Chicago Tours. A comprehensive collection of Chicago sightseeing tours by air, water, and land can be found through Chicago Tours, a travel-reservation company offering more than 75 tours, cruises, events, and activities. 888/881–3284. www.chicagotours.us.
Get a fresh perspective on Chicago by taking a water tour or cruise. Boat tour schedules vary by season; be sure to call for exact times and fares. The season usually runs from May 1 through mid-November. One cruise in particular stands out, though it's a bit more expensive than the rest: the Chicago Architecture Foundation river cruise aboard Chicago's First Lady, Chicago's Little Lady, or Chicago's Fair Lady. The CAF tour highlights more than 50 architecturally significant sights. The cost is $38 ($35 if reserved online, and $30 for select Tuesdays and Wednesdays); reservations are recommended. Shoreline Sightseeing also runs architecture-themed boat tours.
If you're looking for a maritime adventure, you can get a blast from the past on the tall ship Windy, a 148-foot ship modeled on old-time commercial vessels. Passengers may help the crew or take a turn at the wheel during several different themed sailing cruises of Lake Michigan. The cost is $25 to $45.
Chicago Architecture Foundation River Cruise (312/922–3432 information; 312/922–3432 tickets. caf.architecture.org.)
Mercury Chicago Skyline Cruiseline (312/332–1353 recorded information. www.mercuryskylinecruiseline.com.)
Shoreline Sightseeing (312/222–9328. www.shorelinesightseeing.com.)
Wendella (400 N. Michigan Ave., Chicago, IL. 312/337–1446. www.wendellaboats.com.)
Windy of Chicago Ltd. (312/451–2700. www.tallshipwindy.com.)
A narrated bus or trolley tour can be a good way to orient yourself among Chicago's main sights. Tour costs start at roughly $20 and can last from two hours to a full day. American Sightseeing offers about 30 routes, from classic sightseeing outings to pizza- and blues-themed tours. The double-decker buses of Chicago Trolley & Double Decker Co. vehicles stop at all the downtown attractions. You can get on and off the open-air trolleys as you like; these tours vary in price, so call for details. The Chicago Architecture Foundation's bus tours often go farther afield, exploring everything from cemeteries to movie palaces.
American Sightseeing Tours Chicago Gray Line Prairie Trailways (312/251–3100. www.prairietrailways.com.)
Chicago Architecture Foundation (Tour Center, Santa Fe Bldg., 224 S. Michigan Ave., Chicago, IL. 312/922–3432. www.architecture.org.)
Chicago Trolley & Double Decker Co. (773/648–5000. www.chicagotrolley.com.)
Chicago Tour Guides Institute, Inc. (773/276–6683. www.chicagoguide.net.)
Black Coutours (773/233–8907. www.blackcoutours.com.)
Accenting Chicago Events & Tours, Inc. (312/819–5363. www.accentingchicago.com.)
Chicago Chocolate Tours (312/929–2939. www.chicagochocolatetours.com.)
Untouchable Tours (773/881–1195. www.gangstertour.com.)
Chicago Supernatural Tours (708/499–0300. www.ghosttours.com.)
Bronzeville Visitor Information Center (773/819–5170. www.explorechicago.org/city/en/things_see_do/attractions/tourism/bronzeville_visitor.html.)
Antique Coach and Carriage Company (773/735–9400. www.antiquecoach-carriage.com.)
Chicago Horse & Carriage Ltd. (312/988–9090. www.chicagocarriage.com.)
Noble Horse (312/266–7878. www.noblehorsechicago.com.)
The Chicago Architecture Foundation has by far the largest selection of guided tours, with more than 50 itineraries covering everything from department stores to Frank Lloyd Wright's Oak Park buildings. Especially popular walking tours of the Loop are given daily throughout the year. Chicago Greeter and InstaGreeter (for last-minute weekend visits) are two free city services that match knowledgeable Chicagoans with visitors for tours of various sights and neighborhoods.
Chicago Architecture Foundation (Tour Centers, Santa Fe Bldg., 224 S. Michigan Ave., Chicago, IL. 312/922–3432. www.architecture.org.)
Chicago Greeter (Chicago Office of Tourism, 78 E. Washington St., Chicago, IL. 312/945–4231. www.chicagogreeter.com.)