Top Chicago Outdoor Activities

100+ results

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

(3,044)

Chicago River 45-Minute Architecture Tour from Magnificent Mile

Free Cancellation
45 minutes

from $28

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

(15,860)

Chicago Architecture River Cruise

Free Cancellation
1 hour to 1 hour 30 minutes

from $39

Likely to Sell Out

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

(9,746)

Chicago River 90-Minute Architecture Tour

Free Cancellation
1 hour 30 minutes

from $45

Marvel at Chicago's iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride. With drone footage, helicopter-mounted cameras, and other custom media, Flyover Chicago creates the sensation of flying above and through the city to take in its highlights from above. Get up close to details atop the highest skyscrapers and learn about Chicago's history and cityscape during the ride.

Free Cancellation
30 minutes

from $38

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

9 days

from $144

4.6

(61)

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Free Cancellation
2 hours

from $85

This self-guided Adventure is perfect for last-minute travelers who love animals and games, and for families traveling with kids! Travelers will use the eATLAS app for directions on where to go, and what to do--map included. You can start and pause the Adventure whenever it is convenient for you. The Lincoln Park Zoo is a 35-acre complex with 200 different species from around the world, and features more than 1,100 animals, as well as programs devoted to conservation, environmental protection and education. Every December, ZooLights brings thousands of visitors to see the zoo at night festively decorated for the holiday season. And it’s all just a few miles north of downtown Chicago! There are eight objectives in our scavenger hunt, encompassing the entire grounds of the zoo, which includes the Nature Boardwalk and Farm-in-the-Zoo. The zoo is open 365 days a year, from 8 AM to 5 PM on the weekdays and 8 AM to 7 PM on holidays. There is no charge for admission.

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3.5

(2)

Lincoln Park Zoo Adventure

Free Cancellation
45 minutes

from $8

Step into Chicago’s coolest hidden bars on a mid-century cocktail adventure! Join a local guide to discover vintage lounges, secret speakeasies, and retro bars most tourists miss. Savor expertly crafted cocktails (own expense), hear untold stories of the city’s nightlife boom, and soak in stylish decor straight from the 1950s and 60s. This small-group tour is perfect for cocktail lovers, architecture buffs, and anyone seeking an off-the-beaten-path night out in the Windy City.

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5.0

(4)

Chicago Hidden Gem: Mid-Century Cocktail Bars Walking Tour

Free Cancellation
1 hour 30 minutes

from $51

Experience the adrenaline rush of skydiving without jumping out of a plane at iFly Chicago-Rosemont. With start times available throughout the day, you can easily find a session that fits your busy schedule. Feel confident after a small-group training session, then head into the tunnel for your solo floats. An instructor is present for both 60-second sessions to give you personalized instruction. Afterwards, take home a flight certificate to commemorate your adventure.

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4.4

(32)

Chicago-Rosemont Indoor Skydiving with Two Flights

Free Cancellation
1 hour 15 minutes

from $131

4.2

(45)

Chicago Helicopter 10-Minute Tour for up to Three Passengers

Free Cancellation
10 minutes

from $375

Per group

An immersive clue-solving adventure around the trendy arts neighborhood Fulton Market. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! Bookings made a week or more in advance receive their kit in the mail. Bookings made less than a week in advance will pick up their kit at the start point on the day of the adventure - exact pickup location is sent after booking.

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4.9

(29)

Outdoor Escape Room in Chicago - Fulton Market

2 hours

from $75

Per group

Delve into the world of natural history with admission to Chicago’s Field Museum. Choose general admission or upgrade to visit one or more special exhibits. Spend as long as you like exploring the museum's extensive collection of artifacts. Get to know SUE, the world's largest T. Rex, or stroll through the sparkling Hall of Gems. Also take advantage of daily tours led by knowledgeable Field Museum docents, free with admission.

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4.6

(502)

Field Museum of Natural History Admission Tickets

Free Cancellation
4 hours

from $29

See the towers, piers and iconic landmarks along the Chicago River on an architectural cruise through the heart of the city. Enjoy complimentary refreshments on deck as you cruise down the historic waterway, while listening to fun stories and facts throughout the tour. Spot gargoyles that keep watch high above the city, and buildings that range from Neoclassical to Art Deco. Take in over fifty sites from Lake Point Tower to the Navy Pier, and see the Second City from the water.

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4.7

(807)

Chicago Architectural River Cruise

Free Cancellation
1 hour 30 minutes

from $50

Likely to Sell Out

Amazing skyline and lakefront views await on our Chicago Bike Tour. Experience the city’s beauty up close on a Bicycle Tour in Chicago that blends culture, history, and unforgettable scenery.

