Best Chicago Tours

Chicago Architecture Tours

Every great city has great buildings, but Chicago is its great buildings. Everything Chicagoans do is framed by some of the most remarkable architecture to be found anywhere. The best way to see the sky-scraping Loop towers or the horizontal sweep of the Prairie School is on one of these top tours.

Chicago Architecture Foundation. The foundation conducts excellent docent-led boat, walking, and bus tours of the Loop and beyond. To get a panoramic view of Chicago's magnificent skyline, try the boat tours. Santa Fe Bldg., 224 S. Michigan Ave., Chicago, Illinois, 60604. 312/922–3432; www.architecture.org. $10 walking tours. Walking tours run year-round; boat tours available Apr.–Nov., daily.

Chicago Greeter. Savvy local volunteers run free two- to four-hour walking tours of the city's neighborhoods and areas of interest, such as fashion, film, and public art. Tours run daily at 10 am and 1 pm and should be booked well in advance. Those who don't sign up in advance for a Chicago Greeter tour can show up for an on-the-spot InstaGreeter tour, offered Friday through Sunday 10 to 4. Tours depart from the visitor information center at Chicago Cultural Center. 77 E. Randolph St., Chicago, Illinois, 60604. 312/744–8000; www.chicagogreeter.com. Free.

Chicago Trolley and Double Decker Co. This hop-on, hop-off ride takes visitors to many downtown and Loop highlights and allows you the flexibility to stop at attractions that catch your fancy. Chicago, Illinois. 773/648–5000; www.chicagotrolley.com. $35.

River and Lakefront Tours

Hop into a boat and sail down the Chicago River for some of the prettiest views of the city. Some tours even head out to the lake for a skyscraper-studded panorama.

You can also hop on a Shoreline water taxi and cruise down the river or on the lake. You won't get running narration, but it's not crowded and it’s affordable—single rides range from $5 to $8 with stops at the Michigan Avenue Bridge, Union Station/Willis (Sears) Tower, Navy Pier, and the Museum Campus.

Mercury Chicago's Skyline Cruiseline. This company does Canine Cruises, where dogs are welcome, and a Chicago by Night tour at sunset. 112 E. Wacker Dr., Chicago, Illinois, 60606. 312/332–1353; mercuryskylinecruiseline.com. $28.

Shoreline Sightseeing. Shoreline's been plying these waters since 1939, and has tours of both the river and Lake Michigan. Chicago, Illinois, 60611. 312/222–9328; www.shorelinesightseeing.com. $35.

Tall Ship Adventures of Chicago. Adventure and education meet on lake tours that illuminate Chicago's maritime history, the life of lake sailors, and environmentalism. Former Mayor Richard M. Daley declared the tall ship Windy the flagship of Chicago. Chicago, Illinois. 312/595–5555; www.tallshipadventuresofchicago.com. $30.

Wendella. See the city at dusk on the Chicago at Sunset tour. There's also a river architecture tour and a combined river and lake tour. 400 N. Michigan Ave., at the Wrigley Bldg., Chicago, Illinois, 60611. 312/337–1446; www.wendellaboats.com. $35.

Kayaking and Canoeing Tours

For a more adventurous spin down the river, rent a canoe or a kayak. Just beware of large boats and crew shells.

Chicago River Canoe and Kayak. This company offers a wide variety of trips, from floats among the skyscrapers to sunset paddles to a nearby island. 3400 N. Rockwell, Chicago, Illinois, 60640-4587. 773/704–2663; www.chicagoriverpaddle.com. $50.

Kayak Chicago. Tours focusing on everything from the city's varied architecture to the nighttime skyline are available at this well-regarded outfit. 1501 N. Magnolia Ave., Chicago, Illinois, 60622. 312/852–9258; www.kayakchicago.com. $65.

Urban Kayaks. At this popular outfitter you can join 90-minute tours of the main branch of the Chicago River. 260 Chicago Riverwalk, Chicago, Illinois, 60601. 312/965–0035; www.urbankayaks.com. $45.

Wateriders. A "Ghosts and Gansters of Shadytown" tour is one of the unique offerings at Wateriders. Kingsbury Yacht Club, 950 N. Kingsbury St., Chicago, Illinois, 60610. 312/953–9287; www.wateriders.com. $65.

Special-Interest Tours

Whether you're a foodie, a history buff, or a shopaholic, there's a custom tour for you.

Chicago Food Planet Food Tours. Sample local delicacies like deep-dish pizza, Polish pastries, Chicago-style hot dogs, and Szechuan cuisine on a Near North, Bucktown–Wicker Park, or Chinatown food-and-cultural tour. Chicago, Illinois. 312/818–2170; www.chicagofoodplanet.com. $35.

Untouchable Tours: Chicago's Original Gangster Tour. Your guides, in character as Prohibition era goons, take you on a bus tour through Chicago's checkered mafia past. Though the kitsch factor is high, the tours are stuffed with history and will take you to neighborhoods you might otherwise miss. Chicago, Illinois. 773/881–1195; www.gangstertour.com. $30.

Behind the Scenes

For a look at what (or who) makes the city tick, check out the following activities.

Federal Reserve Bank of Chicago. The facility processes currency and checks, scanning bills for counterfeits, destroying unfit currency, and repackaging fit currency. A visitor center in the lobby has permanent exhibits of old bills, counterfeit money, and a million dollars in $1 bills. One-hour tours at 1pm every weekday explain how money travels and show a high-speed currency-processing machine. 230 S. LaSalle St., Loop, Chicago, Illinois, 60610. 312/322–2400; www.chicagofed.org. Free.

Goose Island Brewery. Follow a brewer on a tour of this well-known Chicago brewery producing handcrafted lagers, ales, and vintage ales. During the tour you'll sample six beers from the current rotation and receive a souvenir pint glass to take home. Reserve at least a week in advance. Tour participants must be 21 or older with valid ID. 1800 N. Clybourn Ave., Lincoln Park, Chicago, Illinois, 60614. 312/915–0071; www.gooseisland.com. $10.

Graceland Cemetery. A comprehensive guide available at the entrance walks you by the graves and tombs of the people who made Chicago great, including merchandiser Marshall Field and railroad-car magnate George Pullman. 4001 N. Clark St., Far North Side, Chicago, Illinois, 60613. 773/525–1105; www.gracelandcemetery.org. Free.