An Adventure Traveler’s Guide to Chicago

Kayaking on the river through Chicagos Loop is the most unique and adventurous way to see the city
Kayaking on the river through Chicago's Loop is the most unique and adventurous way to see the city | © David Wilson / Flickr
Sarah Ashley

Not all who wander are lost, and not all who travel to Chicago are going to have fun at Navy Pier. Nothing against Navy Pier—it’s just the No. 1 tourist attraction in the city. Adventure seekers cannot simply limit themselves to the traditional Windy City guidebook; they require activities with a little more “oomph” and excitement.

The excursions on this list are sure to please adventurous travelers from around the globe—while still offering up a classic taste of good ole Chicago.

Willis Tower Ledge


© Bari D / Flickr
Fair warning—this spot is not for the faint of heart. For those willing adventurers, this architectural innovation truly offers one of the craziest views in and of Chicago. Sitting at 1,353 feet (412.39 meters) high, The Ledge is a group of glass boxes extending 4.3 feet (1.31 meters) out from the Willis Tower Skydeck. Stand on the glass floor of one of these boxes and look out to see a side of the city you’ve never seen before and can’t get anywhere else. Look down—at your own discretion—to feel like you’re floating 103 floors above the street (which you are).

Each glass panel of The Ledge weighs 1,500 pounds (680.3 kilograms) and combines three layers of glass to create a safe viewing experience for visitors. At 110 stories, the Willis Tower is the eighth tallest building in the world. It’s also the most touristy attraction on this list, for sure. But what daredevil can resist the opportunity to walk on air? For minimal wait times, get there right when the Skydeck opens or after 5 pm.


Natural Feature

© David Wilson / Flickr
Wateriders offers people a chance to see Chicago from another unique perspective—one that could be described as the exact opposite of the Willis Tower Skydeck view. This company leads locals and tourists alike along the Chicago River in kayaks, paddling through the city on exciting and educational tours.

Tens of thousands of people have hopped into colorful kayaks for a river tour since Wateriders got started in 1997. It truly is “Good Green Fun” for the whole family; kayakers of all ages are encouraged to join in, and that includes dogs (yes, dogs are allowed). Choose from an assortment of architecture, history, gangster, sunset, or moonlight tours, all guided by experienced and knowledgeable professionals. Tours range from 1.5 to 2 hours, so get your sunscreen out, toss on a lifejacket, and start paddling.

Trapeze School of New York – Chicago

Fitness Studio, School

© marabuchi / Flickr

The Trapeze School of New York got started in the Big Apple, and it has since expanded to several additional cities, including Chicago. The school offers classes in flying trapeze, trampoline, and acrobatics, to name a few. The goal for each course is to increase students’ awareness of their bodies, minds, and emotions.

The studio has two locations in Chicago (one indoors, one outdoors). The outdoor location is right on Belmont Harbor next to Lake Michigan, offering up beautiful views of the city skyline. Participants can get a sense of what it feels like to fly through the air—safely!—as a way to improve endurance, strength, and awareness. Trapeze classes are offered during the day and in the evening, which adds flexibility to travelers’ schedules. This adventure is an excellent way to take in the beauty of Chicago’s Lakefront Trail and push yourself physically at the same time.

Chicago Water Taxi

Bridge, Train Station

© Bernt Rostad from Oslo, Norway / WikiCommons

Rather than taking an Uber or Lyft around downtown Chicago, why not try a boat? The Chicago Water Taxis ferry tourists and commuters along the Chicago River to various stops and stations for work, travel and play. Operated by Wendella Boats, which also offers guided architecture tours along the Chicago River, the Chicago Water Taxis connect riders to seven areas in the city.

On Wednesday and Saturday nights, water taxi riders can sip City Winery’s special Chicago-themed wines as the boat cruises the river and pauses near Navy Pier to take in a stunning fireworks display after sunset. Visitors can decide whether an all-day pass, a 10-ride pass, or a one-way ticket is most appropriate for their particular trip. This mode of transport is also the most exciting way to get to Chinatown, which is a must-visit for anyone seeking adventure in the restaurant department.

Snack Planet Corporation

Restaurant, Chinese

© Yinan Chen / WikiCommons

This Chinatown staple serves up traditional Chinese cuisine with a modern twist. Snack Planet Corporation offers tons of options, including stir-fried dishes, noodle entrées, cold appetizers, and plates of unusual ingredients. For instance, Snack Planet serves up Bean Sprout Stir Fry with Intestines, Spicy Pig Offal (internal organs), Intestines with Spicy Pickled Cabbage, and Spicy Frog Legs—definitely an adventurous menu. Try a few items or a bunch; the prices are great, making mixing and matching an easy and tempting option.

The restaurant is also said to work well with LaoGanMa, a black bean chili paste indigenous to northern China and often used in the region’s cuisine. So, hop on the water taxi to Chinatown for another wild ride—this time, with food!

Maggie Daley Park


Maggie Daley Park
© Monicaacosta34 / WikiCommons

Located just outside Millennium Park in downtown Chicago, Maggie Daley Park features tons of activities for people of all ages. The site offers a playground for kids, mini golf, picnic tables, a skating rink, and more. For the adventure seeker, the climbing wall may be of interest.

Managed by Lakeshore Sport & Fitness, the wall has areas for both beginner and expert climbers. Adventurers can choose from bouldering, lead-harness, and top roping, depending on skill level. The wall spans 19,000 square feet (1,765.1 square meters), and at its tallest, it is 40 feet (12.19 meters) high. If you climb or boulder regularly, don’t worry about lugging equipment; everything necessary to climb at Maggie Daley Park is available for rent. While the park is free, climbing the wall is a small extra fee, but totally worth it to get a little adventure into the day.

Art Institute of Chicago


© Pinotgris / WikiCommons
For a slightly different type of adventure seeker, the Art Institute of Chicago might be the optimal destination. Watson Adventures, a company that specializes in scavenger hunts in public spaces, designed several challenges specifically for the Art Institute of Chicago. Through the Watson Adventures site, participants can join in public scavenger hunts with unique goals and games to make visiting one of the world’s best art museums a little more exciting. There are options to form private hunts and challenges too.

Fans of escape room events will find this type of adventure super enjoyable. For instance, one hunt involves uncovering clues throughout the museum that will unlock a “box” containing the “antidote” to a “poison” that will “kill” participants if they don’t reach the solution in time! The puzzle involves riddles, interaction with museum staff, teamwork, quick thinking, and many more skills most risk-takers have already developed over years of pushing themselves to wild limits.
culture trip left arrow
 culture trip brand logo

Volcanic Iceland Epic Trip

meet our Local Insider


women sitting on iceberg


2 years.


It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.


I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!

culture trip logo letter c
group posing for picture on iceberg
group posing for picture on iceberg

Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.

map of volcanic iceland trip destination points
culture trip brand logo
culture trip right arrow
landscape with balloons floating in the air


Connect with like-minded people on our premium trips curated by local insiders and with care for the world

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.