop if you're still peckish after a dainty meal at one of Andersonville's upscale eateries. The shakes here are also legendary.
Navy Pier
Chicago's most-visited tourist attraction, half-mile-long Navy Pier, induces groans from locals about its commercialization. But even they can't refute the brilliant lakefront views, cool breezes and whopping fireworks displays on Wednesdays () and Saturdays ().
Buddy Guy's Legends
You're damned right they got the blues at this premier club, owned by the master himself. Seven nights a week you can hear some of the world's best guitarists crowing that their woman done gone left 'em or that they woke up that mornin' feelin' blue. Sure, there's a touristy feel some nights, but you're almost guaranteed a great show.
Le Bouchon
Classic French defines the menu at this quaint spot, a favorite for neighborhood types seeking a good deal and romantic environs. The lyonnaise salad is a winner, and other faves on the short menu range from escargot to chocolate marquisse (chocolate mousse without the egg whites).
Steppenwolf Theater Company
This legendary ensemble netted a Tony Award in 1985 and put Chicago theatre on the map. It's given the world such actors as Gary Sinise and John Malkovich, and such is the cred of the place that both return for the odd performance. It's very much an actors' company, showing works like True West and David Copperfield.