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Flight Deals from Orlando to Chicago from $39
Top flight deals from leading airlines:
... and +100s more
Cancel within 24 hours for a full refund—no questions asked.
We’ll refund the difference if the price drops before you fly.
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Stops
- Nonstopfrom $248
- Up to 1 stop$303
- Up to 2 stops$337
Airlines
- American Airlines$298
- United Airlines$248
Cabin Class
- Economy$248
Departure Airports
- Orlando International Airport$248
Arrival Airports
- Chicago O Hare Airport$248
Layover Airports
- Charlotte Douglas International Airport$303
- Detroit Metropolitan Airport$337
- New York LaGuardia Airport$337
- Newark Liberty Airport$364
- Washington Dulles Airport$342
Top Deals on flights from Orlando to Chicago
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 5
as low as
$39
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 5
as low as
$40
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 5
as low as
$65
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 6
as low as
$66
Orlando, US (ORL) - Chicago, US (CHI)
Dec 13
Dec 13
as low as
$75
Orlando, US (ORL) - Chicago, US (CHI)
Dec 12
Dec 12
as low as
$75
Orlando, US (ORL) - Chicago, US (CHI)
Nov 7
Nov 7
as low as
$75
Orlando, US (ORL) - Chicago, US (CHI)
Nov 15
Nov 15
as low as
$76
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 5
as low as
$79
Orlando, US (ORL) - Chicago, US (CHI)
Nov 18
Nov 18
as low as
$98
Orlando, US (ORL) - Chicago, US (CHI)
Dec 5
Dec 5
as low as
$98
Orlando, US (ORL) - Chicago, US (CHI)
Feb 19
Feb 19
as low as
$108
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