Helicopter tours in Chicago, United States
Chicago's skyline rises right along the edge of Lake Michigan, and a helicopter flight is the clearest way to see how the Loop's towers, Navy Pier, and the lakefront parks actually connect as one continuous stretch of shoreline.
4 helicopter tours in Chicago, hand-picked and bookable in minutes.
Rated 4.6 from 199 traveler reviews across our listed tours.
Mild, clearest skies
May to October
Cold, more wind delays
November to April
Chicago, Illinois
Private 45-Minute Chicago Skyline Helicopter Tour
This tour is unique as it offers the ability for you and two of your friends or family (a total of 3 passengers) to experience what it is like to fly over the city of Chicago on a 45 minute thrill seeking guided tour. Th
45 min
From $849 USD
Chicago, Illinois
Chicago Helicopter Tour: Loop Tour
Take to the skies and experience Chicago from an entirely new perspective on this extended helicopter tour showcasing the city’s most iconic landmarks, neighborhoods, and waterfront views. The flight begins near the Chic
12 min to 15 min
From $209.99 USD
Likely to sell outChicago, Illinois
Chicago Helicopter Tour: City to Shoreline
Your journey begins with a southeast departure from the Vertiport, offering early views of the city’s iconic skyline. Flying east, you’ll head toward the lakefront and cruise south along the shoreline, passing Soldier Fi
20 min to 25 min
From $349.99 USD
Chicago, Illinois
Chicago Skyline Snap Tour Helicopter Flight Over Chicago
Witness Chicago’s stunning skyline from above on this exhilarating helicopter tour. Departing from the Vertiport, the flight offers breathtaking views of the city’s iconic architecture, including Soldier Field and the Sh
7 min to 10 min
From $149.99 USD
Ways to see Chicago by helicopter
Loop and lakefront scenic flight
A short flight over Soldier Field, Museum Campus, and the Loop skyline.
Extended city and shoreline flight
A longer route that adds Navy Pier, Millennium Park, and Wrigley Field to the skyline view.
Getting there: Tours typically depart from a heliport near the lakefront, such as the Chicago Vertiport south of downtown.
Frequently asked questions
What's the best time to fly in Chicago?
May to October brings Chicago's mildest weather and the clearest skies over the lake, making it the most reliable stretch for flying. November to April is colder, and wind off Lake Michigan, Chicago is a genuinely breezy city, can add delays on top of winter's shorter daylight hours.
What should I bring?
Warm layers for a flight outside of summer, since the wind coming off Lake Michigan makes it feel colder than the temperature alone suggests.
What happens if the weather doesn't cooperate?
Like most operators, tours in Chicago have standard weight and balance limits (you may be asked your weight when booking or checking in), and pilots will delay or reschedule rather than fly in unsafe wind, low visibility, or storms. Booking a tour with free cancellation means a weather delay won't cost you anything.
How much do helicopter tours in Chicago cost?
Prices vary by route, duration, and whether the tour includes a landing, but tours in Chicago currently start from around $149.99. Longer routes, private charters, and landing tours cost more.
Can I cancel or reschedule if my plans change?
Many tours listed here offer free cancellation up to 24 hours before departure, shown as a badge on each listing. Weather-related delays and cancellations are handled directly by the operator through Viator's booking system, and a tour booked with free cancellation won't cost you anything if it needs to be rescheduled.
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Guides for planning your trip
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