You've probably seen the city from the sky while arriving at O'Hare or Midway, but to get the best views of Chicago's picturesque urban sprawl, you need to take a helicopter tour. Luckily, you don't have to travel far to board an airborne tour of the skyline—did you know there's a heliport in Bridgeport? From 2,000 feet up in the air, you'll be able to take some killer photos of Chicago beaches and Chicago buildings. Prepare to fly with our guide to the top Chicago helicopter tours.
RECOMMENDED: Find more to explore on the best Chicago tours
Soar above the streets of Chicago in a state-of-the-art helicopter during this guided tour (via two-way headset) of the skyline. Your pilot will tell you all about the landmarks you're seeing, from the Shedd Aquarium to Lincoln Park. After 15 minutes (it will fly by, trust us) you'll be back on the ground and itching to see the city from above once more. $165 per person
You can gaze up at Willis Tower (it will always be Sears Tower in our hearts) from the streets or afar, but you'll never really experience its magnificence until you're flying by it at night. The skyscraper is just one the many landmarks you'll see from above on this Chicago Helicopter Experience tour, which departs from a small airport near Bridgeport. $178 per person
Chicago's skyline is beautiful during the daytime, but it's especially stunning when the sun goes down. Enjoy all of the twinkling lights below during Vertiport's night helicopter tour, which offers twilight views of Willis Tower, Navy Pier and other Chicago landmarks. Whether you're capping off a romantic evening or enjoying the sights with a friend, this late night 15-minute flight will leave you with some spectacular Instagram photos. $165 per person
Experience aerial views accompanied only by a pilot on this private helicopter tour, which take off from Chicago's Vertiport. For 15 minutes, you'll be able to look down on the city below you and pretend that you're king of it all. Plus, there will be no one else (except for that pesky pilot) to get in the way of your photos. $349 per person
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