Top Chicago Helicopter Tours

Helicopter Tours

16 results

Best Seller

4.1

(49)

Chicago Helicopter 10-Minute Tour for up to Three Passengers

10 minutesFree Cancellation

from $375

Per group

Take in sweeping views of Chicago from the air during a scenic helicopter flight that offers a premier experience of the Windy City. This private 45-minute flight provides an aerial look at landmarks such as Millennium Park, Navy Park, and Wrigley Field. Ideal for a special occasion, this helicopter tour accommodates up to three people and includes the use of noise-cancelling headsets to hear the pilot clearly.

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4.8

(127)

Private 45-Minute Chicago Skyline Helicopter Tour

45 minutesFree Cancellation

from $849

Per group

Likely to Sell Out

Join us in the daytime or evening for City lights and breathtaking views

Get a front row perspective on the exquisite buildings that line the Chicago River during a 45-minute architecture cruise. Hear live commentary about the history and architectural heritage of Chicago on this family-friendly tour, which highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.

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4.7

(3,108)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

45 minutesFree Cancellation

from $28

Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower), with ease thanks to this prebooked ticket option. Avoid long lines at the ticket office and enter directly to access the highest point in Chicago. Peruse interactive displays and exhibits showcasing Chicago's history. Then walk out on to the Ledge, a glass balcony that offers unimpeded views of Navy Pier and Wrigley Field.

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4.3

(1,810)

Skydeck - Willis Tower Admission

30 minutes to 1 hour 30 minutesFree Cancellation

from $44

Discover the architectural gems of the Windy City from an ideal vantage point—and learn insider facts and stories about the city's top attractions—on this Chicago River cruise. Travel in comfort aboard a boat equipped with both indoor and outdoor seating areas. Covering more than 130 years of architectural history, this tour is the perfect opportunity to see a huge area of the city without the hassle of taxis and public transit.

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4.7

(9,829)

Chicago River 90-Minute Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

Take in views of the Chicago skyline and its landmarks during this Lake Michigan sightseeing boat cruise. Enjoy a laidback ride, soaking up panoramic views from this unique perspective. Listen to audio commentary to give you fresh insight into the landmarks you see, like Navy Pier and the Willis Tower, and feel free to bring your own lunch or grab a drink at the onboard bar (own expense).

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4.4

(905)

Lake Michigan Skyline Cruise in Chicago

30 to 45 minutesFree Cancellation

from $33

Tower above the Windy City’s world-famous skyline with pre-booked admission to 360 Chicago—a great way to avoid long ticket lines. Ascend one of the tallest buildings in North America aboard its lightning-fast elevator, and be rewarded with bird’s-eye views of Chicago and Lake Michigan. You can also upgrade to the Sip and View ticket, which includes one drink at the newly renovated CloudBar. Once onsite, you can purchase tickets to TILT, 360 Chicago's top attraction.

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3.9

(1,231)

360 CHICAGO Observation Deck Admission

1 to 4 hoursFree Cancellation

from $30

4.5

(16)

Chicago Helicopter 25-Mile Tour for up to Three Passengers

15 minutesFree Cancellation

from $650

Per group

Feel the rush of skydiving without going anywhere near a plane, with this indoor skydiving experience in Chicago. Start off with thorough training so you feel confident and know what to expect. Then, enjoy two 60-second ‘free fall’ experiences in a technologically advanced vertical wind tunnel, which feels much like real skydiving. No experience is necessary, and your instructor will give you hands-on assistance when you need.

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4.6

(68)

Chicago Lincoln Park Indoor Skydiving with Two Flights

1 hour 15 minutesFree Cancellation

from $136

Discover the hidden gems of Chicago’s Loop area on a walking tour that showcases the best of the neighborhood’s stunning interiors and architectural must-sees. Step behind the facades to explore beautifully designed interiors—from art deco spaces to stained glass mosaics—as you follow a carefully curated route led by a guide. Along the way, learn about the city’s architecture, art, and history, and experience a side of Chicago often missed by travelers, all from a local’s perspective.

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5.0

(1,568)

Original Chicago Architecture Interiors Tour: Dazzling Interiors

2 hoursFree Cancellation

from $35

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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4.8

(15,924)

Chicago Architecture River Cruise

1 hour to 1 hour 30 minutesFree Cancellation

from $39

Likely to Sell Out

4.7

(2,314)

Chicago Lake and River Architecture Tour

1 hour 30 minutesFree Cancellation

from $45

Taste deep-dish pizza, a Chicago-style hot dog, Italian beef, Garrett’s popcorn & the original 1893 brownie on our top-rated Chicago Food Tours—the ultimate Chicago Culinary Tour experience!

Eat your way through downtown Chicago on a walking food tour. Visit Millennium Park, the Palmer House Hotel, and other city landmarks and taste quintessential Chicago foods such as deep-dish pizza, hot dogs, and chocolate brownies. All food tastings are included, and the tour covers an easy 1.5 miles (2.4 km) suitable for most fitness levels. A bike or kayak rental is also included in the tour cost.

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4.9

(2,027)

Chicago Favorites Ultimate Food and Walking Tour

3 hoursFree Cancellation

from $85

4.6

(3,271)

Chicago Crime and Mob Bus Tour

1 hour 30 minutes to 2 hoursFree Cancellation

from $49

Skip the hassle of planning your Chicago itinerary with this convenient hop-on hop-off tour, covering the city's must-see sights. With multiple strategically located stops, explore the Windy City at your own pace, hopping off to visit top attractions like the iconic Art Institute and famous skyscrapers. Enjoy insightful audio commentary as you cruise through the city, learning about its rich history and vibrant culture. Perfect for first-time visitors or those short on time, this tour offers flexibility and ease, ensuring you don’t miss any of Chicago’s highlights. Book your ticket today and experience the best of Chicago hassle-free!

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3.9

(2,223)

Hop-On Hop-Off Sightseeing Tour by Open-top Bus

2 hoursFree Cancellation

from $44

Likely to Sell Out

Immerse yourself in Chicago's thriving craft beer scene—and visit locals-loved breweries you'd be unlikely to stumble across otherwise—on this half-day brewery tour. Travel in style, and get in the spirit, aboard a traditional Prohibition–style barrel bus. Visit several unique breweries, and go on behind-the-scenes production facility tours. Discover the science behind the brewing process, and enjoy plenty of beer samples throughout the tour.

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4.9

(344)

Chicago Craft Brewery Barrel Bus Tour

3 hours 45 minutesFree Cancellation

from $100

Top Attractions in Chicago

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Attractions

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Not seeing something you are looking for?

It would take days, if not weeks, to see all the sites Chicago offers. Fortunately, Chicago helicopter tours provide a bird’s-eye view of the sprawling metropolis. As you soar over the city, your private pilot will point out the landmarks below and bring you up to speed with what makes them so special. Plus, in the comfort of your chopper, you won’t have to deal with crowds or cold weather. That said, remember that Chicago helicopter tours don’t fly when it’s storming or when the Windy City is too windy.

Top Chicago Helicopter Tours

16 results

Top Attractions in Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

Art Institute of Chicago

The Magnificent Mile

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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