Top Illinois Adventure Tours

Experience a colorful side of Chicago history with this gangsters and ghosts tour. With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.

Explore Chicago's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, and John Dillinger, among other thugs hung out. A history-savvy guide introduces you to some of the most storied locations of Chicago’s criminal past, including Holy Name Cathedral, Biography Theatre, and the site of the bloody St. Valentine’s Day Massacre. You'll be able to get out and pose for pictures in front of a historic courthouse, among other infamous sites.

Enjoy an active and entertaining way to explore Chicago’s highlights with this small-group Segway tour. Meet your guide at a convenient location in downtown Chicago, get acquainted with your Segway before setting off, and then hit the road. You’ll discover top Windy City highlights, including Millennium Park, the Buckingham Fountain, the Museum Campus, and more, all while learning about the city’s history and insider facts from your guide.

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.

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.

Leave behind the stuffy, slow-moving tour groups and explore Chicago’s Millennium Park on your own—but with a guide in your pocket. Using just your smartphone, pausing as you like, you’ll learn all about “The Bean,” Lurie Garden, Crown Fountain, and so much more. With your GPS cuing your audio experience, this tour is all about going at your pace, at your style, and on your time.

Dog Friendly! Come see the beautiful Starved Rock Area as we wander through towering St. Peters sandstone bluffs with Bald Eagles soaring overhead. Great American Pelicans populate this area along with blue herons, turtles and more. Our tour guides will educate and entertain you as you paddle through an American lotus flower field on the water. Your 2 hour adventure begins with a land based lesson and safety briefing and then we venture out on the water for a trip you will never forget. Our tandem kayaks hold up to 3 ppl if 3rd is under 70 lbs also we allow dogs on our tours now in tandem kayaks! a dog up to 40lbs can ride as a 3rd passenger for a fee and any size dog can ride as a 2nd passenger for a fee

Enjoy a new perspective on Chicago’s iconic skyline—and a high-octane sightseeing experience—on this small-group adventure boat tour. Choose from a range of departure times, meet your guide right at the waterfront, and hop aboard your high-speed vessel. Then, zip off: in between admiring highlights like the Museum Campus, Navy Pier, and Millennium Park, you’ll learn more about Chicago’s history.

As one of the largest islands in the Caribbean, Jamaica packs a punch in the natural beauty stakes. On this trip, you'll get to visit two of her knockout spots in just one day. Make a Tarzan-like rope swing splash into the exotic Blue Hole springs before making the trek up Dunn's River Falls. We kick off with a drive through lush green landscapes to a true Instagram hotspot – the Blue Hole. Explore a nearby cave, swing like Tarzan into one of three pools, and enjoy a cool swim in this mineral spring. After a delicious local lunch, we'll head to Dunn's River Falls – one of the stars of the Bond film Dr. No. Admire the 180-meter-high staircase of rock with water thundering down it and you can follow your guide to the top. Luckily, it's an easy scramble to the summit and anyone from toddlers to seniors, can have a go. But, if you don't fancy the climb, you can follow the trails on either side or stay at the base relaxing in the tropical surroundings. Thrill-seekers will love this one.

Our very unique, immersive adventures are the only ones of their kind. We, unlike other companies, provide your very own remote, interactive, live host to assist and encourage you along through your phone. We are an Austin, TX-based global custom event design company offering scavenger hunts and other events in 300+ cities in North America and beyond. Our specially hand-crafted adventures are equal parts tour, creative challenge, detective hunt, and social experiment! Guests get to discover in an alternate reality our favorite hidden gems off the beaten trail and creatively interpret fun art, history, and culture clues - for points! They get to enjoy fame and glory while appearing on our website’s international leaderboard, no matter what their score. They get to essentially race other teams in other cities, even if they don’t have competitors who have signed up in their city that day. Get ready to discover unusual oddities, laugh out loud, and make the experience your own!

Experience Chicago's Magnificent Fireworks from the Water with Navy Seal Adventure Boat Are you ready for an unforgettable evening of breathtaking views and heart-pounding excitement? Look no further than our Navy Seal Adventure Boat, where we bring you front-row seats to the most spectacular firework show in Chicago! Get ready to embark on a journey like no other, as we take you on an adrenaline-fueled adventure that will leave you in awe. The Ultimate Waterfront Spectacle Situated on the glistening waters of Lake Michigan, our Navy Seal Adventure Boat offers an unparalleled vantage point to witness the city's iconic firework extravaganza. As the sun dips below the horizon, the anticipation builds, and our expert crew navigates the boat to prime position for the best views of the show. Feel the thrill as the sky comes alive with a mesmerizing kaleidoscope of colors, perfectly synchronized to an enchanting symphony of music.