Beginning of main content

7,800 Travelers rated Chicago highly for Urban and Skyscrapers

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Top Car Deals in Chicago

See all Chicago car rentals

Car Rentals in Chicago

Chicago, Illinois is home to one of the most famous skylines in the world, along with a packed lineup of the arts, culture, high fashion, architecture, and cuisine. It’s one of those “can’t miss it” destinations in the United States, where Midwest comfort comes to life with a metropolitan flair.

As the third largest city in the United States, exploring Chicago to the fullest is best done in the driver’s seat with a trusty GPS by your side. Make the eclectic and lively downtown metro your homebase, and explore the city in all directions at leisure with your own set of wheels.


What to See in Chicago

Admire the famous downtown Chicago skyline to start your trip off on the right foot. With many visitors flocking to Willis Tower, also known as the Sears Tower, skip the crowds by going to the John Hancock building instead. Up here, grab a cocktail at the Signature Room on the 95th floor and gaze out at Chicago’s impressive architectural jungle in comfort.

Alternatively, head out into the city for a dose of science, history, and art. Chicago is home to world-class museums, and fitting a few into your itinerary is definitely worth it. Admire impressionist works at the Art Institute of Chicago, get your hands on at the Museum of Science and Industry, and take a walk back in time at the Field Museum, which is home to the most complete Tyrannosaurus Rex fossil.

Then, grab your wallet and shop until you drop. Michigan Avenue – the “Magnificent Mile” – is known for high-end fashion and trendy stores, but that’s not all Chicago has to offer to the avid buyer. Head to the Wicker Park neighborhood for boutique designs, browse the vintage racks in the Boystown neighborhood, or stop by the River North district for art gallery and home good pieces. A trip to the “World’s Largest Jazz and Blues Record Store”, known as Jazz Record Mart, might score you the elusive vinyl you’ve been searching for.

When hunger strikes, make sure to grab a slice of Chicago’s famous deep-dish pizza, but save room for dessert at Rainbow Cone – a favorite local ice cream and yogurt shop.

Don’t leave Chicago without viewing a legendary city show. The Lyric Opera is a cultural institution known for lavish performances. Second City is home to hilarious improv and a night of laughter. The Chicago Shakespeare Theatre not only displays incredible talent, but the theater itself offers stunning views of the city from Navy Pier.

Finally, catch a game at Wrigley Field. This iconic baseball stadium is home to the Chicago Cubs and the retro vibe of the field will make your heart sing for the red, white, and blue. Tickets rarely sell out, so buy at discounted rates on the day of the game.


Car Rental with Orbitz

No matter your itinerary, the options for exploring Chicago are endless with access to your own car. Skip the cab fare and wait-time that accompany city taxis and takeoff at your own pace with our budget friendly and hassle-free rental options at Orbitz.