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

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
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How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)

How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)
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How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)
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How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)
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Cheap flights from Orlando to Chicago in May , June 2026

30 May - 29 Jun $ 115.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
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27 May - 10 Jun $ 144.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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27 May - 09 Jun $ 186.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
Pick dates

Last minute flights from Orlando to Chicago

27 May - 31 May $ 237.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
1 STOPS
ORL
Orlando
Pick dates
27 May - 31 May $ 296.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
Pick dates
27 May - 31 May $ 548.00
ORL
Orlando
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
ORL
Orlando
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One-way flights to Chicago from Orlando

7:30 AM - 7:30 AM
Allegiant Air
0 Stops
2h 51m
ORL - CHI
$ 67
Kiwi
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8:58 PM - 8:58 PM
Frontier Airlines
0 Stops
3h 15m
ORL - CHI
$ 72
Kiwi
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12:45 PM - 12:45 PM
United Airlines
0 Stops
3h 2m
ORL - CHI
$ 109
Kiwi
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How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Orlando (ORL) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.