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Top Chicago Outdoor Activities

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62 Chicago Outdoor Activities | All Chicago Tours

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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 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

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

Spirit of Chicago Sunset Dinner Cruise with BuffetHalf-day Tours

Spirit of Chicago Sunset Dinner Cruise with Buffet

star-4.5
Make your evening in Chicago one to remember with this luxury sunset cruise featuring dinner, sightseeing and dancing along the shores of Lake Michigan. Feast your eyes on incredible views of iconic Windy City sights like Navy Pier, the Willis (Sears) Tower, Buckingham Fountain and Soldier Field, then fill your belly with a bountiful all-you-can-eat buffet. Continue the celebration with a live DJ who will mix up a selection of dance favorites.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$112,74
From
US$112,74
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

45-min Chicago River Architecture TourDay Cruises

45-min Chicago River Architecture Tour

star-4.5
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
  • Taking safety measures
From
US$23,00
From
US$23,00
Taking safety measures

Chicago Odyssey Dinner CruiseDay Cruises

Chicago Odyssey Dinner Cruise

star-4
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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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
US$108,66
From
US$108,66
Taking safety measures

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-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
  • Free Cancellation
  • Taking safety measures
From
US$76,25
From
US$76,25
Taking safety measures

Spirit of Chicago Lunch Cruise with BuffetDay Cruises

Spirit of Chicago Lunch Cruise with Buffet

star-4.5
Perfect for families, groups, and corporate outings, the Spirit of Chicago lunch cruise lets you kick back and enjoy a great meal while taking in the sights of Chicago's most famed landmarks. See and photograph the dramatic city skyline, Navy Pier, Soldier Field, and Shedd Aquarium. The cruise includes a delicious buffet lunch with salads, entrees, desserts, and unlimited nonalcoholic beverages. There's also a DJ, games, and a dance floor to keep your group entertained.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
US$74,66
From
US$74,66
Taking safety measures

Chicago City Sights Helicopter TourHelicopter Tours

Chicago City Sights Helicopter Tour

star-5
Soar above the incredible skyline of Chicago during this 15-minute helicopter flight above the Windy City. Climb aboard your high-tech helicopter for a ride like no other, admiring views of Lake Michigan plus iconic city sights like Millennium Park, Lincoln Park, Navy Pier, the Shedd Aquarium and the Willis Tower. Along the way you'll hear informative details about the various landmarks from your pilot, who will provide commentary during the flight. Tour route is subject to change.
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  • 30 minutes
  • Free Cancellation
From
US$179,00
From
US$179,00

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

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'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

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

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 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

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

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

Odyssey Chicago River Dinner CruiseDay Cruises

Odyssey Chicago River Dinner Cruise

star-5
Cruise down the Chicago River in style during this 3-hour dinner cruise aboard the Odyssey. Watch the beautiful city and its architecture pass by through the ship’s panoramic windows. Then sit down to delicious 3-course meal accompanied by DJ entertainment to set the mood for your journey. A full-service bar complete with microbrews, creative cocktails, and a wine list is also available for purchase.
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  • 3 hours
  • Taking safety measures
From
US$169,86
From
US$169,86
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods Mountain Bike Tours

Bike Tour of Chicago's Lakefront Neighborhoods

star-5
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
  • Taking safety measures
From
US$46,99
From
US$46,99
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

Private Lake Michigan Sailing Charter and Sightseeing Tour of ChicagoDay Cruises

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

star-5
If you’ve ever dreamed of sailing away on your own private sailboat, this is the perfect excursion for you. You and up to five other invited guests will have the exclusive use of a sailboat, complete with captain and crew for the duration of your tour. Sail on Lake Michigan and enjoy the sights of Chicago’s striking skyline. If you want, you could even take a turn at the helm.
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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

Chicago Lakeside Architecture TourSailing

Chicago Lakeside Architecture Tour

star-4.5
Get views of Chicago's famous architecture from the deck of a boat during this sailing excursion. Learn about the people, plans, and persistence that shaped Chicago's architecture along the shoreline. Hear about the city's historical maritime roots to modern science and technology through your guide's commentary while taking advantage of great photo ops. Choose between an afternoon or early evening departure and relax as you enjoy the sights. 
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  • 1 hour 15 minutes
From
US$40,46
From
US$40,46

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