World City Guide

Tours of the City

See Chicago by boat, train, coach, bicycle and antique carriages. Many excursions are slanted toward a special interest – such as architecture, neighbourhoods, and some are themed, like gangster tours. Full listings are available from hotel concierges and from the city’s website (www.cityofchicago.org or www.choosechicago.com).

Walking Tours

Chicago Architectural Foundation Tours (walking and boat)
The city is known for its architecture and there is no better way to learn about the city’s structural designs than by taking one of the many tours that the Chicago Architectural Foundation offers. Tours are on foot, by bus and on the water and include historic and modern skyscrapers and Frank Lloyd Wright homes. Except for the water tours, most begin at 224 South Michigan Avenue (tel: (312) 922 TOUR (8687); website: www.architecture.org).

Chicago Greeters
Considered a ‘themed visit’ rather than a tour, Chicago Greeters will escort small groups (up to six) to attractions, neighbourhoods, explore insider’s favourite haunts, visit specific points of interest, or even take them shopping. Greeters are residents who know and love the city. Chicago Greeters is a free service of the Chicago Office of Tourism. Advance reservations are necessary (tel: (800) 226 6632; website: www.chicagogreeter.com).

Chicago Neighborhood Tours
Explore the city’s cultural diversity on a Chicago Neighborhood Tour. Tours include ethnic neighbourhoods like Chinatown, Little Italy, Greektown, Brownsville and Devon Avenue, as well as specialty excursions like The Great Chicago Fire and the Pullman neighbourhood (the first industrial community). Schedules are sporadic and reservations are necessary. Departure is from the Chicago Cultural Center (tel: (312) 742 1190; website: www.chgocitytours.com).

Loop Tour Train
A unique way to learn about the city’s architecture is via the Loop Tour Train. The tour, aboard the CTA ‘L’ train, circles the Loop three times, while a Chicago Architecture Foundation docent explains the beauty of the faades and windows that hide amid the caverns of the city. These free Saturday tours, which operate from May – Sep, originate at the Chicago Cultural Center on a first-come, first-served basis (tel: (877) CHICAGO (244 2246); website: www.ci.chi.il.us/Tourism/ThingsToDo/LoopTourTrain).

Water Tours
One of the best ways to appreciate the beauty of the city as well as learn about it is from the water. Water excursions operate May- through early Nov, but it is best to check with the individual sightseeing company for schedules and costs. From May- Nov, tours offered by the Chicago Architectural Foundation (tel: (312) 922 TOUR (8687); website: www.architecture.org) give a pylon prospective of Chicago’s great structures, as does Chicago First Lady (tel: (847) 358.1330; website: www.cruisechicago.com). Chicago from the Lake Boat Tours (tel: (312) 527 1977; website: www.cfl81.com) also runs both history and architectural trips. Other water cruises include: Wendella boats (tel: (312) 337 1446; website: www.wendellaboats.com) which depart from below the Wrigley Building and cruise the Chicago River and Mercury (tel: (312) 332 1353 or (312) 332 1368; website: www.mercuryskylinecruiseline.com) which offers a 90-minute lake and river cruise for US$17.

Boats departing from Navy Pier run the gamut from schooners to yachts and those that include meals and cocktails. Enjoy the Odyssey (tel: (708) 990 0800; website: www.odysseycruises.com) or Spirit of Chicago (tel: (312) 836 7899; website: www.spiritcruises.com). Year-round departures. Windy I or Windy II set sail around Lake Michigan (tel: (312) 595 5555; website: www.tallshipwindy.com).

Paddle a kayak down the Chicago River with Wateriders (tel: (312) 953 WATR (9287); website: www.wateriders.com), and explore history, architecture or gangster history, or try Metro Ducks (tel: (800) 298 1506; website: www.metroducks.com), a land-and-water cruise on vintage WWII crafts. For a little romance, cruise down the river with Old World Gondoliers (tel: (312) 543 5819; website: www.4gondola.com). The gondola comes with an Italian-singing gondolier and a rose for the ladies.

Bus Tours
There are plenty of road-based options for touring the city. Gray Line Tours (tel: (312) 251 3100 or (800) 621 4152; website: www.grayline.com) runs a variety of city excursions including ‘North’ and ‘South’ side city tours, which cover all the major sights in those parts of the city. Buses leave from 55 East Monroe Street. A single, two-hour tour costs US$20, or combine both tours for US$40. Chicago Motor Coach Co (tel: (312) 666 1000; website: www.planetdata.com/doubledecker) offers 90-minute tours of the Downtown area, in double-decker buses for US$13, concessions available. The hop-on hop-off service stops at a number of points, including Navy Pier, Sears Tower, the Art Institute and Field Museum. The Chicago Double Decker Co. (tel: (773) 648 5000; website: www.chicagotrolley.com), based at the Sears Tower, offers a similar service, using London-style double-decker buses to tour 21km (13 miles) of Chicago's main sights. An all-day hop-on hop-off ticket costs US$20.

Untouchable Tours
The Untouchables Gangster Tour (tel: (773) 881 1195; website: www.gangstertour.com) takes a step back to the days of prohibition. It traces the paths of some of the city’s most infamous 1920s and 1930s residents, like Al Capone and John Dillinger. Wisecracking guides relate gangster lore on the way to famous hoodlum haunts like Little Italy and the St Valentine’s Massacre. All tours depart from 600 North Clark Street, and reservations are necessary. Cost: US$24.

Tours of Bronzeville, a particularly significant neighbourhood for Chicago’s African-American history, are conducted by Black Metropolis Convention and Tourism Council (tel: (773) 548 2579; website: www.bronzevilleonline.com).