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

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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 Chicago (CHI) to Orlando (ORL)

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

28 May - 03 Jun $ 109.00
CHI
Chicago
Allegiant Air
DIRECT
ORL
Orlando
ORL
Orlando
Allegiant Air
DIRECT
CHI
Chicago
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12 May - 09 Jun $ 232.00
CHI
Chicago
Frontier Airlines
1 STOPS
ORL
Orlando
ORL
Orlando
Frontier Airlines
1 STOPS
CHI
Chicago
Pick dates
03 May - 16 Jun $ 588.00
CHI
Chicago
United Airlines
DIRECT
ORL
Orlando
ORL
Orlando
United Airlines
DIRECT
CHI
Chicago
Pick dates

Last minute flights from Chicago to Orlando

28 May - 31 May $ 228.00
CHI
Chicago
Frontier Airlines
DIRECT
ORL
Orlando
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
Pick dates
12 May - 31 May $ 320.00
CHI
Chicago
Frontier Airlines
1 STOPS
ORL
Orlando
ORL
Orlando
Frontier Airlines
DIRECT
CHI
Chicago
Pick dates
09 May - 31 May $ 454.00
CHI
Chicago
United Airlines
DIRECT
ORL
Orlando
ORL
Orlando
United Airlines
DIRECT
CHI
Chicago
Pick dates

One-way flights to Orlando from Chicago

5:11 PM - 5:11 PM
Frontier Airlines
0 Stops
3h 2m
CHI - ORL
$ 34
Kiwi
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1:59 PM - 8:07 PM
Frontier Airlines
1 Stops
6h 48m
CHI - ORL
$ 126
Kiwi
Pick dates
10:52 AM - 10:52 AM
United Airlines
0 Stops
2h 55m
CHI - ORL
$ 224
Kiwi
Pick dates

How to find the cheapest flight from Chicago (CHI) to Orlando (ORL)

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