$44 Cheap Rental Cars Chicago, IL

From a scenic drive along Lake Shore Drive to a cruise down the Magnificent Mile, Chicago was made to be explored by car. Sure, you could walk along the lake or take a cab through downtown, but it’s so much more enjoyable to rent a car in Chicago and hit The Loop when you’re the one behind the wheel. The third-largest city in the United States, Chicago is a colorful and dynamic place to visit, whether you’re in town on a business trip or for your annual family vacation.

Located on the southwest corner of Lake Michigan, this booming metropolis offers cultural, comedic, and culinary experiences like no other town in the country. And thanks to its rich historical background and its thriving arts scene, there’s tons to do between stops at blues clubs, improv performances, and pizza parlors. There is one other thing to note: Make sure pack a windbreaker and tie back your hair. It’s called the Windy City for a reason, after all. And, when you use Travelocity to reserve a convertible rental car in Chicago (preferably in the summertime), you can use the wind to your advantage.

Where Are the Best Places to Stay in Chicago?

Chicago boasts a wealth of attractions throughout the greater metropolitan area—from Indiana Dunes National Lakeshore in the south to Illinois State Beach Park up north. The best place to stay so you can be central to all is right downtown. Here are some of our favorite hotels in Chicago:

• Congress Plaza Hotel – A true landmark hotel in every sense of the word, The Congress Plaza has been Chicago’s standard of luxury and hospitality since 1893. Grab breakfast at the casual Gazebo, enjoy a fine meal at the end of your day at Rafael’s, and sip on a craft cocktail at the Congress Lounge before retiring to your comfortable guest room.
• Hyatt Regency – Contemporary sophistication rules the day at the Hyatt Regency. The AAA Four Diamond property is right on Upper Wacker Drive—as well as next to the Chicago Riverwalk—making a scenic drive or stroll very convenient. And valet parking makes it easy on the return trip, too. Although with three amazing bars and eateries, 240,000 square feet of meeting space, and 2,000+ well-appointed guest rooms, you may never want to leave.
• Wyndham Grand Chicago Riverfront – The best views of Chicago’s skyline are from a vantage point within it. Nestled along a bend in the Chicago River, the Wyndham Grand offers sweeping vistas of the concrete and metal monoliths that helped make the city famous. Enjoy valet parking, an in-room massage, and happy hour at Hoyt’s in between your time spent at the city’s attractions.
• The Palmer House Hilton – If you are hosting a destination event, look no further than the Palmer House. With seven exquisite ballrooms, a lobby to make Hollywood drool, and luxurious accommodation, it’ll be an unforgettable evening. Additionally, the property is just a two-block stroll to the Art Institute of Chicago, and another two blocks to Lake Sure Drive for your scenic road trip along Lake Michigan.

Driving in and Around Chicago

The easiest place to find rental cars in Chicago is at the city’s airports. Both O'Hare International Airport and Chicago Midway International Airport offer convenient rentals. You can grab your keys while you are waiting for your luggage to hit the baggage claim carousel, and you’ll be on your way to your hotel in no time. Downtown Chicago hotels are about a 15-mile drive from either airport.

A rental car is a must if you want to visit some of the open areas surrounding the city, such as the forest preserves to the north and northwest. They're great places for an impromptu picnic or a leisurely bike ride, and have more than enough shady forest trails for a hike or a jog. The Brookfield Zoo, with its exotic bird displays, is another popular attraction that is worth the drive from anywhere in Chicagoland. When you've had your fill of skyscraper-filled skylines, head out to Glencoe for the blooming flowers and plant habitats at the Chicago Botanic Garden.

Explore Chicago

Let Travelocity help you find great Chicago rental car deals. Additionally, when you use the Travelocity app, you can access mobile-exclusive offers on travel to Chicago. Book your hotel and flights to Chicago at the same time, and you can save even more money. Travelocity makes it easy to book hotels and rental cars near Chicago’s hottest attractions at any time of year. Our intuitive reservation system is the best on the web, and presents you with deals on cheap car rentals in Chicago you won’t find anywhere else.

Lock down your Chicago rental car today and you’ll be exploring the Windy City before you know it. And with the money you save, you can settle one mankind’s most timeless debates: Which is better—a Chicago hot dog or deep-dish pizza?

Here at Travelocity, we’re committed to helping you score cheap deals on Chicago car rentals. We’ll have your rental car waiting for you as soon as you arrive in town. Traveling with your whole family in tow? Choose a spacious and affordable van to keep your crew sane throughout the trip. Exploring the city with your sweetheart? Reserve a swanky two-seater as you paint the town red. With our low rates on rental cars in Chicago, you can go out and smell the roses, without stressing out your bank account. You can even use our mobile booking app to snag exclusive deals, so you can spend more on your adventures and less on your vehicle.