Heli Chicago is the city’s longest-running helicopter company, proudly carrying thousands of guests over the lakefront, skyline, and heartland with a flawless safety record. FAA Part 135 certified and flying only turbine and twin-...
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.
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.
Lyla Allison
August 31, 2026
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.
Lyla Allison
August 31, 2026