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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 August , September 2026

31 Aug - 26 Sep $ 184.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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25 Aug - 09 Sep $ 185.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
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25 Aug - 06 Sep $ 224.00
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
Pick dates

Last minute flights from Orlando to Chicago

29 Aug - 31 Aug $ 165.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
Pick dates
25 Aug - 31 Aug $ 168.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
Pick dates
26 Aug - 31 Aug $ 168.00
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
Pick dates

One-way flights to Chicago from Orlando

4:26 PM - 4:26 PM
Allegiant Air
0 Stops
2h 48m
ORL - CHI
$ 102
Kiwi
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9:00 PM - 9:00 PM
Frontier Airlines
0 Stops
3h 8m
ORL - CHI
$ 109
Kiwi
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9:55 AM - 9:55 AM
United Airlines
0 Stops
3h 4m
ORL - CHI
$ 178
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.