In Chicago, you get to pick your own adventure, whether it's flying over the city in a helicopter, watching pyrotechnics from your kayak, flying high on a flyboard, or escaping from the confines of a goldmine.

Chicago Helicopter Tours

Soar Above the City & Lake in a Helicopter

Get your thrill-seeking fix while taking in Chicago's dramatic city and lake views from your seat in a Chicago Helicopter Experience chopper. Choose from daytime, twilight or nighttime trips, taking off from the Chinatown area. Or fly with Vertiport Chicago from their world-class heliport located downtown. Choose from day and night tours, or create your own custom experience.

wh kayaking

Kayak Along the Chicago Riverwalk 

Explore the city from a completely different vantage point: The water. Head down to the Chicago Riverwalk and rent a kayak to explore the waterway on your own, or take a guided tour with Urban Kayaks or Wateriders. You'll pass by pedestrian walkways, architectural masterpieces and dramatic city views, all while enjoying the great outdoors. For a little extra excitement, Kayak down the Chicago River at night, through the city and out to Navy Pier to watch the fireworks. Check out Kayak ChicagoWateriders and Urban Kayaks for details. Rental rates start at around $30 per hour, per person.

Climbing wall at Maggie Daley Park in Chicago

Rock Climb at Maggie Daley Park 

Test your skills at Chicago's first and only outdoor climbing park at Chicago's newest downtown green space, Maggie Daley Park. Featuring two rock-climbing structures divided into a beginner and advanced climb, these surfaces can accommodate between 25 and 100 climbers at any given time. Best of all, you get spectacular Chicago skyline views. The climbing wall is open April through October, and works on a first-come-first-served basis.

The Escape Room

Escape from a Mine (or a Spaceship, or a Prison...)

Take the adventure indoors with The Escape Game Chicago in River North, which puts you in one of four time-pressured, high-stakes scenarios: Gold Rush (pictured above), Prison Break, The Heist and Mission: Mars. The various sets are the most elaborate you'll likely ever see, with the goal of giving you the most realistic experience possible. With all the sound effects, puzzles, clues and countdown reminders, things got pretty intense pretty quick. Tickets start at $34.99, and private room bookings at $279.

Seadog Cruises

Ride the River on a Speedboat

Wave your perfect hair goodbye as you launch across the waters of the Chicago River in a high-speed boat. Sea dog Cruises promises you full-throttle slalom runs, sharp twists and turns, and the raw power of two 1400 HP engines. You'll also enjoy music and a fun narration about Chicago throughout your cruise. A word of warning: YOU WILL GET WET! A 30-minute ride will cost you from $31.95 for adults, and $23.95 for children.

Jet ski on Lake Michigan

Looking for an adrenaline rush?  Zoom across the surface of Lake Michigan with a jet ski rental. The fleet at Chicago Water Sport Rentals at 31st Street Beach consists of the new Sea Doo Spark and Yamaha VX Cruiser jet skis. With each rental, you'll be provided with a Coast Guard approved life vest, personal watercraft orientation and wetsuits (upon request). Rates start at $59 for 30 minutes. Licensed by the Chicago Park District, ​Jet Ski Chicago at North Avenue Beach is the only provider of jet skis for the Chicago beach area.  Rates start at $85 for 30 minutes.

Chicago Water Sport Rentals Flyboard

Try Your Hand at Flyboarding

Try something completely out of the ordinary with a flyboard rental from Chicago Water Sports Rentals at 31st Street Harbor. Similar to a snowboard but connected to a jet ski, the flyboard allows riders to soar over the water for the ultimate adrenaline rush. As Chicago Water Sports Rentals describes it, "The arrangement lets you fly, Iron Man style, up to 40 feet in the air – or leap headfirst through the waves like a human dolphin."  Call 312-924-7994 for rates and information, 

Skate Board at Grant Park

It's not only skateboarders who love the Skate Park in Grant Park. You'll see rollerbladers and BMX bike enthusiasts making the most of the park's multi-skill level concrete ramps, grinding rails and handrails, bench seating and native landscape plantings — all with a lakefront view.

Step onto a Ledge, Then Take a Tilt 

Skydeck at Willis Tower

@Skydeck at Willis Tower​

More than 100 stories up the Willis Tower lies Skydeck Chicago, an absolute can't-miss Chicago experience. Open daily, it offers spectacular views crossing four states on a clear day, interactive exhibits and — drumroll, please — The Ledge, a glass box that allows you step four feet outside the walls of the building, as though you're walking on air. Up the thrill ante by taking a trip to 875 N. Michigan (formerly the John Hancock Building) on the Magnificent Mile, where the 94th floor observatory, 360 Chicago, will literally tilt you over the city 1000 ft. up.


Save 50% on premium admission to Chicago’s top attractions with CityPASS tickets.  

Includes prepaid admission to 5 must-see attractions:

Valid for 9 consecutive days, Chicago CityPASS tickets cost $108 for adults (value $214) and $89 for children ages 3-11. Buy online at or at any CityPASS attraction.

Spend less, experience more.


Save up to 45% on admission to over 25 top Chicago attractions with Go Chicago Card. Choose the number of days you wish to use the pass from 1, 2, 3, or 5 calendar days in a row and enjoy exploring Chicago’s best sights. Visit top attractions like the Shedd Aquarium, Shoreline Architecture River Cruise, 360 Chicago and more. Passes must be used within a year of purchase and are activated once you visit your first attraction

Find more Chicago Guides & Bucket Lists here.


Featured Partners