4 Helicopter Flights in Chicago to Plan a Day Around

1.Private 45-Minute Chicago Skyline Helicopter Tour

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

Take a private helicopter flight from Schaumburg Regional Airport toward Chicago’s skyline, with views of Willis Tower, the John Hancock Center, Millennium Park, and both Cubs and Bulls territory. Your pilot provides commentary in English, and in-flight headsets and parking are included. Pilots named on past flights include Matt, Steve, Steven, Tommy, Chuck, and Sara.

“Everything! The experience of this helicopter ride in general will always be memorable. Being able to see the changing of the leaves from above. Matt's knowledge of Chicago, his kindness & patience was truly appreciated.”

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2.Helicopter Tour of Chicago Skyline

★★★★★★★★★★4.6 · 38 reviews · from $188Best value

Meet at Vertiport Chicago FBO for a private helicopter tour with an English-speaking pilot, live commentary, and noise-cancelling headsets. Choose a 10- or 20-minute flight option and look for downtown Chicago, Willis Tower, Navy Pier, the Chicago River, and more. Routes can vary, so a particular landmark is not guaranteed.

“The flight time is relatively short for the price... otherwise, it's great”

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3.Chicago Helicopter 10-Minute Tour for up to Three Passengers

★★★★★★★★★★4.5 · 32 reviews · 10 minutes (approx.)

Fly with Fly Heli from Vertiport Chicago on a roughly 10-minute tour over the Loop, Museum Campus, and Navy Pier. You’ll see the Willis Tower, Chicago River, Soldier Field, and the Ferris wheel from above. The flight takes up to three passengers; pilot Fabio has been praised for making the experience welcoming.

“It was a wonderful and beautiful experience I love seeing the city of Chicago Beautiful lights everywhere”

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4.Chicago Helicopter 25-Mile Tour for up to Three Passengers

★★★★★★★★★★4.5 · 11 reviews · 15 minutes (approx.)

Fly a private 25-mile Chicago helicopter route for up to three passengers, with Willis Tower, Navy Pier, Wrigley Field, and more among the advertised sights. The flight lasts about 15 minutes and starts and ends at Vertiport Chicago. Pilot Nolan has been praised for his clear commentary, but the exact route and weather conditions can affect the day.

“Amazing ! It was perfect ! Too short but perfect ! I love the expérience ! By good sun it’s better ! Champagne ! And if you Walt to get maried they help you !”

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