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Top Chicago Outdoor Activities

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We’re committed to helping you feel confident as you get back out there. Check out our flexible cancellation policies and learn what steps operators are taking to keep you safe. As conditions evolve, check local regulations for the latest information.

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62 Chicago Outdoor Activities | All Chicago Tours

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Chicago River Kayak TourKayaking

Chicago River Kayak Tour

star-4.5
Set your paddle into the Chicago River on a leisurely 2.5-hour kayak tour past the skyscrapers of downtown Chicago. Both novice and experienced kayakers will be at ease on this excursion past sights such as the Civic Opera Building and the Marina City Towers. Hear fascinating tales of the Windy City as you gaze at a stunning architectural landscape from the water, just how the original Chicago natives originally navigated the area!
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  • 2 hours 30 minutes
  • Free Cancellation
From
US$66.67
From
US$66.67

30 Minute Lake Michigan Speedboat RideJet Boating

30 Minute Lake Michigan Speedboat Ride

star-4.5
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
  • Free Cancellation
  • Taking safety measures
From
US$33.58
From
US$33.58
Taking safety measures

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

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

star-5
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
  • Taking safety measures
From
US$76.25
From
US$76.25
Taking safety measures

Chicago Architectural River CruiseDay Cruises

Chicago Architectural River Cruise

star-4.5
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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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$49.28
From
US$49.28
Taking safety measures

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)Private and Luxury

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

star-5
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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  • 45 minutes
  • Free Cancellation
  • Taking safety measures
From
US$598.67
per group
From
US$598.67
per group
Taking safety measures

Chicago River Ghosts and Gangsters Kayak TourKayaking

Chicago River Ghosts and Gangsters Kayak Tour

star-5
Paddle through Chicago’s wild past on a 2.5-hour small group kayak tour on a river that curls through the heart of the Windy City. Learn to navigate your boat and try out paddling techniques, then get ready to navigate the illuminated downtown section of the river. Hear stories of gangsters and their ghosts as you explore the city’s underbelly alongside your guide, and get a glimpse of the city’s gritty past as you travel along riverbanks lined with iconic skyscrapers and historic sites.
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  • 2 hours 30 minutes
  • Free Cancellation
From
US$66.67
From
US$66.67

2 hour Guided Segway TourHistorical Tours

2 hour Guided Segway Tour

star-5
2 hours of being a kid again!!! Take a Segway tour with us and discover how beautiful Chicago truly is. Ride through some of Chicago's most popular destinations with an experienced guide. We will glide through scenic and historic downtown Chicago and explore the beautiful Grant Park, around the Buckingham Fountain, near the Museum Campus and near the lakefront. Or take our Riverwalk tour to explore the Chicago River to view Navy Pier and famous Chicago bridges, traveling up historic Michigan Avenue and passing by Millennium Park. No matter which tour you choose, it will be a memory lasting a lifetime!
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  • 2 hours
  • Free Cancellation
From
US$65.00
From
US$65.00

Chicago's Ultimate City Bike TourMountain Bike Tours

Chicago's Ultimate City Bike Tour

star-5
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
  • Taking safety measures
From
US$45.99
From
US$45.99
Taking safety measures

Chicago Architecture Center River Cruise aboard Chicago's First LadyDay Cruises

Chicago Architecture Center River Cruise aboard Chicago's First Lady

star-5
The Chicago Architecture Center River Cruise aboard Chicago's First Lady has long been the gold standard among all Chicago tour experiences, and is the only Chicago architecture boat tour led by highly trained expert docents. On this 90-minute cruise, you will enjoy an overview of historic and modern architectural styles including stories about the people who designed and built Chicago. No visit to Chicago is complete without experiencing this award winning tour, so accept no substitutes.
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  • 1 hour 30 minutes
  • Taking safety measures
From
US$53.25
From
US$53.25
Taking safety measures

The Escape Game Chicago: Epic 60-Minute AdventuresEscape the Room

The Escape Game Chicago: Epic 60-Minute Adventures

star-4
Located in River North, these adventures offer a one-of-a-kind premium experience. Follow clues and solve puzzles to complete your mission together. You might escape...You WILL have fun! Choose to play one of five uniquely immersive games: - Gold Rush: Find hidden gold in the California hills! - Prison Break: Complete a daring escape from the evil warden! - Special Ops: Mysterious Market: Uncover the truth as a secret agent! - The Heist: Recover a stolen masterpiece from an art thief! - Mission: Mars: Launch your spaceship from the Red Planet!
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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$39.23
From
US$39.23
Taking safety measures

Private Pontoon Boat Rental with Pizza IncludedBoat Rentals

Private Pontoon Boat Rental with Pizza Included

star-4.5
Set your own course on this private self-guided cruise along the Chicago River. You're the captain for your group of just eight people, steering the boat wherever you like and getting epic views of the towering buildings along the river. When the munchies hit, grill up the provided pizza on the boat's barbecue and dig in.
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  • 2 hours
  • Free Cancellation
From
US$297.60
per group
From
US$297.60
per group

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

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

star-5
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 the Chicago neighborhoods of Wrigleyville, the Gold Coast, Old Town, Lakeview and Lincoln Park. 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
  • Taking safety measures
From
US$79.99
From
US$79.99
Taking safety measures

