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Top Chicago Outdoor Activities

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86 results | All Chicago Tours

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90-Minute Chicago River Architecture Tour
Likely to Sell OutLikely to Sell Out

90-Minute Chicago River Architecture Tour

star-4.5
2816
Discover the architectural gems of the Windy City from an ideal vantage point on a cruise down the Chicago River. Offered several times throughout the day, it’s easy to fit the leisurely excursion into your itinerary. Covering more than 130 years of architectural history, the 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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  • 1 hour 30 minutes
  • Free Cancellation
From
US$42.00
From
US$42.00

Chicago Architecture River Cruise

Chicago Architecture River Cruise

star-5
9672
Cruise down the Chicago River to see the city's famous architecture on this boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including more than 40 notable buildings like Navy Pier, the Wrigley Building, and the John Hancock Building. Cover all three branches of the Chicago River, passing the East Bank Club, the old Post Office Building and the Willis Tower (formerly known as the Sears Tower).
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  • 1 hour
  • Free Cancellation
From
US$46.87
From
US$46.87

Lake Michigan Sightseeing Cruise
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Lake Michigan Sightseeing Cruise

star-4.5
530
Take in iconic views of the beautiful Chicago lakefront and its many landmarks during this Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's skyline from a unique perspective. Along the way, you'll listen to informative commentary and take in views of the John Hancock Center and Willis Tower, along with many other landmarks. Plus feel free to bring your own lunch or grab a drink at the onboard bar, during your ride.
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  • 40 minutes
  • Free Cancellation
From
US$28.34
From
US$28.34

Chicago Lake and River Architecture Tour

Chicago Lake and River Architecture Tour

star-4.5
1054
Step aboard a boat for a comprehensive cruise that details the history of Chicago's architecture. Enjoy views of the Chicago skyline accompanied by architecture-focused commentary that points out each of the landmark buildings. As you cruise through Lake Michigan, snap photos of you and your party against the stretch of Chicago's 26-mile shoreline.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$42.00
From
US$42.00

45-Minute Chicago River Architecture Tour from Magnificent Mile
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45-Minute Chicago River Architecture Tour from Magnificent Mile

star-4.5
369
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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  • 45 minutes
  • Free Cancellation
From
US$27.00
From
US$27.00

Chicago Sunset Cruise

Chicago Sunset Cruise

star-4.5
507
Drink in a one-of-a-kind perspective on the Windy City when you go for an evening cruise, perfectly timed to coincide with the sunset. Hop aboard your open-top vessel in the heart of the Magnificent Mile, and cruise along the Chicago River, where your guide will point out architectural highlights. Then, see the skyline from a distance, and watch the skyscrapers light up, when you continue to Lake Michigan for a sunset viewing.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$42.00
From
US$42.00

360 CHICAGO Observation Deck Admission (Hancock Center)

360 CHICAGO Observation Deck Admission (Hancock Center)

star-4
419
Tower above the Windy City’s world-famous skyline with admission to 360 Chicago (John Hancock Observatory). Ascend 94 stories to the observation deck of one of the tallest buildings in North America aboard its lightning-fast elevator. Then check out bird’s-eye views of landmarks like the famous Willis (Sears) Tower and the lakefront shoreline, and enjoy a variety of educational exhibits on site. Upgrade your ticket to include TILT, a thrill ride that offers visitors unique, downward facing views from 1,030 feet. Or, choose the Sun and Stars package for two visits to the observation deck within 48 hours. With mobile tickets, simply scan your phone for direct entry into 360 Chicago.
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  • 1 to 4 hours
  • Free Cancellation
From
US$30.00
From
US$30.00

Skydeck Chicago Admission Ticket

Skydeck Chicago Admission Ticket

star-4
1075
Visit the Skydeck, located on the 103rd floor of the Willis Tower (formerly the Sears Tower) with this pre-paid admission ticket. From the highest point in the city, look out on Chicago's skyline for panoramic views of the sprawling Windy City. Peruse the interactive displays and exhibits showcasing Chicago's history, which are geared toward curious learners of all ages. Then walk out on to the Ledge, a glass balcony that allows views of Navy Pier and Wrigley Field from one of the world's tallest buildings, standing 1,353 feet (412.4 meters) tall.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
US$44.00
From
US$44.00

