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    1. Local experiences
    2. /Things to do in Schaumburg…
    3. /Aerial Activities
    4. /Helicopter Tours
    5. /45-Minute Chicago Skyline Helicopter Tour
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    45-Minute Chicago Skyline Helicopter Tour

    Fly over Chicago landmarks with a private helicopter for up to 3

    4.9 stars• 62 reviews

    Duration

    45 minutes

    Ideal For

    Up to 3 people

    Includes

    45-min helicopter flight, Skyline views

    Highlights

    Take a 45-minute helicopter flight from Schaumburg Regional Airport to see the Chicago skyline from above. You’ll pass major landmarks like Willis Tower (formerly the Sears Tower) and Navy Pier.

    • Board a private flight for up to three people
    • Fly past United Center, Soldier Field, and Wrigley Field
    • See Navy Pier and the Chicago skyline from the air
    • Skip road traffic by viewing the city from above
    • Check in with valid photo ID if you are 18 or older

    Things to know

    Ages 4+ only. Weight limit is 260 lbs per person, and groups of three must be under 575 lbs total. The credit card used for booking must be presented with matching photo ID.

    Cancellation Policy

    No-shows are charged in full. If you no-show and want to reschedule, a $100 fee applies. If you are late, you may not be guaranteed to fly or reschedule the same day. The operator may reschedule due to FAA Temporary Flight Restrictions, weather, or maintenance; no fees apply.

    Product ID: D5F37U

    FAQs

    You must be at least 4 years old to fly. If you’re 18 or older, bring a valid photo ID for check-in.

    The limit is 260 lbs per person. If you fly as a group of three, your combined weight must be under 575 lbs total.

    Yes. Bring the credit card used for booking and a matching photo ID.

    Meeting details

    Schaumburg Regional Airport

    Experience provided by Heli Chicago

    More about Navy Pier

    Navy Pier stretches out into Lake Michigan like a glittering finger pointing toward the horizon, and from the seat of a helicopter it transforms into one of the most photogenic landmarks in Chicago. The 45-minute Chicago Skyline Helicopter Tour gives you a perspective on Navy Pier that ground-level visitors simply cannot match, with its iconic Centennial Wheel turning slowly against the blue of the lake and the white wakes of boats fanning out from the docks below. As one of the city's most beloved gathering places, Navy Pier anchors the lakefront with a century of history, and seeing it from above puts that scale into immediate, breathtaking context.

    As the helicopter sweeps along the shoreline, Navy Pier appears alongside the rest of Chicago's celebrated skyline, framed by the curve of the lake and the towering silhouettes of the Willis Tower, the John Hancock Center, and Trump Tower. The contrast is striking: the dense vertical canyon of downtown on one side, and the open expanse of water punctuated by Navy Pier on the other. You will see the Ferris wheel from an angle few people ever experience, watch sailboats drift in and out of the marina, and trace the elegant geometry of the pier as it juts into the lake. Every window of the helicopter becomes a postcard, and the ride is smooth enough to soak in every detail.

    This tour is ideal for couples celebrating a special occasion, photographers chasing a unique Chicago shot, visitors who want to see the city in a single unforgettable sweep, and locals who think they have already seen it all. Families with older kids will love the thrill, and anyone fascinated by Chicago's lakefront architecture will find Navy Pier especially rewarding from the air. If you want a memory of Chicago that feels truly cinematic, soaring above Navy Pier and the skyline that surrounds it is hard to beat.

    Related locations

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    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

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    Private Tour

    from $842.70

    Ages 4+ • Up to 3 People

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.9
    Excellent
    62 reviews•Google Maps
    58
    1
    0
    0
    1

    Seeing Chicago from the air is something else entirely, and the pilots here seem to make all the difference. Chuck comes up repeatedly in reviews as a standout, praised for being professional, funny, and genuinely attentive to what passengers want to see during the flight. Pilot Steve gets similar praise. The overall vibe is smooth, safe, and memorable, with many guests saying they'd happily go back for another flight. One thing worth knowing: there was an isolated case where a flight was cancelled last minute due to a pilot calling out, and the customer found out only because they called ahead. It's a rare complaint in an otherwise glowing collection of feedback, but if you're planning around a specific date or special occasion, it's worth confirming closer to your flight day. For anyone who's done Chicago the usual ways and wants something genuinely different, this delivers. The longer tour options get particularly strong recommendations, and repeat visitors seem just as enthusiastic as first-timers. A solid choice for a memorable experience.

    What people are saying

    Review 1 of 5
    5/5

    Matt was our pilot and he was wonderful!!! I surprised my 78 year old mom with a new perspective of the Chicago skyline and Heli Chicago did not disappoint. Easy to navigate there and our pilot Matt was informative, kind and helpful as well as on time :) YES, it is worth the money. An experience we will never forget.

    Photo of Lyla Allison

    Lyla Allison

    August 31, 2026

    Review 1 of 1
    5/5

    Matt was our pilot and he was wonderful!!! I surprised my 78 year old mom with a new perspective of the Chicago skyline and Heli Chicago did not disappoint. Easy to navigate there and our pilot Matt was informative, kind and helpful as well as on time :) YES, it is worth the money. An experience we will never forget.

    Photo of Lyla Allison

    Lyla Allison

    August 31, 2026

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