11 Private Tours in Chicago to Build a Day Around

1.Private Art Institute of Chicago Skip-the-Line Guided Tour

★★★★★★★★★★5.0 · 275 reviews · 2 hours 30 minutes (approx.) · from $85Our pick

Spend about 2.5 hours with an English-speaking guide such as Heath, Spiro, Samantha, or Mandy, touring the Art Institute’s major works and lesser-known rooms. Your ticket is included, the route can follow your interests, and the museum is wheelchair friendly.

“Heath was masterful! Weaving together hundreds of years of art history with culture, some politics, and a little self-reflection. From details about artists lives, to changes in popular culture, to specifics of paintings and everything in between and around them, Heath delivered a captivating and exciting trip through the Institute.”

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2.Chicago Private Custom City Tour with Hotel Pick Up

★★★★★★★★★★5.0 · 201 reviews · 3 to 4 hours (approx.)

Explore Chicago by private vehicle with a guide and driver, stopping at Millennium Park, the Loop, Lincoln Park, Hyde Park, the University of Chicago, and Wrigley Field. Guides such as Todd, Mike, Matt, and Scott tailor the route to your interests, while downtown hotel pickup keeps the morning simple.

“The guide was super knowledgable and the driver was so smart about which route would get us safely to our destination. We did this tour as soon as arriving to Chicago and we are so glad we did! Thanks for helping to make our Chicago trip memorable!!!”

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3.Private Arrival Transfer from Chicago Airports (ORD) (MDW)

★★★★★★★★★★3.5 · 196 reviews · 1 hour (approx.)

Book a private, one-way ride from O’Hare or Midway to your Chicago hotel or Chicagoland address. Carmel provides a sedan for up to three or an SUV for larger groups, with 24-hour service, luggage help, and driver communication by phone or text.

“Outstanding....driver was very friendly. I will recommend to others whend traveling to Chicago. No issues and was present even I arrived.”

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4.Skip the Line Art Institute of Chicago Tour Semi-Private 8ppl Max

★★★★★★★★★★5.0 · 157 reviews · 2 hours 30 minutes (approx.) · from $85

Spend 2.5 hours inside the Art Institute of Chicago with a guide and no more than seven other people. Expect major Impressionist works, iconic paintings, modern art, and historical context from guides such as Samantha, Heath, Joe, Mandy, and Spiro.

“Loved the Impressionists and the Miniature Rooms collections. Also enjoyed the Andy Warhol gallery and seeing Jackson Pollack’s work.”

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5.Private 45-Minute Chicago Skyline Helicopter Tour

★★★★★★★★★★5.0 · 126 reviews · 45 minutes (approx.)

Fly privately from Schaumburg Regional Airport for about 45 minutes over Chicago’s skyline, Lake Michigan, Wrigley Field, Soldier Field, Millennium Park, Navy Pier, and the city’s famous towers. Pilots such as Steve, Matt, Tommy, Sara, and Chuck provide commentary and help with photos.

“Downtown Chicago is beautiful. Steve was very nice and help took photos of us. Would love to take another flight with him”

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6.Best of Chicago: Architecture & Highlights City Private Tour

★★★★★★★★★★5.0 · 94 reviews

Meet your English-speaking guide beneath the Chicago Theatre sign for a two-hour private walk through central Chicago. Explore the Pedway, Picasso Statue, Riverwalk, Tribune Tower, Magnificent Mile, and Millennium Park, with popcorn, chocolate, and a train pass included.

“Never would have known to "look up" at Macy's. We also went back to the Walnut Room for Mrs. Hering's chicken pot pie.”

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7.Private Departure Transfer to Chicago Airports (ORD)(MDW)

★★★★★★★★★★4.0 · 91 reviews · 1 hour (approx.)

Book a private one-way ride from a Chicago hotel or Chicagoland address to O’Hare or Midway. A chauffeur helps with luggage and takes you to your terminal. Sedans serve up to three people, while SUVs and limousines can carry up to six. Service runs around the clock.

“Before the agreed meeting time, the driver sent me a text message that he was waiting for us. Everything went very smoothly, the driver was elegant and friendly, the car was excellent.”

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8.Art Institute of Chicago Private Expert Guided Tour

★★★★★★★★★★5.0 · 84 reviews · 2 hours (approx.) · from $215

Spend about two hours with a private English-speaking guide at the Art Institute of Chicago. Ask for favorite works, focus on artists such as Van Gogh or Hopper, and see major pieces including Nighthawks, American Gothic, and Seurat’s La Grande Jatte.

“Joe was an amazing guide. Informative and very interesting! Explained the history of the artist as well as the painting.”

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9.Private Transfer Chicago Airport MDW to Chicago Downtown

★★★★★★★★★★3.5 · 54 reviews · 30 minutes to 1 hour (approx.) · from $50

Arrange a private ride from Chicago Midway Airport to your downtown hotel, with airport pickup, an air-conditioned vehicle, a professional driver, and up to 60 minutes of included waiting time. Vehicle type depends on availability and group size, so confirm luggage and car expectations before booking.

“poor communication - driving skills were poor and almost rear ended another car-thank god for sensors on the car as that stopped us.”

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10.ORD Airport Private Transfer to Chicago City|Hotels

★★★★★★★★★★4.2 · 46 reviews · from $40Best value

You get a one-way private ride from Chicago O’Hare to your city hotel in an air-conditioned vehicle. An English-speaking Elife driver tracks your flight, contacts you by phone, WhatsApp, or text, helps with luggage, and waits up to 60 minutes after airport arrival.

“Thank you for great service! The drive to my hotel was smooth! A great start for my first time in Chicago!”

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11.Chicago ↔ Midway Airport, Top Rated Private Sedan Transfer

★★★★★★★★★★5.0 · 18 reviews · 30 minutes to 1 hour (approx.)

You’ll ride from Chicago Midway Airport to a downtown address within five miles of the city center in a private luxury sedan. Echo Limousine tracks your flight, sends driver details by text, and allows 60 minutes of free airport waiting time.

“Driver was very professional, detailed, gave highlights of the city. Will use this company again in the future.”

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