Gangsters and Ghosts Tour in Chicago

Gangsters and Ghosts Tour in Chicago

star-5
3538
Experience a colorful side of Chicago history with this Gangsters and Ghosts Tour. With a historian as your guide, you’ll step back to the roaring 20’s, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
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  • 2 hours
  • Free Cancellation
From
US$35.00
From
US$35.00

Big Bus Chicago Hop-On Hop-Off Tour

Big Bus Chicago Hop-On Hop-Off Tour

star-4
1313
Don’t spend time figuring out what to see in Chicago and how to get there—this hop-on hop-off tour provides a mapped-out itinerary of the city's top sights. With several strategically located stops, the tour allows you to explore the Windy City at your own pace. See the world-class Art Institute and landmark skyscrapers, while audio commentary onboard gives you insight into the city's colorful history.
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  • 1 hour
  • Free Cancellation
From
US$44.99
From
US$44.99

Chicago Crime and Mob Bus Tour
Likely to Sell OutLikely to Sell Out

Chicago Crime and Mob Bus Tour

star-4.5
1700
Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.
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  • 1 hour 30 minutes to 2 hours
  • Free Cancellation
From
US$46.00
From
US$46.00

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

Go City: Chicago Explorer Pass - Choose 2, 3, 4, 5, 6 or 7 Attractions

star-4
248
The easiest and most affordable way to explore some of Chicago's top attractions at your own pace, the Chicago Explorer Pass by Go City saves you up to 40 percent off compared to buying individual attraction tickets. Create your own sightseeing itinerary by choosing 2, 3, 4, 5, 6 or 7 attractions, tours, and activities from among more than 25 top sites, including SkyDeck, 360 Chicago, the Field Museum, a shoreline sightseeing cruise, a hop-on hop-off Big Bus tour, Lincoln Park Zoo, Navy Pier, and LEGOLAND® Discovery Center. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two years from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 60 days and/or the remaining number of attraction choices purchased.
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  • 60 days
From
US$68.00
From
US$68.00

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

Skyline Tour Aboard 148 Ft. Schooner Windy - Chicago's Official Tall Ship

star-4.5
339
Escape the bustle of the city on a sailboat tour through Lake Michigan with a convenient departure from Navy Pier. The cruise offers plenty of frame–worthy photo opportunities, including sweeping views of the Chicago skyline rarely seen by visitors. As a popular choice for both locals and visitors, your experience is guaranteed to be family–friendly and tailored to your needs. Select from Pirates and Maritime Stories Sail at 1pm, Skyline/Architectural Theme at 3pm and 5pm, and Skyline Sunset Sail at 7pm. This sail is approximately 75 minutes. The ship leaves promptly at the scheduled time, please allow for time to park, off the pier if necessary.
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  • 1 hour 15 minutes
  • Free Cancellation
From
US$49.00
From
US$49.00

30 Minute Lake Michigan Speedboat Ride
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30 Minute Lake Michigan Speedboat Ride

star-4
199
Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.
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  • 30 minutes
From
US$39.21
From
US$39.21

Bike Tour of Chicago's Lakefront Neighborhoods

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
174
Pedal past the lakefront neighborhoods of Chicago's North Side on this bike tour of the Windy City. Follow a local guide along quiet streets, city parks and scenic beaches, starting at Lake Shore Drive and continuing along Rush Street and the Magnificent Mile. Catch a glimpse of the Playboy Mansion, Oprah’s penthouse and the Victorian houses of Old Town. Select from several departure times in the morning or afternoon.
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  • 3 hours
  • Free Cancellation
From
US$54.99
From
US$54.99

Chicago's Ultimate City Bike Tour
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Chicago's Ultimate City Bike Tour

star-5
92
Explore Chicago’s most iconic sites on a bike tour that explores Museum Campus, parks, and monuments. Follow your guide along the waterfront as you soak up the city skyline and enjoy the breeze along the easy-going route. Circle the Buckingham Fountain while you learn the history of the city’s public art, parks and museums, and capture unforgettable images of the Windy City.
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  • 3 hours
  • Free Cancellation
From
US$54.99
From
US$54.99

Chicago Urban Adventure River and Lake Cruise

Chicago Urban Adventure River and Lake Cruise

star-4.5
193
See the the Second City from the water with a sightseeing cruise along the Chicago River and the Lake Michigan shoreline. Take in towering skyscrapers and spot the gargoyles that live on to of the city’s historic buildings. Hear stories about the city’s history and culture as you pass Chicago landmarks, museums and iconic buildings. Capture unforgettable images of the city skyline from Lake Michigan, and get a unique look at Chicago that’s perfect for all ages.
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  • 1 hour 30 minutes
  • Free Cancellation
From
US$42.00
From
US$42.00

