Important: This destination may have COVID-19 travel restrictions in place, including specific restrictions for lodging. Check any national, local, and health advisories for this destination before you book.

Cheap flights from Orlando (ORL) to Chicago (CHI)

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Lowest round trip fares by airline from Orlando and Chicago

Cheapest prices ($43 One Way, $80 Round Trip) found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, May 26
MCO
Orlando
ORD
Chicago
$43
United
Tue, May 25
MCO
Orlando
ORD
Chicago
$53
Frontier Airlines
Wed, Jun 9
MCO
Orlando
ORD
Chicago
$57
Spirit Airlines
Wed, Jun 16
MCO
Orlando
ORD
Chicago
$63
Frontier Airlines
Thu, May 27
MCO
Orlando
ORD
Chicago
$65
Frontier Airlines
Tue, May 25 - Tue, May 25
MCO
Orlando
ORD
Chicago
$80
United
Tue, May 25 - Tue, May 25
MCO
Orlando
ORD
Chicago
$85
United
Wed, May 19 - Thu, May 20
MCO
Orlando
ORD
Chicago
$87
Spirit Airlines
Thu, May 20 - Tue, May 25
MCO
Orlando
ORD
Chicago
$91
American Airlines
Thu, May 20 - Tue, May 25
MCO
Orlando
ORD
Chicago
$97
American Airlines

Great Deals On Cheap Hotels in Chicago

Freehand Chicago

Freehand Chicago

3.5 out of 5
19 East Ohio Street, Chicago, IL
The price is $94 per night from May 16 to May 16
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 ...
4.3/5Excellent! (15 reviews)
"I like the bunk beds- so interesting. I love the location. It is close to everything. You are in the heart of the city with lots of activities to do! The staff from day one have been so rude, so cold in attitude just unpleasant but I have tried to beasrespectful and polite as I can possibly be - ..."

Reviewed on Sep 21, 2020

Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St, Chicago, IL
The price is $79 per night from May 16 to May 16
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 ...
3.1/5 (9 reviews)
"I liked the close proximity to downtown, Chicago. The two restaurants on the property as well as close parking in which you would need to pay."

Reviewed on Sep 25, 2020

Travelodge by Wyndham Downtown Chicago
Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Elk Grove Village, IL - O'Hare

2 out of 5
2881 Touhy Ave, Elk Grove Village, IL
The price is $40 per night from May 18 to May 18
Situated in Elk Grove Village, this motel 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.
3.8/5Good! (13 reviews)
"Really nice and clean place. The parking lot was clear."

Reviewed on Feb 23, 2021

Motel 6 Elk Grove Village, IL - O'Hare
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fly From Orlando to Chicago

Origin Orlando
Destination Chicago
Number of Daily Flights 47
Earliest Flight Departure Date May 21
Latest Flight Departure Date May 22
Popular Airlines Spirit Airlines

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.