Chicago Touring With a Twist

From bikes to boats, gangsters to greeters, writer ROBERTA SOTONOFF offers an insider’s rundown of unique ways to explore the Windy City


You are not the average tourist. Sure you like to eat at some nice restaurants. Maybe visit a museum or two. But you have no interest in seeing the city through a tour bus window. With offerings like water, neighborhood, architectural, gangster, bike, and kayaking tours, Chicago can satisfy your desires.


Try Wateriders.The kayaking outfitter combines an upper body workout with fun, history, and architecture. Experience is not necessary, because one of the perks is kayaking lessons.


The city’s earliest residents also paddled down the river but they didn’t get any songs or poetry. In the shadow of the WillisTower (formerly the Sears Tower), your guide will likely pluck his guitar and sing about the wonders of the skyscraper in his own rendition of “Blowin’ in the Wind.”


Fitness and sightseeing are a great combination on terra firma, too. Cycle through Lincoln Park, Grant Park, Chinatown, the lakefront, or President Obama’s neighborhood on an escorted tour. Bike Chicago gives free lakefront tours every afternoon, weather permitting.


The Untouchables Gangster Tour combines the notorious with the nutty. It takes a step back to the days of prohibition and traces the paths of some of the some of the city’s most infamous residents, like Al Capone and John Dillinger. Wisecracking guides relate gangster lore on the way to some of their favorite haunts, including Little Italy and the St. Valentine’s Day Massacre. (Wateriders takes it one step further and lets you glide where the apparitions and thugs hung out on their Shady Chicago: Ghosts and Gangsters of Hustlertown tour.)


Maybe you are not much for the physical stuff or the zany. You know what you want to see and do, but would like to see it through the eyes of a native. The Chicago Greeters program, a free service of the Chicago Office of Tourism (COT), lets you do just that. Friendly Greeters, some of whom are multi-lingual, know the city well and are happy to share nooks and crannies that most visitors never see.


For example, I wanted learn about the work of Mies Van der Rohe. Our Greeter was a veritable fountain of information. She took meon a tour of the IIT campus where the renowned architect taught and designed many of the school’s buildings. Just contact the COT and let them know what you would like to do. Chicago Greeters takes small groups wherever they want to go: shopping, sightseeing, or to interesting city areas.


Culturally diverse neighborhoods have made the city the melting pot that it is today. #Chicago Neighborhood Tours# explore ethnic roots in such areas as Chinatown,Little Italy, Greektown, Brownsville, and Devon Avenue. Once a primarily Jewish neighborhood, Devon Avenue is now a hodgepodge of Pakistani, Israeli, Russian, Assyrian, Thai, Korean, and Indian grocery, bookstores, and restaurants. This little United Nations is a bargain hunter’s paradise for electronics, jewelry, and saris.


The Pullman neighborhood, another Chicago Neighborhood Tour, was created by George Pullman. The designer of the railroad sleeping car transformed his idea that healthy and happy workers would promote higher productivity into this first industrial community. Built in the 1880s, most of the original buildings are still occupied and intact.


The ‘hoods are great, but architecture is a premier attraction. If this is your debut to the Windy City, you need to get on top of things. Catch a scenic glimpse of the city from the Willis Tower Skydeck, where you can step out on “The Ledge,” a suspended glass enclosure on the 103rd floor. For a close-up of the jutting Museum Campus and Navy Pier, visit the John Hancock Observatory. Closer to the ground is the Navy Pier Ferris wheel. Because the wheel turns so slowly, it is easy to get a great photo of the skyline. Weather permitting, take a half-mile stroll down Navy Pier. It’s crowded and touristy, but you’ll find a lot of little shops, the Smith Museum of Stained Glass, and unsurpassed people watching.


The city’s architecture can be explored by bus, foot, and water. Take yourself over to the Chicago River Michigan Avenue Bridge. It offers a wonderful ground level glimpse of the Wrigley Building and the Loop. Equally impressive is the multitude of Chicago Architectural Foundation (CAF) walking tours that weave through the cavernous Loop to investigate entranceways and interesting lobbies. There are a number of other CAF tours, with a variety of venues from cemeteries to buildings by specific architects such as Mies Van der Rohe and Frank Lloyd Wright.


CAF boat excursions give architectural aficionados yet another vantage point. Glide over the Chicago River to examine famous structures from their pylons. The Willis Tower is even more imposing when seen from river level. And if the water’s role in shaping Chicago appeals to you, take a history boat tour.


The HOP ON HOP OFF ride makes it easy to do your own thing. Travel around downtown in a trolley or red double-decker bus. Get on or off at any of 15 locations including Navy Pier, the Museum Campus, or the Mag Mile. Your one-day ticket comes with goodies like a Hershey Bar, a Garrett Popcorn sample, and a discount booklet. From Memorial Day until Labor Day, the three-day ticket (only $6 more) also includes West, South, and Near North neighborhood tours and a T-shirt.


Foodies can forget their diets and savor Chicago culture and its cuisine on the #Chicago Food Planet Tasting & Cultural Walking Tour#. Wander past the Gold Coast’s old stately homes, including Hugh Hefner’s former Playboy Mansion. Discover Old Town and Lincoln Park while stopping along the way to sample tea, spices, pastries, potato pancakes, pizza, and calorific chocolate made by hand. Rationalize it this way: Some of those calories will have dissipated during your walk.


Now, you might want do something to impress your honey. Conjure up a little romance at one of the city’s one-of-a-kind restaurants, like Charlie Trotter’s or TRU. Then take a horse-drawn carriage ride or a Lake Michigan sunset cruise to reassure yourself just how unique Chicago really is.




Most outdoor tours run April through November or Memorial Day until Labor Day.


BIKE CHICAGO  Millennium Park, 239 E. Randolph St.; 312.729.1000 or 888.245.3929,


CHICAGO ARCHITECTURAL FOUNDATION  Starting point is 224 S. Michigan Ave.; 312.922.8687,


CHICAGO FOOD PLANET  Starting point is in the Gold Coast neighborhood, near Michigan Avenue; 800.979.3370,, April/November


CHICAGO NEIGHBORHOOD TOURS  Excursions do not operate on a fixed schedule, so call or check the web first. All tours depart by bus from the Chicago CulturalCenter, 77 E. Randolph St. For reservations, call 312.742.1190 or visit


CHICAGO GREETERS  Contact the Chicago Office of Tourism, 312.744.8000;


CHICAGO TROLLEY & DOUBLE DECKER BUS CO.  Main office is in the Park Shop, Millennium Park. Tickets also available at each stop; 773.648.5000,


UNTOUCHABLES GANGSTER TOUR  Two-hour tours begin at the intersection of Clark and Ohio streets in front of the Rock & Roll McDonald’s; 773.881.1195,


WATERRIDERS  Tours run from the first week in June through late October. Reservations required. Starting pointis Kingsbury Yacht Club on the Riverwalk, 950 North Kingsbury St.; 312.953.9287,



Breaking the Chain

Broughton’s boutique hotels in Lakeview provide a traveler’s alternative to big box lodging


Willows Hotel

A graceful hotel with a European flare and upscale amenities. 555 West Surf, Chicago, 773.528.8400


Majestic Hotel

The tranquility of an English country estate amidst the bustling Chicago city life. 528 West Brompton, Chicago, 773.404.3499


City Suites Hotel

A sleek, retro property characterized by its unique Art Deco style. 933 West Belmont, Chicago, 773.404.3400


For details on each of these properties, see