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“The knowledge of Mike was simply outstanding !! TJ and Mike are a great team , my wife and I had plenty of laughs but also we learnt so much about the history of the city.”
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.
“Prompt pick up at the airport even though flight was 30 minutes early. Very friendly and personable.”
Experience Chicago from above with this private 45-minute helicopter tour, offering stunning skyline views, key landmarks, and personalized service.
“Flying over Wriggle Field - Where many family memories were made in the stadium and now over, Go Cubs !”
Enjoy a hassle-free, private transfer from downtown Chicago to O'Hare or Midway airports. Comfortable, reliable, and tailored to your schedule.
“Great driver from downtown Chicago hotel to airport! Very nice and on time. Helpful with luggage! Highly recommend!”
Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.
“Excellent tour - well worth it! Guide was excellent and knowledgeable. Definitely helped to make the most of my visit and appreciate what I was seeing.”
Experience Chicago from Lake Michigan on a private sailing trip. Enjoy stunning skyline views, customizable routes, and expert guidance—all in an intimate setting.
“The sail boat was beautiful and very clean. Captain Ulysses was a great guide and captain. We loved the views of the city from the lake. It was my favorite outing of our trip to Chicago. Our teen kids had a great time too.”
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.
“This is an amazing tour-a must for Chicago Fire fans! Dean is a great tour guide. He showed us several spots where they film the show including Molly's and was able to get us into the firehouse. He also drove us to highlight spots of…”
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.
“We had pick up from ORD to hotel. Had changed to an earlier flight due to weather prediction and notified driver. He responded and was there at the new time to pick us up”
Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.
“First time in Chicago and our excellent tour guide Dave managed to make us discover most of the downtown sightseeing and some hidden gems while explaining the stories and history being them. Very informative and very pleasant experience!”
Discover Chicago with a private, customizable guided tour. Explore iconic sights, hidden gems, and enjoy local insights tailored to your interests.
“Visite agréable avec guide parlant bien le français… aurions aimé un peu plus d’explications culturelles.”
Experience Chicago from Lake Michigan with a private sunset sail. Enjoy customizable routes, stunning skyline views, and personalized service for up to 6 guests.
“Great trip! I would recommend going for longer than 2 hours if you are able. We loved every moment and wished we had booked a longer tour.”
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.
“Our driver was very prompt. The driver was so nice and the car was spotless. Very easy to locate. Dropped us off at the perfect location.”
The river runs through an architecture lesson, and the lake applauds.