If you're in town for a limited time, an organized tour may be the best way to get a quick overview of the city's highlights. Some tours -- such as the boat cruises on Lake Michigan and the Chicago River -- can give you a whole new perspective on the city's landscape. Many tours go beyond sightseeing to explore important historical and architectural landmarks in depth. These specialized tours can help you appreciate buildings or neighborhoods that you might otherwise have passed by without a second glance.
Insider Tours -- Free!
Want a personalized view of the city -- aside from your trusted Frommer's guide? A program called Chicago Greeter matches tourists with local Chicagoans who serve as volunteer guides. Visitors can request a specific neighborhood or theme (everything from Polish heritage sites to Chicago movie locations), and a greeter gives them a free 2- to 4-hour tour. (Greeters won't escort groups of more than six people.) Specific requests should be made at least 10 days in advance, but "InstaGreeters" are also available on a first-come, first-served basis at the Chicago Cultural Center, 77 E. Randolph St., from Friday through Sunday. For details, call tel. 312/744-8000 or visit www.chicagogreeter.com, where you can browse a list of specific tour topics.
Started in 1935, Wendella Sightseeing Boats (tel. 312/337-1446; www.wendellaboats.com) operates a 75-minute tour along the Chicago River and a 1 1/2-hour tour along the river and out onto Lake Michigan, pointing out architectural highlights along the way. Tours run April to October. Tickets $39 adults, $35 seniors, $18 kids 3 to 11. See also the Chicago Architecture Center.
Noble Horse (tel. 312/266-7878; http://www.noblehorsechicago.com/) maintains the largest fleet of antique horse carriages in Chicago, stationed around the old Water Tower Square at the northwest corner of Chicago and Michigan avenues. Each of the drivers, outfitted in a black tie and top hat, has his or her own variation on the basic Magnificent Mile itinerary (you can also do tours of the lakefront, river, Lincoln Park, and Buckingham Fountain). The charge is $40 for each half-hour, for up to four people. The coaches run year-round, with convertible coaches in the warm months and enclosed carriages furnished with wool blankets on bone-chilling nights. There are several other carriage operators, all of whom pick up riders in the vicinity.
Chicago Trolley Company (tel. 773/648-5000; www.chicagotrolley.com) offers guided tours on a fleet of rubber-wheeled “San Francisco–style” trolleys that stop at 14 spots around the city. You can stay on for the full ride or get on and off at each stop. An all-day hop-on, hop-off pass costs $39 adults, $19 kids 3 to 11.
It's a bit of a cliché to say that Chicago is a city of neighborhoods, but if you want to see what really makes the place special, that's where you have to go.
The Chicago History Museum offers walking tours of attractions such as Graceland Cemetery and Union Station. Tours depart from the museum at Clark Street and North Avenue. Call tel. 312/642-4600, or visit the museum's website for schedules and to order tickets online.
Groups interested in African-American history should visit Bronzeville (also known as the "Black Metropolis"), the South Side neighborhood where immigrants from the South created a flourishing business-and-artistic community in the 1930s and '40s. Walking and bus tours of the area can be arranged through the Bronzeville Visitor Information Center, 3501 S. Martin Luther King Dr. (tel. 773/373-2842; www.bviconline.info). A locally based company that specializes in black heritage tours, Black CouTours (tel. 773/233-8907; www.blackcoutours.com) offers a "Soul Side of the Windy City" tour, which includes Obama-related sites.
Don't be scared away by the creepy connotations. Some of Chicago's cemeteries are as pretty as parks, and they offer a variety of intriguing monuments that are a virtual road into the city's history.
One of the best area cemeteries is Graceland, stretching along Clark Street in the Swedish neighborhood of Andersonville, where you can view the tombs and monuments of many Chicago notables. When Graceland was laid out in 1860, public parks were rare. The elaborate burial grounds that were constructed in many large American cities around that time had the dual purpose of relieving the congestion of the municipal cemeteries closer to town and providing pastoral recreational settings for the Sunday outings of the living. Indeed, cemeteries like Graceland were the precursors of such great municipal green spaces as Lincoln Park.
The Chicago Architecture Center (tel. 312/922-TOUR ; www.architecture.org) offers walking tours of Graceland on select dates. The tour lasts about 2 hours. Among the points of interest in these 121 beautifully landscaped acres are the Ryerson and Getty tombs, famous architectural monuments designed by Louis Sullivan. Sullivan himself rests here in the company of several of his distinguished colleagues: Daniel Burnham, Ludwig Mies van der Rohe, and Howard Van Doren Shaw. Chicago giants of industry and commerce buried at Graceland include Potter Palmer, Marshall Field, and George Pullman. The Chicago Architecture Foundation offers tours of other cemeteries, including Rosehill Cemetery, suburban Lake Forest Cemetery, and Oak Woods Cemetery, the final resting place for many famous African-American figures, including Jesse Owens, Ida B. Wells, and Mayor Harold Washington.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.