Private Tours


All private tours are fully customized to specific customer needs including; content, route, begin, end, time, length and refreshment options – cost is variable based upon options chosen.

Our tours include a full array of themed walking and bus tours or combination tours with multiple subjects including; history, architecture and popular culture. Our tour hosts are gifted storytellers and interject enthusiasm, energy and humor in their personalized presentations to all guests.

In addition to history, architecture and pop culture content, choose from some of the following themes or request your own specific theme:

Pedway Pub Crawl – explore the mysteries of Chicago’s indoor heated Pedway during the city’s harsh winter while stopping at some of its alluring “watering holes” along the way!

Pedway Brunch Tour – enjoy a delicious brunch at Filini in the Radisson Blu Hotel before setting out to explore the mysteries of Chicago’s indoor heated Pedway during the city’s harsh winter.

South Side Tour featuring “Bronzeville, Kenwood, Hyde Park, Union Stockyards, University of Chicago, Prairie Avenue, Museum Campus

North Side Tour featuring Chicago’s Gold Coast, Old Town, Second City, Lincoln Park, Zoo, Conservatory, Wrigley field, Wrigleyville, Lakeview, Bucktown, Wicker Park, Logan Square, Humboldt Park, Uptown, Green Mill, Aragon Ballroom, Montrose Harbor, Lake Shore Drive, Bloomingdale Trail

West Side Tour featuring Near Westside, United Center, Maxwell Street, Garfield Park & Conservatory, Douglas Park, Route 66, Illinois Medical District, Pilsen, Little Italy

Jewish History Tour featuring Chicago’s south and west sides and migratory patterns to northern neighborhoods and suburbs

Chicago Tragedies Tour featuring the Great Chicago Fire, S.S. Eastland Disaster, Iroquois Theater Fire, Camp Douglas, Haymarket Riot, Our Lady of angels Fire, Union Stockyards Fire, Wingfoot Express Disaster

Immigration Tour featuring myriad Chicago neighborhoods that still define the city’s rich ethnic diversity

Chicago Sports tour featuring stops at all 5 professional sports venues and team history


Our Private tours are perfect for all groups including; corporate outings (collaborative team building), school groups (educational & fun), social clubs, civic organizations, reunions, military, anniversaries and weddings.

All Private Tours content is customized and the tour experience can be further enriched by adding some of the following features; trolleys, dinner, lunch, brunch, cocktails, snacks – just about anything short of a “Blue Angel” fly over!


Lastly, we currently offer two unique VIP private tours for our most discerning guests. Our VIP tours are fully customized and designed with our highly curious guests in mind. In intimate fashion, our VIP tours promise to sate even the most boundless craving for interesting and entertaining information about Chicago! Guests may choose from our “My Kind of Town” Couple’s Retreat walking tour or one of our many City Wide Car Tours. From beginning to end, guests choose their start and end location, content and route taken. All tours are conducted by Dan O’Connell, one of Chicago’s premier tour guides. Dan vows to deliver to each and every guest, a tour experience that they will not soon forget!

Please contact us to book a private tour.

Please call us to make a reservation if you are using a pre-paid voucher or gift card.