Helicopter Tour - Downtown Chicago

Helicopter Tour - Downtown Chicago

star-4.5
24
The only tour provider near downtown! Unlike other tours, ours is flown in a spacious, turbine-engine helicopter. We will never 'up-sell' clients upon arrival, and our pilots are extremely professional and fun! We believe in taking care of the customer first, and safety is at the heart of all we do. If you are visiting Chicago, this tour is the perfect way to see the city from a new view in a way that will create life-long memories!
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  • 15 to 18 minutes
  • Free Cancellation
From
US$239.00
From
US$239.00

Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour
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Bikes, Bites, and Brews: Chicago's Signature Dishes Bike Tour

star-5
431
Chicago dogs, deep-dish pizza, cupcakes and craft beer are all sampled on this half-day bike tour through the Windy City. Cover about 13 miles (21 km), following an informative guide at a moderate pace through Chicago neighborhoods. On the day tour, ride through Wrigleyville, Old Town, Lincoln Park, and Gold Coast. On the night tour, visit Gold Coast, Chicago’s Riverwalk, Millennium Park, Buckingham Fountain and Chicago’s Lakefront trail. Stop along the way at a popular downtown bakery, pizza shop, hot dog stand and two breweries for a taste of local flavors.
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  • 4 hours
  • Free Cancellation
From
US$89.99
From
US$89.99

Chicago CityPASS

Chicago CityPASS

star-4.5
380
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 Shedd Aquarium, Skydeck Chicago, and the Field Museum plus your choice of admission to 3 of the following attractions: Adler Planetarium, Art Institute of Chicago, Museum of Science and Industry, Chicago, and the 360 CHICAGO Observation Deck. Also enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers. Attractions may be required to verify proof of full COVID-19 vaccination (14 days past final vaccine dose) before allowing entry. Please review attraction requirements before visiting Chicago.
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  • 9 days
From
US$114.00
From
US$114.00

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

Chicago's Lake Michigan Downtown Kayak Rental at Ohio Street Beach

star-5
1
Paddle the calm, clean and turquoise waters of Lake Michigan at your own pace. Kayak the lakefront scenery in downtown Chicago on your own personal kayak, taking in the city skyline and lake views. Pull off at a nearby beachfront and enjoy time on the sand before paddling further. Rentals Available for: 1 hour Single and Tandem Kayaks Available Must be 18+ to rent kayak. Ages 13+ can ride kayak alone if adult (18+) guardian rents the equipment. Tandem kayak is suitable for Ages 4+ as long as with adult (18+) guardian. Beginner kayakers are encouraged to paddle a tandem kayak with a more experienced partner.
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  • 1 hour
  • Free Cancellation
From
US$49.99
per group
From
US$49.99
per group

Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate
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Chicago-Lincoln Park Indoor Skydiving with 2 Flights & Personalized Certificate

star-4.5
46
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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  • 1 hour 15 minutes
From
US$98.09
From
US$98.09

Chicago River Tiki Bar Cruise from Chicago Riverwalk

Chicago River Tiki Bar Cruise from Chicago Riverwalk

star-4
64
Chicago is well known for its architecture and many visitors admire the buildings on a cruise along the Chicago River. Take your river cruise to the next level aboard a floating tiki bar that allows you to take in all the sights with a drink in hand. Your captain also enhances the atmosphere with island tunes as you enjoy your leisurely sail.
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  • 1 hour 15 minutes
  • Free Cancellation
From
US$30.00
From
US$30.00

Chicago Premier Dinner Cruise on Lake Michigan

Chicago Premier Dinner Cruise on Lake Michigan

star-3.5
217
Take a gourmet dinner cruise on a high-end luxury yacht with the stunning skyline of Chicago serving as your backdrop. Climb aboard your recently renovated vessel, featuring a sumptuously-appointed rooftop lounge and stylish interior design, for your cruise along Lake Michigan. Then sit down for a 3-course dinner, informed by some of the world’s top celebrity chefs and composed of fresh ingredients cooked right on-board. After dinner, enjoy coffee and tea, captivating views of Chicago landmarks like the Willis (formerly Sears) Tower and Navy Pier, plus musical entertainment provided by the onboard DJ.
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  • 2 hours 30 minutes
From
US$180.18
From
US$180.18

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