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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 July , August 2026

28 Jul - 24 Aug $ 185.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
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28 Jul - 04 Aug $ 288.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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28 Jul - 03 Aug $ 313.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
Pick dates

Last minute flights from Orlando to Chicago

28 Jul - 31 Jul $ 230.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
Pick dates
24 Jul - 31 Jul $ 254.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
Pick dates
25 Jul - 31 Jul $ 522.00
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

8:59 PM - 8:59 PM
Frontier Airlines
0 Stops
3h 11m
ORL - CHI
$ 137
Kiwi
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8:59 PM - 8:59 PM
Frontier Airlines
0 Stops
3h 11m
ORL - CHI
$ 161
Kiwi
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12:34 PM - 12:34 PM
United Airlines
0 Stops
3h 8m
ORL - CHI
$ 212
Kiwi
Pick dates

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.