Chicago Airplane-Helicopter Tours-Sightseeing Tour Options

Chicago Skyline

Chicago Skyline IL

Chicago Interactive Map

Willis Tower

Chicago Willis Tower Illinois

Chicago Air Tours

Chicago Air Tours

Want to experience the Chicago skyline like never before? Book a ride on one of the popular Chicago air, airplane and helicopter tours for an exciting and scenic tour high above the streets of Chicago. A favorite with first-time tourists in Chicago willing to drop a little extra coin on an amazing experience, Chicago air tours put the beautiful architecture of Chicago's most iconic skyscrapers into perspective.

There are a number of Chicago air, airplane helicopter tours options, each with varying Chicago tour rates, departures and durations. Flying out of the small Schaumburg, IL Airport just north of Chicago, Jetway Aviation is one of the biggest Chicago air tours companies. Jetway Aviation Chicago Air Tours run both day and night, and their rates start at $125.00 per person. Chicago attractions featured on Jetway Chicago air, airplane and helicopter tours include the Willis Sears Tower, the famous John Hancock Building, and scenic Navy Pier.

Chicago Helicopter Tours

Chicago Helicopter Tours

Strap on your headset and aviators, and enjoy one of the exciting Chicago helicopter tours offered in the Chicagoland area.

A favorite Chicago air tours company, Rotor Zen Helicopters, a full line of services. Rotor Zen offers the best value tours for the money because they're the only helicopter tour company based within the city of Chicago and are the closest to Downtown. They make it easy to hop aboard and enjoy the ride!

Taking off from the Schaumburg Airport, IL, Chicago helicopter rides from AM Air Service include a tour of Downtown Chicago.

Fly over famous Chicago attractions and landmarks - including historic Chicago sports stadiums like Soldier Field and the Friendly Confines of Wrigley Field - on this most popular air tour of Chicago Downtown.


Chicago Aerial Tours

The Chicago Flightseeing Tour takes off from Midway Airport near Downtown, and gives Chicago tourists a unique perspective of Chicago from more than 3,000 ft. in the air. These popular Chicago air tours generally last just under an hour, and their all-inclusive Chicago tour experience includes a multi-course meal for two at Francesca's Italian Restaurant in Little Italy.

Another popular Chicago air, airplane and helicopters tour company in the Chicagoland area, Magic Carpet Helicopters charter Chicago helicopter tours from Chicago to Milwaukee and everywhere in between. Private tours of Chicago and the upper Midwest start at $235 for one half-hour, and their accommodating on-demand tour service means you pick the time of departure most convenient for you.

For more information on all tours of Chicago, check out our list of Chicago tours and all the Chicago tour deals to go with them!

Chicago Travel Info
  Venue Info Price
Vertiport VIP Helicopter Tours
offoffoffoffoffFamily FriendlyoffoffoffoffSights of ChicagooffScenicoffoffoff

Adult Price

Rotor Zen Helicopters Chicago
offoffoffGrant ParkoffoffHistoricoffoffoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

Gauntlet Warbirds

Adult Price

Chicago Night Helicopter Tour
offoffoffoffoffFamily FriendlyoffoffoffoffSights of ChicagoRomanticScenicoffoffoff

Adult Price

Chicago Balloon Tour
offoffoffoffoffFamily FriendlyoffoffoffoffoffoffScenicoffoffoff

Adult Price


Perfect for adventurous tourists and thrill-seekers visiting Chicago, Chicago air, airplane and helicopter tours are perhaps the coolest way to explore the Chicago skyline and its famous architecture. Experience Chicago landmarks and attractions like never before, as you hover over 3,000 ft. above the streets and sounds of Chicago with popular Chicago air tours.

Chicago air, airplane and helicopter tours offer a unique perspective on all of the best sightseeing in Chicago. Private Chicago air tours are fun, informative, and provide tourists with photo opportunities they won't find anywhere else. See your favorite Chicago attractions - including the iconic Willis Tower Skydeck and historic Soldier Field - from the intimacy of a private charter when you book a Chicago air tour.

While slightly more expensive, Chicago helicopter tours provide a more open-air experience than that of an airplane. Perfect for a special occasion with your loved ones, helicopter rides Chicago can be romantic, exciting and thrilling all in one. Chicago air tours at night, in particular, offer beautiful views of the Chicago skyline lit up at night for an intimate experience unlike any other.

For more information on the best Chicago air, airplane and helicopter tours, use our helpful guide above. These are some of the best things to do in Chicago whether you're here on a romantic getaway, or traveling for fun! To book other top Chicago tours, visit our guide to the best tours in Chicago. Don't think you can afford a helicopter tour in Chicago? Think again! Check out all the best Chicago tour deals so that you can easily pay for one of these!