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.

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.

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!

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.

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.

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.

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.

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).

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.

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.

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.

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.

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.

Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.

Glamorous professional photo shoot in unique Chicago locations. The Photo Experience will create amazing photo memories from your holiday. You will be able to see undiscovered locations, and get the best photo story from your Chicago visit. We can tailor each photo shoot to meet your requirements. Our Photoshoots are ideal for any Tourists - Solo Traveler - Couples - Groups - Hen/Bachelorette & Stag/Bachelor Parties - Families - Secret proposal/Engagement - Honeymoon - Experienced Influencers and Models - New Influencers and Models What's Included: A Private online viewing gallery - 1 hour = 20 professionally edited photos* - 2 hours = 30 professionally edited photos* - 3 hours = 40 professionally edited photos* - 4 hours = 50 professionally edited photos* * same set of images - A unique location professional shoot experience for your holiday - DELIVERY - Up to 14 days after photoshoot. What's Excluded: - Transportation - Entry fees

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.

TEG Unlocked is an interactive virtual escape game that you can play from anywhere. The engaging game has two different missions to choose from and can be played on your own or with a group of friends. You are granted unlimited time to unravel the puzzles and solve clues, with hints accessible during each adventure so you don’t have to worry about getting stuck.

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.

Named for the cable car turnarounds and the prominent elevated railway that encircled the area at the end of the 19th century, the Loop is Chicago's commercial and cultural core. On today's epic scavenger hunt of Chicago, you'll uncover the area's best sights and rich history. Along the way, you'll visit Cloud Gate, Art Institute of Chicago, and the Federal Reserve Bank of Chicago. It's time to strap on those walking shoes, round up some friends and book your Chicago Loop scavenger hunt today! What You'll See: Tiffany Dome, The Bean, Crown Fountain, Art Institute of Chicago

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.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.

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.

Let’s Roam is the #1 app-led scavenger hunt company. Walk to all the best landmarks and hidden gems, answering trivia questions and solving challenges. Work with your team or compete against them, as you learn new facts and create memorable experiences. Let’s Roam Scavenger Hunts are great as an everyday activity, or for bachelorette parties, birthday parties, corporate team building events and more! Each player chooses an interactive role, with challenges varying by person.