Now that the Chicago Cubs are the reigning World Series champs, it might be harder to snag a good seat, but you can typically get a game-day ticket in the bleachers. Even if you can't make a game, take a tour of Wrigley Field. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. To walk on the field and sit in the dugout where Ernie Banks sat is a special experience. Non-game-day tours include stops at the dugout, field and press box (Wrigley Field Tours at mlb.com).
Golfers can glimpse the storied Chicago skyline from both Harborside International and Jackson Park courses, but for an up-close look at some of the city's iconic skyscrapers—from the Art Deco Carbide & Carbon building to the Wrigley Building's impressive clock tower—take an architecture tour on the Chicago River. The Chicago Architecture Foundation River Cruise has onboard docents who will interpret more than 50 buildings along the Chicago River; the vessels are operated by Chicago's First Lady Cruises, which offers a variety of other sightseeing tours. Wendella Boats has been family-run since 1935. Its architecture tour begins on the Chicago River, then ventures through the Chicago Lock on to Lake Michigan for expansive views of Chicago's 26-mile skyline.
Even if you don't step foot on a boat, you can still take in the awesome architecture by strolling along Chicago Riverwalk. The reclaimed riverfront along Wacker Drive is also a nice setting to grab a bite – City Winery and O'Brien's Riverwalk Cafe are two popular spots. RiverWalk is also the launching site for biking and kayaking adventures. Urban Kayaks offers both guided paddles (including a beer tour) and rental kayaks.
If shopping's more your thing, or even if it's not, a walk along Michigan Avenue, or Magnificent Mile, is a fun diversion. Among its landmarks are the Tribune Tower, the John Hancock Center, the Drake Hotel, and the Historic Water Tower. It also has Nike, Tiffany and just about every high-end retailer you can think of. Keep walking south along Michigan Avenue and you'll bump into Millennium Park, on the northwest corner of Grant Park. Cloud Gate, fondly known as the "bean," is mesmerizing. This elliptical sculpture is made of polished stainless steel plates that reflect Chicago's famous skyline and the clouds above it. A city centerpiece, much like New York's Central Park, Grant Park is also home to some of city's great museums, such as the Art Institute of Chicago (Grant Wood's "American Gothic" hangs there) and the Field Museum of Natural History(home to SUE the T.Rex, the largest, most complete T. Rex ever discovered). Visit Artic.edu and fieldmuseum.org for more information.