Top Chicago Rentals

Escape the bustle of the city during this one or two-hour kayak rental along Lake Michigan in downtown Chicago. Experience the serene waters of the iconic lake as you paddle at your own pace in a single or tandem kayak, enjoying views of Chicago’s famous skyline. Take breaks along nearby urban beachfronts, with the option to extend your rental time. Stand-up paddleboards are also available for rental.

Enjoy a performance of the legendary Blue Man Group, one of Chicago’s longest-running shows, at the Briar Street Theater. This worldwide performance troupe, whose hilarious and quirky show has earned them raves in cities around the world, has recently updated their performance with new technology. Experience the group’s gigantic tablet, the “GiPad,” as you enjoy the laugh-inducing antics, stunning visuals and high-tech stage show of this ever-changing, family friendly show. Your ticket purchase also includes a choice of seating options and show times.

See Chicago your way—and enjoy an active way to explore—with this private, half-day bike rental. Make your own way to the rental facility, choose from a range of bike types (from e-bikes and child bikes to premium road bikes), and set off at your own pace. Accompanied by a map and helmet, you can cycle along the water, explore Millennium Park and the Museum Campus, tour Chicago neighborhoods, and more.

Discover Chicago's many delights from the comfort of two wheels. Simply pick up your full-day bike rental with lock, map and helmet and start exploring, either solo or with friends. Make your way through Millennium Park and to historic Wrigley Field, stop for a visit at Navy Pier or spend a couple hours watching sea turtles, penguins and even a piranha at Shedd Aquarium. You get to tour Chicago independently at your own pace and leisure without having to deal with parking or public transit.

Skip the hassle of long taxi lines or crowded airport shuttles and treat yourself to a VIP arrival in Chicago. During this one-way, private car service, you’ll travel comfortably in climate-controlled, newer model sedan with driver to your downtown hotel accommodation. One-way rides include curbside pickup outside the arrivals hall.

Stroll through Chicago's winter streets, lit up for the holidays, on this gourmet walking tour. Learn about Chicago's celebrated holiday traditions like the European-inspired Christkindlmarket, the beautiful decor and windows on State Street, and ice skating at Millennium Park. Sample generous tastes of classic Chicago foods and holiday treats as you walk. Seasonal craft beer tastings help you stay warm and toasty; please note this tour operates in all weather conditions, so dress appropriately.

Discover Chicago in a fun new way on this 3-hour scavenger hunt. Jump into the middle of an exciting adventure around the Chicago Loop — to the historic buildings, famous streets and plethora of real-life locations around town. Discover both well-known and overlooked sites, solving clues and completing challenges via smartphone while learning the local history of the Windy City. Teams of 2- to 5-people are welcome.

It's an intimate experience for 2 to 6 people. No mass crowds associated with tour boats. They get to enjoy the river with the luxury of having their own private boat with a professional, licensed, captain. Cocktails, and other beverages, are available from the bar for purchase before boarding.

The Chicago Outdoor Adventure Pass offers an exhilarating exploration of the city's outdoor attractions. You get 1/2 day (4 hours) bike rental, 2hr kayak rental & 2hr swim. Biking: Enjoy a 20-mile car-free Lakefront Trail ride from Evanston to South Shore Culture Center. Access iconic landmarks like Millennium Park, Grant Park, Buckingham Fountain, and more. Kayaking/SUP: Kayak or paddleboard on Lake Michigan. Ohio Street Beach, with its skyline views, is a prime spot for Instagram-worthy photos. The break wall ensures calm, clear waters, perfect for kayaking and SUP. Don't forget your camera to capture the breathtaking Chicago skyline. Swimming: Get free VIP locker service at Ohio Street Beach, a top-rated Chicago beach. Enjoy a relaxing swim in Lake Michigan without any hassle. Use each part of the pass at your own pace, whether in one day or over 3 days. Immerse yourself in Chicago's natural beauty, recreation, and waterfront views. It's a fantastic way to experience the city!