People head to the Windy City for more than just pizza , as they should. In the summer you can claim part of the Lake Michigan shoreline, and when temperatures dip Millennium Park opens up an ice skating rink. From fine dining to world-class shopping , there are plenty of fun things to do in Chicago, Illinois. Of course, the Chicago art and culture scene is also quite the draw, bringing in all types of travelers from around the globe. You’re bound to leave Chicago with a full stomach and lots to talk about.
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Chicago (and vicinity), Illinois, United States of America
Adventures in Chicago
Chicago Tours, Sightseeing and Attractions
Chicago Adventures Deals
- All Activities (118)
- Adventures (5)
- Air, Balloon & Helicopter Tours (5)
- Airport Shuttles & Limos (25)
- Attractions (21)
- Culinary Experiences (34)
- Day Cruises & Water Activities (7)
- Events & Shows (3)
- Land Adventures (38)
- Restaurants & Nightlife (34)
- Spas & Beauty (1)
- Sports (3)
- Tickets & Passes (5)
- Tours & Sightseeing (70)

Embark on an interactive tour of Chicago and discover the city while using hints and completing unique challenges. See landmarks and historical locations as you solve clues on your smartphone that lead you on a memorable tour of the Windy... City.
In Chicago, filled with rich history and beautiful public art, begin your scavenger hunt and stroll along the riverside through 4 different, distinctively beautiful districts boasting their own unique style and historical sites. Using your smartphone, tablet, or other mobile device, follow clues and solve questions along the way.
Your journey will take you to the Hard Rock Hotel, the Art Institute of Chicago, and Cloud Gate, nicknamed the Bean due to its bean-like shape. Completed in 2006 and made of 168 stainless steel plates, this work of modern art in Millennium Park vividly reflects and distorts the city's skyline and makes an excellent photo spot.
Complete challenges, get hints, and earn points as you meander through the city. Take a step back to the past as you visit the Palmer House and learn how it was destroyed during the Great Chicago Fire and then rebuilt as a stunning work of modern architecture. After learning your way around this fascinating city, wrap up your quest with a sense of confidence and accomplishment. Read More close
In Chicago, filled with rich history and beautiful public art, begin your scavenger hunt and stroll along the riverside through 4 different, distinctively beautiful districts boasting their own unique style and historical sites. Using your smartphone, tablet, or other mobile device, follow clues and solve questions along the way.
Your journey will take you to the Hard Rock Hotel, the Art Institute of Chicago, and Cloud Gate, nicknamed the Bean due to its bean-like shape. Completed in 2006 and made of 168 stainless steel plates, this work of modern art in Millennium Park vividly reflects and distorts the city's skyline and makes an excellent photo spot.
Complete challenges, get hints, and earn points as you meander through the city. Take a step back to the past as you visit the Palmer House and learn how it was destroyed during the Great Chicago Fire and then rebuilt as a stunning work of modern architecture. After learning your way around this fascinating city, wrap up your quest with a sense of confidence and accomplishment. Read More close
$38
per Group

Experience the Windy City from above with a dazzling daytime helicopter tour—the ultimate way to take in the city's beauty. Learn about the history of the Chicago and see some of its most famous landmarks as you soar over the... city skyline.
Check in at the meeting location with plenty of time to spare. You then have the opportunity to learn some of Chicago’s rich history as you explore the exhibits of the Customer Experience Center. As the rotors whir to life, board your state-of-the-art helicopter and lift off.
Relax, take photos, and enjoy the sights as your expert pilot narrates your journey. Gaze out at unparalleled views of the city as you fly over gorgeous Lake Michigan and other well-known landmarks. Marvel at the 110-story Willis Tower (often referred to as Sears Tower)—North America's tallest building—and Wrigley Field, home of the Chicago Cubs. Once you touch back down, receive a high-resolution digital copy of your photograph in front of the helicopter. Read More close
Check in at the meeting location with plenty of time to spare. You then have the opportunity to learn some of Chicago’s rich history as you explore the exhibits of the Customer Experience Center. As the rotors whir to life, board your state-of-the-art helicopter and lift off.
Relax, take photos, and enjoy the sights as your expert pilot narrates your journey. Gaze out at unparalleled views of the city as you fly over gorgeous Lake Michigan and other well-known landmarks. Marvel at the 110-story Willis Tower (often referred to as Sears Tower)—North America's tallest building—and Wrigley Field, home of the Chicago Cubs. Once you touch back down, receive a high-resolution digital copy of your photograph in front of the helicopter. Read More close
$128
per Traveler

