Chicago
The private bookings: architecture mornings, food crawls and city days set to your pace. The custom routing earns its keep in winter, when outdoor time wants rationing.
Discover Chicago’s highlights on a personalized 3-4 hour private tour. Enjoy hotel pickup, expert guides, and flexible stops to see the Windy City's best.
Most Popular“Great tour! Thank you we recommend it. Professionals. Picked us on time. My family and I loved the experience”
Book this private Chicago airport transfer for a stress-free ride in luxury to downtown hotels. Perfect for travelers valuing comfort, reliability, and hassle-free arrivals.
“Great driver. Extra thanks for waiting so long for our delayed flight! Plane had a flat tire in MPLS, had to wait for another tire to be flown from Chicago to Minneapolis before we could make our flight from MSP to Ohare.”
Experience Chicago from above with this private 45-minute helicopter tour, offering stunning skyline views, key landmarks, and personalized service.
“This was one of the most amazing experiences of my lifeeee I loved every minute of it. I went with a friend and we were so happy with it. Steve was the sweetest !! He made sure me and my friend got a picture we…”
Enjoy a hassle-free, private transfer from downtown Chicago to O'Hare or Midway airports. Comfortable, reliable, and tailored to your schedule.
“Custommer service friendly and experienced and friendly driver. On time pick ups to hotel and back to airport.”
Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.
“Heath has a fascinating and novel perspective as a former art dealer he gave us a whirlwind tour of 500 years of art and the influences driving developments”
Experience Chicago from Lake Michigan on a private sailing trip. Enjoy stunning skyline views, customizable routes, and expert guidance—all in an intimate setting.
“Wonderful way to experience the Chicago skyline Captain Mike was awesome, time flew by and we want to do it again.”
Discover Chicago Fire filming locations on this private tour, visiting iconic sites like Molly's Pub, Firehouse 51, Millennium Park, and more—perfect for fans.
“My wife and I were in Chicago for the marathon and booked the tour for a few days after. Deen kept us well updated both the day before and, on the day, even when delayed in the Chicago traffic but he didn’t cut the tour…”
Discover Chicago’s top eats and architecture on a private 3-hour walking tour, sampling iconic foods and exploring the city's vibrant Loop district.
“Need to walk and be hungry. This was an awesome combination of history of Chicago food but all history.”
Stress-free private transfer from Chicago Midway Airport to downtown for $50. Enjoy air-conditioned comfort and personalized service—ideal after flights.
“For 5 adults, we probably need just a little bigger vehicle. The third row seat was a little tight. But, the driver was great. Would recommend”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“Our guide Dave reached out prior to learn about what we wanted to do and see. He timely met us at our hotel and gave us a GREAT tour of downtown Chicago including lots of history, facts and places we had not considered including the…”
Discover Chicago with a private, customizable guided tour. Explore iconic sights, hidden gems, and enjoy local insights tailored to your interests.
“El Guia tenia buena voluntad, pero falto de motivacion, iniciativa y conocimientos...esperabamos algo mas que un paseo con poco contenido de historia y anecdotas...”
Experience Chicago from Lake Michigan with a private sunset sail. Enjoy customizable routes, stunning skyline views, and personalized service for up to 6 guests.
“The ENTIRE experience was WONDERFUL!!! Including the very accomodating Captain Mike. Thank you all for EVERYTHING!!”
Seamless, private transfer from O'Hare to downtown Chicago in a comfortable SUV. Perfect for stress-free arrivals, with personalized service and upfront pricing.
“Excellent service, on time, clean, very professional driver and safe. Very pleased. Will be using the service again.”
Discover Chicago's top sights on a private 2-hour scenic driving tour, including Wrigley Field, Millennium Park, and stunning lake views—perfect for quick, personalized sightseeing.
“Careful driver, friendly. Took us to all the best sites in Chicago, got some great pictures and memories from our trip here.”
Efficient and comfortable one-way private transfer from Midway Airport to Chicago hotels. Perfect for hassle-free arrivals in a luxury vehicle.
“Very pleased with their friendly & excellent service vMade our arrival very easy & positive highly recommend”
The river runs through an architecture lesson, and the lake applauds.