Top Chicago Transportation Rentals

Arrange for a stress-free ride to O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service. Meet your professional chauffeur at your hotel in downtown Chicago (or other Chicagoland destinations), and relax on the journey to the airport in a private sedan or minivan. You can leave the navigation to someone else, and reach the airport relaxed and in time for your flight.

Ensure a hassle-free arrival at Chicago O'Hare International Airport (ORD) or Midway Airport (MDW) with this private transfer service to your downtown Chicago hotel (or farther-flung Chicagoland destination). Take the stress out of finding a taxi at Chicago's busy airports and book a private vehicle in advance. Travel in style by luxury sedan or SUV that can accommodate up to six passengers.

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

Admire some of the Windy City's most iconic views—and enjoy a time-saving, relaxing way to sightsee—aboard this pet-friendly Chicago River architecture boat tour. With commentary from your onboard guide, watch the spectacular skyline glide by, including dozens of notable buildings, like the Wrigley Building and the John Hancock Building. In just one tour, you cover multiple branches of the Chicago River and learn insider facts and stories you'd otherwise miss.

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.

Explore a new side of Chicago and the city's gangster past on this mafia tour in a coach vehicle. Drive around the Windy City to see where Al Capone, The Untouchables, Hymie Weiss, John Dillinger, and more famous figures hung out. There are ample chances to get out of the bus and pose for pictures in front of a historic courthouse, among other infamous sites.

Enjoy the opportunity to go behind-the-scenes at one of the Windy City's most storied venues on this insider tour of the Chicago Theater. Let your guide lead the way, as you hear about the theater's architecture, history, and famous performers throughout the years. Stand on the famed stage and take in the atmosphere, and see artist signatures from notable performers, including Frank Sinatra and Dolly Parton. A great activity for fans of music and live performance.

Worried about navigating public transportation, or finding your own way to your hotel upon arriving in Chicago? Leave all the logistics to your driver instead—and enjoy a stress-free experience—when you book a private transfer service from either O’Hare or Midway International Airports. Meet your driver after grabbing your bags, hop aboard your air-conditioned vehicle, and relax as you’re whisked straight to your destination.

Discover Chicago in a fun new way—and combine your sightseeing with a lively scavenger hunt—on this two-in-one excursion. With your smartphone in hand, set off at a time that works best for you on this self-led tour. Prompted by the game, explore the Windy City's vibrant Loop neighborhood. You'll spot historic buildings, famous streets, and other local landmarks along the way, all while your party solves clues and challenges.