Watch the door close and the lock turn as you get trapped in a room with only your wits to rely on. On this brain-tickling excursion, gather friends to help you tackle challenging riddles, puzzles, and clues that lead you... to uncover the only way to escape themed rooms decorated to frighten and entice.
Meet at the escape room and join your group, made up of family, friends, and possibly some like-minded sleuths. Go over the rules and grab any clues you might need to get started, then head inside and let staff lock you inside before starting the clock.
Whether you're trying to get out of a room on the verge of being invaded by zombies or working to solve a magician's most challenging riddles, beat the clock by finding tantalizing clues and solving complex logic games to find the key and escape. Read More close
Meet at the escape room and join your group, made up of family, friends, and possibly some like-minded sleuths. Go over the rules and grab any clues you might need to get started, then head inside and let staff lock you inside before starting the clock.
Whether you're trying to get out of a room on the verge of being invaded by zombies or working to solve a magician's most challenging riddles, beat the clock by finding tantalizing clues and solving complex logic games to find the key and escape. Read More close
Categories: Adventures
1 hour
$40
per Traveler

Experience all the plummeting, free fall, and soaring sensations of skydiving without ever getting on a plane. This indoor skydiving experience puts you in a vertical wind tunnel, so you can float weightlessly in space for an unforgettable adrenaline rush... in totally safe surroundings.
Arrive at iFLY and get geared up, stepping into your flight suit, strapping on your helmet, and adjusting your protective goggles to fit. An experienced and accredited instructor leads you in an introductory training session so you can get the most out of your adventure, and then it’s time to step into the flight chamber.
The instructor accompanies you inside so they can offer tips and pointers as you fly, and you’re lifted off your feet as the chamber fills with rushing wind. Hover above the ground, spin through the air, and feel the thrill before touching back down on solid ground, catching your breath, and doing it all over again. Read More close
Arrive at iFLY and get geared up, stepping into your flight suit, strapping on your helmet, and adjusting your protective goggles to fit. An experienced and accredited instructor leads you in an introductory training session so you can get the most out of your adventure, and then it’s time to step into the flight chamber.
The instructor accompanies you inside so they can offer tips and pointers as you fly, and you’re lifted off your feet as the chamber fills with rushing wind. Hover above the ground, spin through the air, and feel the thrill before touching back down on solid ground, catching your breath, and doing it all over again. Read More close
$70
per Traveler

Experience all the plummeting, free fall, and soaring sensations of skydiving without ever getting on a plane. This indoor skydiving experience puts you in a vertical wind tunnel, so you can float weightlessly in space for an unforgettable adrenaline rush... in totally safe surroundings.
Arrive at iFLY and get geared up, stepping into your flight suit, strapping on your helmet, and adjusting your protective goggles to fit. An experienced and accredited instructor leads you in an introductory training session so you can get the most out of your adventure, and then it’s time to step into the flight chamber.
The instructor accompanies you inside so they can offer tips and pointers as you fly, and you’re lifted off your feet as the chamber fills with rushing wind. Hover above the ground, spin through the air, and feel the thrill before touching back down on solid ground, catching your breath, and doing it all over again. Read More close
Arrive at iFLY and get geared up, stepping into your flight suit, strapping on your helmet, and adjusting your protective goggles to fit. An experienced and accredited instructor leads you in an introductory training session so you can get the most out of your adventure, and then it’s time to step into the flight chamber.
The instructor accompanies you inside so they can offer tips and pointers as you fly, and you’re lifted off your feet as the chamber fills with rushing wind. Hover above the ground, spin through the air, and feel the thrill before touching back down on solid ground, catching your breath, and doing it all over again. Read More close
$70
per Traveler