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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 October , November 2026

28 Oct - 11 Nov $ 114.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
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21 Oct - 10 Nov $ 202.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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21 Oct - 02 Nov $ 289.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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Last minute flights from Orlando to Chicago

28 Oct - 31 Oct $ 198.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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27 Oct - 31 Oct $ 257.00
ORL
Orlando
Frontier Airlines
1 STOPS
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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28 Oct - 31 Oct $ 530.00
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

7:00 AM - 7:00 AM
Allegiant Air
0 Stops
2h 44m
ORL - CHI
$ 59
Kiwi
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5:40 AM - 5:40 AM
Frontier Airlines
0 Stops
3h 11m
ORL - CHI
$ 129
Kiwi
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12:27 PM - 12:27 PM
United Airlines
0 Stops
3h 2m
ORL - CHI
$ 236
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.