Top Illinois Extreme Sports

Marvel at Chicago's iconic architecture and lakefront from a unique perspective with this 30-minute immersive ride. With drone footage, helicopter-mounted cameras, and other custom media, Flyover Chicago creates the sensation of flying above and through the city to take in its highlights from above. Get up close to details atop the highest skyscrapers and learn about Chicago's history and cityscape during the ride.

Experience the thrill of skydiving, without jumping out of a plane, in a vertical wind tunnel.  Offered throughout the day, you can easily find a time slot that works for you. After small-group training, enjoy two solo sessions in the tunnel during which you float atop wind speeds as fast as 175 mph (282 kph). Feel secure with a guide giving you one-on-one coaching during each 60-second session.

Experience the adrenaline rush of skydiving without jumping out of a plane at iFly Chicago-Rosemont. With start times available throughout the day, you can easily find a session that fits 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.

One of a kind experience you can only find in Chicago. Motorized paddle boards take the stress out of paddling. LED-lights make the boards illuminate the water providing a personal light show.

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 Starved Rock’s canyons, bluffs and seasonal waterfalls on this 3-mile (round trip) guided hike. Listen as the guide tells stories of how Starved Rock got its name along with other legends of the area. Break for lunch at the halfway point. Lunch includes your choice of turkey, ham or veggie wrap, snacks and bottled water. Please wear appropriate clothing and footwear. Hike will vary upon group skill and trail conditions. *Boxed lunch and souvenir drawstring backpack included. Online bookings are subject to additional fees.

This tour offers a personalized and stress-free way to experience Chicago, combining comfortable transportation with local insights and flexible stops. Guests enjoy a private ride through iconic neighborhoods and landmarks while learning about the city’s history, culture, and architecture at their own pace. Ideal for airport transfers, short stays, and first-time visitors seeking a relaxed yet memorable city experience

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller Brewery with exclusive behind-the-scenes access and tastings. With comfortable transport, expert local insights, and a friendly group atmosphere, this all-inclusive adventure is perfect for curious travelers. Book now for a memorable escape to Milwaukee's culture and flavors!

Meet your expert knowledge guide in your hotel lobby and depart in a private, air-conditioned vehicle to the Giza Plateau. The tour begins by exploring the oldest of the Seven Wonders of the Ancient World. You will visit the Pyramid of Cheops (The Great Pyramid of Giza), the largest pyramid in the world. Continue your tour with visits to the Pyramids of Chephren and Mykerinos. Learn the architectural significance and fascinating history of these magnificent structures. You will take some unforgettable photos in the panoramic view area where you will have an optional for a camel ride for 30 minutes to the six pyramids panorama. While on the Giza Plateau, you will see The Great Sphinx of Giza and learn about the mystery of one of the oldest and largest sculptures in the world. You will have an hour of Quad bike ride to places around the pyramids you can't reach by the traditional transportation to have some unforgettable photos.

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel through the Great Lakes region. Discover the island's unique features, where cars are absent, allowing horse-drawn carriages to roam freely among Victorian architecture and beautiful scenery. Enjoy iconic sites like Fort Mackinac and Arch Rock while wandering through quaint downtown shops and savoring famous fudge. This tour is designed for families, couples, and solo travelers looking for a serene getaway filled with natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation

Discover the charm of Mackinac Island on a delightful journey from Chicago, blending history, culture, and stunning landscapes. Without cars, the island embraces a serene atmosphere where horse-drawn carriages navigate past Victorian architecture and picturesque views. Visit iconic sites such as Fort Mackinac and Arch Rock, explore quaint downtown shops, and indulge in the island's famous fudge. This tour is perfect for families, couples, and solo travelers looking for a relaxing getaway immersed in natural beauty and cultural richness. - Scenic travel through the picturesque Great Lakes region - Discover Mackinac Island's charm without car traffic - Visit Fort Mackinac, Arch Rock, and local boutiques - Ideal for families, couples, and solo adventurers seeking relaxation

Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for date nights, anniversaries, and memorable celebrations. Aboard the Vagabond, a Beneteau Oceanis 393 yacht, guests can unwind, capture picturesque moments, and savor their favorite BYOB drinks and snacks against the backdrop of golden-hour light. With a dedicated captain overseeing your journey, relish a tranquil escape just minutes from the bustling city.

Explore the charming towns of Dubuque and Galena on this enriching day trip from Chicago. Begin your journey along the scenic Mississippi River in Dubuque, where you can enjoy free time to stroll, have lunch, or even take a cable car ride for breathtaking views. Continue to Galena, a beautifully preserved historic town where 80% of the buildings are listed on the National Register of Historic Places. Here, you’ll visit the Ulysses S. Grant Home and take in the serene beauty of Grant Park. With a total travel distance of 325 km from Chicago, this tour offers the perfect blend of history, scenery, and relaxation before heading back to the city.