Chicago

15 Best Chicago Private Tours

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.

1.Chicago Private Custom City Tour with Hotel Pick Up

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★ 5.0

“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.”

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5.Art Institute of Chicago Private Expert Guided Tour

Discover the art masterpieces of Chicago with a private, expert-guided tour at the Art Institute, including skip-the-line access and tailored insights.

★ 5.0

“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.”

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6.Private Sailing on Beautiful Lake Michigan – Navy Pier, Chicago

Experience Chicago from Lake Michigan on a private sailing trip. Enjoy stunning skyline views, customizable routes, and expert guidance—all in an intimate setting.

★ 5.0

“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.”

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7.Private Chicago Fire TV Show Set Tour

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…”

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9.Private Transfer Chicago Airport MDW to Chicago Downtown

Stress-free private transfer from Chicago Midway Airport to downtown for $50. Enjoy air-conditioned comfort and personalized service—ideal after flights.

★ 3.5

“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”

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10.Your Way or the Highway: 2-hour Customized Private Walking Tour in Chicago

Discover Chicago through a personalized 2-hour private walking tour. Customizable routes focus on art, architecture, food, and hidden gems with expert guides.

★ 5.0

“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!”

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12.Serene Private Sunset Sail on Lake Michigan – Navy Pier, Chicago

Experience Chicago from Lake Michigan with a private sunset sail. Enjoy customizable routes, stunning skyline views, and personalized service for up to 6 guests.

★ 5.0

“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.”

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14.Private Chicago Scenic Driving Tour

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.

★ 5.0

“Careful driver, friendly. Took us to all the best sites in Chicago, got some great pictures and memories from our trip here.”

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More Chicago Private Tours

5.0Private Chicago P.D. TV Show Set Tour2 hours (approx.)$315.00 5.0One-Way Private SUV Transfer from Downtown Chicago to O’Hare30 minutes to 1 hour (approx.)$155.00 4.5Round Trip Private Transfer ORD Airport to Chicago City Oak Brook20 to 40 minutes (approx.)$91.66 5.0Private Chicago History Museum Tour2 hours (approx.)$162.50 5.0One-Way Private Transfer from Downtown Chicago to ORD by Sedan30 minutes to 1 hour (approx.)$133.00 4.5One-Way Private O’Hare Airport Meet and Greet Transfer by SUV30 minutes to 1 hour (approx.)$200.00 5.0Private Sedan Transfer from Chicago Downtown to O`Hare airport30 minutes to 1 hour 30 minutes (approx.)$220.00 4.8Chicago: Private 3-Hour Al Capone Gangster Tour3 hours$880 3.0Private Chicagoland One-Way Transfer by Mercedes Sprinter$228.94 5.0Chicago: 3-Hour Private Speakeasy Cocktail VIP Tour3 hours$950 4.0Chicago: Private Architecture Tour – 3 or 6 Hours$780 5.0Chicago Private Architecture Walking Tour3 hours (approx.)$211.00 5.0Chicago Private Foodie Tour: Windy City Faves4 hours (approx.)$288.00 5.0One-Way Private ORD Airport Meet and Greet Transfer by Sedan30 minutes to 1 hour (approx.)$154.00 4.5Private Frida and Friends Tour in Pilsen2 hours (approx.)$240.00 4.5Chicago 4-Hour Sightseeing Transfer by Luxury Private Sedan4 hours (approx.)$190.00 5.0Private Chicago Guided Tour with Hotel Pickup4 hours (approx.)$844.59 4.0One-Way Private Airport Transfer by Sedan30 to 45 minutes (approx.)$179.00 5.0Private SUV Transfer from Chicago Downtown to O`Hare airport30 minutes to 1 hour 30 minutes (approx.)$240.00 5.0Chicago O`Hare Airport (ORD) to Chicago hotel/address – Arrival Private Transfer35 minutes (approx.)$75.69 5.0One-Way Private Curbside Midway Airport Transfer by SUV30 minutes to 1 hour (approx.)$155.00 5.0Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class1 hour 30 minutes (approx.)$59.00 3.9Chicago Highlights Private Walking Tour With A Guide2 hours$129 4.5Chicago Private 3-Hour Luxury SUV and Chauffer3 hours (approx.)$360.00