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Top Chicago Outdoor Activities

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Tandem Skydiving Experience in Chicago

Tandem Skydiving Experience in Chicago

star-5
Go skydiving in Indiana at a location situated only a 1-hour train ride from Chicago, making it easy to reach without a car. Your instructor provides all necessary equipment and training for your jump, then accompanies you on the tandem skydiving experience from 14,000 feet (4,267 meters). See Lake Michigan and perhaps the Chicago skyline from the air, and purchase video and photos of your jump if you wish.
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  • 3 hours
  • Free Cancellation
  • Taking safety measures
From
$209.00
Price varies by group size
From
$209.00
Price varies by group size
Taking safety measures

Private Sunset Sail on Lake Michigan with Breathtaking Views of Chicago

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
$427.28
per group
From
$427.28
per group
Taking safety measures

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

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
$76.25
From
$76.25
Taking safety measures

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

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
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Private Lake Michigan Sailing Charter and Sightseeing Tour of Chicago

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
$427.28
per group
From
$427.28
per group
Taking safety measures

45 Minute Chicago Helicopter Skyline Tour (for 3 passengers)

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
$622.20
per group
From
$622.20
per group
Taking safety measures

Chicago Tandem Skydive

Chicago Tandem Skydive

star-5
Take your Chicago vacation, literally, to the next level with a tandem skydiving experience in Rochelle. No previous experience is necessary, which makes the aerial excursion perfect for first-timers. Your certified instructor takes care of the technical aspects, so you’re free to enjoy the thrill of skydiving. For an additional cost, you can take home photos and video of your adrenaline fueled adventure.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$199.99
From
$199.99
Taking safety measures

Bike Tour of Chicago's Lakefront Neighborhoods

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
$49.99
From
$49.99
Taking safety measures

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

Chicago-Rosemont Indoor Skydiving with 2 Flights & Personalized Certificate

star-5
Discover the adrenaline rush of skydiving without setting foot on a plane at iFly Chicago-Rosemont. Offered 9am to 10pm, you can easily find a session that fits with 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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  • 1 hour 15 minutes
  • Taking safety measures
From
$76.44
From
$76.44
Taking safety measures

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

Bikes, Bites, and Brews: Chicago's West Side Foodie Ride

star-5
Taste food from around the world on this half-day cycling and tasting tour of Chicago. Follow your biking guide through the Chicago streets, stopping for views of Chicago’s famous architecture as well as bites like Polish pierogis, locally made chocolates, and Mexican tacos.
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  • 4 hours
  • Free Cancellation
  • Taking safety measures
From
$84.99
From
$84.99
Taking safety measures

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

Real Pirates of the Inland Seas: Chicago Pirate-Themed Sailboat Tour

star-4.5
Experience Lake Michigan from a perspective rare to visitors and locals alike on a pirate–themed sailboat tour. Your guides tell true but little–known stories about pirates, battles, and treasure hunts as you cruise past sweeping views of the Chicago skyline. Relax on deck while or join your guides for an interactive experience—the flexibility of the tour makes this a popular choice for families with children.
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  • 1 hour 15 minutes
  • Free Cancellation
From
$40.46
From
$40.46

Chicago Odyssey Lake Michigan Lunch Cruise

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
$88.26
From
$88.26
Taking safety measures

Chicago Odyssey Dinner Cruise

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
$108.66
From
$108.66
Taking safety measures

Spirit of Chicago Lunch Cruise with Buffet

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
$74.66
From
$74.66
Taking safety measures

Chicago's Ultimate City Bike Tour

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
$49.99
From
$49.99
Taking safety measures

Chicago Architecture River Cruise

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
  • Free Cancellation
  • Taking safety measures
From
$38.85
From
$38.85
Taking safety measures

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Learn to Fly a Helicopter: Chicago Helicopter Pilot Intro Flight

Aviation fanatics can take to the skies and try flying an actual helicopter with this Schaumburg flight experience that's perfect for first-timers. You enjoy helpful advice from your instructor before taking the controls on a flight that whisks you past Sears Centre Arena, Woodfield Mall, and Boomers Stadium. With free parking, noise-canceling headphones, and one-on-one attention from the pilot, this beginner-friendly experience is a near-perfect way to try flying for yourself.
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  • 30 minutes
  • Free Cancellation
  • Taking safety measures
From
$189.00
per group
From
$189.00
per group
Taking safety measures

Chicago Odyssey Lake Michigan Brunch Cruise

Chicago Odyssey Lake Michigan Brunch Cruise

star-4
Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.
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  • 2 hours
  • Free Cancellation
  • Taking safety measures
From
$108.66
From
$108.66
Taking safety measures

The Escape Game Chicago: Epic 60-Minute Adventures

The Escape Game Chicago: Epic 60-Minute Adventures

star-5
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
$39.23
From
$39.23
Taking safety measures

Chicago Loop Walking Tour

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
$40.00
From
$40.00

Lake Michigan Sightseeing Cruise

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
$25.07
From
$25.07
Taking safety measures

Aqua Water Trike 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
$13.50
From
$13.50
Taking safety measures

Chicago's Premier Escape Room

Chicago's Premier Escape Room

star-5
Immerse yourself in a fictional adventure at one of Chicago’s premier escape room venues. You have one hour to bust out—work together with your teammates to solve puzzles and decipher clues that lead to freedom. Choose from themes like “The Bank,” “The Bunker,” “The Prison,” and “Zodiac" (additional cost), which can accommodate three to six players.
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  • 1 hour
  • Taking safety measures
From
$43.59
From
$43.59
Taking safety measures

Chicago CityPASS

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
$109.00
From
$109.00

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