Chicago Private Tours
When you book a private experience with Mike, you know you’re getting a guide passionate about delivering high-quality tours of Chicago
Three Kinds of Private Tours
In-Person Walking Tours
Up to 15 people in your group join Mike for one of the walking tours listed below. These experiences can also be readily customized upon request.
Boat, Bus, and Trolley Tours
If you arrange the transportation, I can give you a great tour experience. I have delivered many boat cruises and can do one wherever you lead it along Chicago’s river and lakefront. If you have an idea for a bus or trolley experience, let me know what you’re thinking and I will do my best to accommodate it, whether it’s a highlights tour or something focused on specific topics or neighborhoods.
Virtual Tours
Up to 1,000 people in your group from anywhere around the world join for a live-streamed version of any of the tour options listed below. This interactive experience encourages attendees to ask their questions along the way, and the recording can also be made available for people to watch later. This is a great option for company events, schools, associations, and other large groups.
Private Tour Options
Ugly Buildings
Ugly Buildings showcases the architecture ignored on all the other tours. This interactive, educational roast lovingly teases these buildings offering a conversation on what makes a design beautiful or ugly. The Chicago Tribune called Ugly Buildings “the local architecture tour that needed to happen.”
Underground Chicago (Plus Rats!)
Discover Chicago’s hidden underside by exploring lower-level streets, train stations, and pedestrian tunnels. Along the way, learn all about the rats who love the city’s underside and gain a new appreciation for these critters who are thoroughly interconnected to Chicago. For this private tour, CTA Single-Ride Passes are sold separately for $3 each to access the subway.
Play Ball: The Wrigleyville Tour
Explore how this iconic neighborhood evolved from an area known for celery farms and cemeteries into the country’s most vibrant sports entertainment districts. This is a great private tour to experience right before seeing a Cubs game in Wrigley Field or a Wrigleyville bar.
Architecture’s Greatest Hits
The most iconic skyscrapers from the Wrigley Building to the Chicago Board of Trade to the Sears (Willis) Tower come together on one fast-paced and fun experience. Discover why Chicago is the country’s architectural capital.
Incredible Interiors
Avoid Chicago’s weather by exploring extraordinary indoor spaces designed between the 1880s and 1930s by Louis Comfort Tiffany, Daniel Burnham, Louis Sullivan, Frank Lloyd Wright, and many others. This tour is especially fun during the Christmas season, because the lobbies are decked out with festive decorations. NOTE: since some of the buildings do not allow live-streamed video, this tour is only available as a private walking tour.
Riverwalk Stroll
Explore the exciting riverwalk, discover Chicago’s history, and check out the views from some of the city’s best architectural vistas.
LGBTQ Stories
Discover Chicago’s LGBTQ (lesbian, gay, bisexual, transgender, and queer) stories in neighborhoods all over the city, including Northalsted (Boystown), Andersonville, the downtown Loop, Bronzeville, and more. These experiences work great as either walking, bus, and trolley tours, and they can readily be customized for your group.
Boat Cruise
If you arrange the vessel and captain of your choosing, I will happily give you a great river and/or lakefront tour wherever it heads. If the boat is small enough, it can be a very interactive experience not possible with the large ships. Ask me whatever questions you have, and I can answer them real-time. It’s a really fun, engaging experience for everyone!
Neighborhoods by Elevated Train
Hop on and off public elevated trains to get unique perspectives of the city. This tour can be customized to feature a mix of Chicago’s wonderful neighborhoods. For this private tour, CTA Single-Ride Passes are sold separately for $3 each to access the elevated trains.
Custom Bus and Trolley Tours
If you tell me where you would like the tour to start/end and the duration, I will create a customized bus or trolley tour just for you. I can also focus the tour on specific themes, including Chicago highlights, LGBTQ stories, Black history, and music history.
Christmas Tours
There is nothing quite like Chicago during Christmastime! The city is filled with festive decorations and wonderful holiday traditions. I can create a custom walking, bus, or virtual tour celebrating the sites you’re interested in seeing. If you’re looking for some ideas to incorporate into your custom experience, click the button below.
Looking for something else?
Is there a different kind of tour you’re looking for? Are you looking for a tour that focuses on a particular architectural style, area of the city, or something else? Fill out the form below and send along your idea. I have been giving all kinds of tours all over the city since 2005 and may be able to help you out. Depending on the tour, the pricing may vary.
Duration & Pricing
All the options above are available as 60, 90, or 120-minute private tours:
60-minute private tour: $200
90-minute private tour: $250
120-minute private tour: $300
If you’re looking for a longer tour, please fill out the form below for a quote.