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Lowest round trip fares by airline from Orlando and Chicago

Cheapest prices ($19 One Way, $37 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Great Deals On Cheap Hotels in Chicago

Freehand Chicago
3.5 out of 5.0
4.4 out of 5 (14 reviews)

Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

I didn’t like that there wasn’t a little fridge in every room or there wasn’t a coffee pot or a glass for water.
Travelodge by Wyndham Downtown Chicago
2.0 out of 5.0
3.0 out of 5 (39 reviews)

Located in The Loop, this hotel is steps from Columbia College Chicago, Grant Park, and State Street. Art Institute of Chicago and Buckingham Fountain are also ...

It was an excellent location close to everything. Staff kind and very helpful. Great experience
Motel 6 Elk Grove Village, IL - O'Hare
2.0 out of 5.0
3.5 out of 5 (14 reviews)

Situated in Elk Grove Village, this hotel is 2.1 mi (3.3 km) from Lake Park and 2.8 mi (4.6 km) from Allstate Arena. Apache Park is 2.9 mi (4.7 km) away.

Room was very clean and neat and when asked to change the sheets they do so fast. Very friendly staff very helpfully would forsure go back again when im in town

Fly From Orlando to Chicago

Number of Daily Flights25
Earliest Flight Departure DateJul 11
Latest Flight Departure DateJul 12
Popular AirlinesAmerican Airlines

Cheap flights from Orlando to Chicago

Cheap flights from Orlando to Chicago

First-time visitors headed to Chicago from Orlando may be in for a bit of culture shock. The Windy City boasts an impressive skyline that you'll see long before you land at O'Hare International Airport (ORD). Some of the world's tallest buildings call Chicago home, including the former record holder, Willis Tower. Locals still refer to the famous skyscraper as the Sears Tower, and brave visitors can take an elevator ride to the observation deck 103 floors up from the lobby.

Key Facts

Greater Chicagoland is served by the Chicago Transit Authority, which operates buses, trains and subway lines throughout the city. Since Chicago is such a sprawling metropolis, the best way to see as many sights as possible, is to opt for a rental car. In general, navigation in Chicago is easy as the streets are set up in a grid, but you may want to opt for an in-vehicle GPS, as the city spans more than 235 square miles.

Hints and Tips

If you're on a direct flight from Orlando International Airport (MCO) to Chicago, you'll be in the air for less than three hours. O'Hare is a family-friendly facility that houses a replica airport playground in Terminal 2, where children can pretend to be pilots and unwind after a flight. For your convenience, a variety of rental car companies offer free shuttle service outside of baggage claim.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.