Chicago Loop Walking TourPrivate and Luxury

Chicago Loop Walking Tour

star-5
Step into the heart of Chicago with this 2-hour walking tour of the Loop. You’ll meet your local guide at the Chicago Cultural Center and make your way through the city’s downtown. Stop to check out the elevated “L” train, buildings by Burnham and Sullivan, busy commercial centers and lesser-known quiet corners of this vibrant area. You’ll come away with a deeper sense of Chicago’s rich history and architecture.
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  • 2 hours
  • Free Cancellation
From
US$40.00
From
US$40.00

Private Chicago City Sights Helicopter TourPrivate Sightseeing Tours

Private Chicago City Sights Helicopter Tour

star-4.5
You and a guest will soar above Chicago’s skyscapers, shoreline and iconic sights on a private, 15-minute helicopter tour of the city. Communicate with your personal pilot through a two-way headset, and personalize your flight to your interests. Capture extraordinary aerial images of the city scape as you fly past Lincoln Park and Lake Michigan, then spot Willis Tower, the John Hancock Building and the gleaming Trump Tower. Bank high above Millennium Park and enjoy views of the Windy City from the comfort of a climate-controlled private helicopter. Tour route is subject to change.
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  • 30 minutes
  • Free Cancellation
From
US$408.00
From
US$408.00

Chicago CityPASSAttraction Tickets

Chicago CityPASS

star-4.5
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 as well as a choice of the Art Institute of Chicago or Adler Planetarium, and Museum of Science and Industry or 360 Chicago (John Hancock Observatory). Plus enjoy a wealth of useful Chicago tips and savings at a variety of other venues and retailers.
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  • 9 days
  • Free Cancellation
From
US$109.00
From
US$109.00

Chicago Odyssey Lake Michigan Lunch CruiseDay Cruises

Chicago Odyssey Lake Michigan Lunch Cruise

star-4
Board a luxurious yacht at Navy Pier for a 2-hour lunch cruise along Chicago’s scenic shoreline. Enjoy a three-course gourmet meal as you take in views of the Windy City from a climate-controlled observation deck, then sip coffee or tea while the yacht’s onboard DJ spins a leisurely afternoon playlist.
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  • 2 hours
  • Taking safety measures
From
US$88.26
From
US$88.26
Taking safety measures

Aqua Water Trike RentalsBoat Rentals

Aqua Water Trike Rentals

star-1
Cruise around Lake Michigan and enjoy spectacular views of Chicago on an Aqua Water Trike. This 30-minute rental lets you explore at your own pace and experience the city from the water. There is space for two people per bike and no experience is required—simple hop aboard and pedal your way around the lake.
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  • 30 minutes
  • Taking safety measures
From
US$13.50
From
US$13.50
Taking safety measures

Lake Michigan Sightseeing CruiseDay Cruises

Lake Michigan Sightseeing Cruise

star-4.5
Take in superlative-worthy views of the beautiful Chicago lakefront and its many landmarks during this 40-minute Lake Michigan sightseeing boat cruise. Climb aboard your vessel for a laid-back ride, enjoying panoramic views of the Windy City's iconic 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
  • Taking safety measures
From
US$25.07
From
US$25.07
Taking safety measures

Chicago Lake and River Architecture TourDay Cruises

Chicago Lake and River Architecture Tour

star-4.5
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
  • Taking safety measures
From
US$39.00
From
US$39.00
Taking safety measures

Chicago Architecture River CruiseDay Cruises

SPECIAL OFFER

Chicago Architecture River Cruise

star-5
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 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$35.49
US$40.33
US$4.84 savings
From
US$35.49
US$40.33
US$4.84 savings
Taking safety measures

Private Sunset Sail on Lake Michigan with Breathtaking Views of ChicagoDay Cruises

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

star-5
Soak up the views of Lake Michigan and the Chicago skyline with a 2-hour sailing tour. This private charter is completely customizable, giving you the chance to choose your music, route, and up to 5 additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$427.28
per group
From
US$427.28
per group
Taking safety measures

90-min Chicago River Architecture TourDay Cruises

90-min Chicago River Architecture Tour

star-4.5
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
  • Taking safety measures
From
US$39.00
From
US$39.00
Taking safety measures

Chicago Skyline Sailboat CruiseDay Cruises

Chicago Skyline Sailboat Cruise

star-4.5
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.
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  • 1 hour 15 minutes
  • Free Cancellation
  • Taking safety measures
From
US$35.84
From
US$35.84
Taking safety measures

Chicago River Boat Architecture TourDay Cruises

Chicago River Boat Architecture Tour

star-5
Welcome to Chicago River Boat Architecture Tours! We’re proud to present you with an in-depth, expert architectural-based river boat tour that delves into one of the most remarkable American cities today. Known for unique, daring, and historical architectural pursuits, it’s hard to cover all of the design and building treasures that make up the Windy City today. If you’re ready to learning more about the designs, people, and innovations behind these creations, throw on your captains hat and get ready to cruise along the Chicago River and see what architects from around the world travel to see in Chicago. Tour departures from 465 N. McClurg Ct.
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  • 1 hour 30 minutes
  • Free Cancellation
  • Taking safety measures
From
US$49.28
From
US$49.28
Taking safety measures

Frequently Asked Questions

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
Q:
What are the best Outdoor Activities in Chicago?
Q:
What Outdoor Activities in Chicago are 1 hour or less?
Q:
What tours in Chicago are taking additional safety precautions?
Q:
What tours in Chicago are good for avoiding crowds?

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