4.9

(236)

Chicago's Ultimate City Bike Tour of Top Downtown Attractions

Free Cancellation
3 hours

from $59

4.2

(32)

Verse Immersive Holographic Theater in Chicago

Free Cancellation
30 minutes

from $40

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

(1,226)

360 CHICAGO Observation Deck Admission

Free Cancellation
1 to 4 hours

from $30

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

(1,797)

Skydeck - Willis Tower Admission

Free Cancellation
30 minutes to 1 hour 30 minutes

from $44

Enjoy a quintessential Chicago experience—and see more of the city's highlights in less time—on an architecture-themed boat tour of the Chicago River. Pick from multiple convenient start times, and board your vessel directly from the Chicago Riverwalk. Thanks to your trained docent guide, receive a rich introduction to the Windy City’s history, key landmarks, and architectural highlights—and spy landmarks like the Marina City towers and Navy Pier from the water’s edge.

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4.9

(5,587)

Chicago Architecture Center River Cruise aboard First Lady

1 hour 30 minutes

from $57

An immersive clue-solving adventure around Old Town. Search for real-world clues, solve puzzles, and discover the neighborhood with an experience you'll never forget! Reschedule anytime with no fees. It's a scavenger hunt, escape room, and urban crawl all-in-one. Follow the storyline around town as you find clues and use them to crack codes. Then enter solutions on the app to find out where to go next. Clues can be anywhere - murals, statues, landmarks, and more! Plan on about two hours of playtime, depending on your experience level and how much time you spend exploring along the way. Difficulty level is adjustable - take as many or as few hints as you’d like! Bookings made a week or more in advance receive their kit in the mail. Last-minute bookings pick it up at the start point on the day of the adventure - exact location sent after booking.

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5.0

(1)

Outdoor Escape Room in Old Town Chicago

2 hours

from $75

Per group

Likely to Sell Out

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

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4.8

(709)

Chicago City Tour with Architecture River Cruise Option

Free Cancellation
2 to 4 hours

from $50

Enjoy a celebratory way to sightsee—and a river cruise like no other—with this evening excursion along the Chicago River. Your modern, glass-enclosed boat makes for a comfortable ride, no matter the weather—and gives panoramic views of Chicago’s well-known architectural gems. As you go, indulge in a gourmet, multi-course meal while enjoying live entertainment, including a DJ and fireworks displays on Wednesdays and Saturdays.

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3.8

(5)

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

Free Cancellation
2 to 3 hours

from $134

See Chicago from a different perspective on this evening cruise that explores the city’s darker side. As twilight settles over the skyline, glide along the Chicago River while hearing chilling tales of disasters, infamous criminals, and eerie legends tied to the city’s past. This relaxed river cruise blends atmospheric storytelling with some of the best nighttime views of Chicago’s renowned skyline and landmarks. Grab a drink from the onboard bar, settle in, and let the city’s shadowy history unfold as you cruise through the heart of downtown. By the end of the journey, you’ll have experienced Chicago’s skyline in a whole new way—while uncovering the chilling events, legends, and mysteries that shaped the city. Please arrive 30 minutes in advance!

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4.0

(105)

Chicago River Ghost & Dark History Night Cruise

Free Cancellation
1 hour 30 minutes

from $46

Likely to Sell Out

4.7

(2,309)

Chicago Lake and River Architecture Tour

Free Cancellation
1 hour 30 minutes

from $45

See Chicago's magnificent skyline at night!

Discover the beauty of Chicago at night during a 1.5-hour cruise on the Chicago River and Lake Michigan. Watch the city sparkle as you pass landmarks such as Museum Campus, Willis Tower, Aon Center and the John Hancock Building, and the illuminated waters of Buckingham Fountain. You'll learn about the history of the city from live commentary by your knowledgeable guide as you glide along the waterfront of Chicago.

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4.4

(293)

Chicago By Night River and Lake Cruise

Free Cancellation
1 hour 30 minutes

from $50

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Top Attractions in Chicago

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When it comes to outdoor recreation, few US cities have as much to offer as Chicago. Choose from an array of Chicago outdoor activities: bike tours through the city's lakefront neighborhoods, Lake Michigan sunset cruises, or architecture boat tours on the Chicago River. Whether you choose to explore on foot, by bike, or by boat, there’s a tour for everyone in the Windy City.

Top Chicago Outdoor Activities

100+ results

Top Attractions in Chicago

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

Chicago Riverwalk

The Magnificent Mile

Art Institute of Chicago

Chicago Theatre

Skydeck Chicago at Willis Tower (Sears Tower)

Chicago River

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