Top Chicago Outdoor Activities

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.

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.

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.

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.

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!

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.

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.

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.

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.

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.

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).

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.

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.

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.

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.

The Sunset Cruise departs from the DuSable (Michigan Avenue) Bridge on Wendella's world class tour boats. Enjoy the beautiful City architecture from the best vantage point in Chicago. The vessel will then navigate through the Chicago Lock and out onto Lake Michigan. Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise.

Enjoy admission to more than 26 of Chicago's most popular attractions with the Go Chicago™ Pass. Create your own itinerary and sightsee at your own pace. Save your pass, available as your 'ticket' after purchase, on your mobile device; don't waste time redeeming vouchers. This pass offers something for all members of the family. Take a hop-on hop-off trolley tour or admire the stunning views from SkyDeck Chicago. The Go Chicago™ Pass is available in 1-, 2-, 3-, or 5-day options. Please note: Enjoy the extra flexibility in case your travel plans need to change: All passes are valid for two year from purchase date and only become activated with your first attraction visit. After activation your pass will be valid for 30 days and/or the remaining number of attraction choices purchased.

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.

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.

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.

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.

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.

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.

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.