Cheap flights from Chicago to Lakeland - Winter Haven

View AU$119 flight on Tue, 16 Sep. 2025Opens in a new window

Popular airlines from Chicago to Lakeland - Winter Haven

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Chicago (CHI) to Lakeland - Winter Haven (ORL)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 20 Sep. - Sat, 27 Sep.
ORD
Chicago
MCO
Orlando
AU$238 Return, found 4 hours ago
AU$238
Return
found 4 hours ago
Select American Airlines flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$238 found 4 hours ago
American Airlines
Sun, 14 Sep. - Fri, 19 Sep.
ORD
Chicago
MCO
Orlando
AU$242 Return, found 22 hours ago
AU$242
Return
found 22 hours ago
Select American Airlines flight, departing Sun, 14 Sep. from Chicago to Orlando, returning Fri, 19 Sep., priced at AU$242 found 22 hours ago
American Airlines
Thu, 11 Sep. - Thu, 18 Sep.
ORD
Chicago
MCO
Orlando
AU$271 Return, found 22 hours ago
AU$271
Return
found 22 hours ago
Select American Airlines flight, departing Thu, 11 Sep. from Chicago to Orlando, returning Thu, 18 Sep., priced at AU$271 found 22 hours ago
Delta
Sat, 20 Sep. - Sat, 27 Sep.
MDW
Chicago
MCO
Orlando
AU$299 Return, found 4 hours ago
AU$299
Return
found 4 hours ago
Select Delta flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$299 found 4 hours ago
United
Sat, 20 Sep. - Sat, 27 Sep.
ORD
Chicago
MCO
Orlando
AU$345 Return, found 4 hours ago
AU$345
Return
found 4 hours ago
Select United flight, departing Sat, 20 Sep. from Chicago to Orlando, returning Sat, 27 Sep., priced at AU$345 found 4 hours ago
Alaska Airlines
Sun, 7 Sep. - Wed, 24 Sep.
ORD
Chicago
MCO
Orlando
AU$1,048 Return, found 6 days ago
AU$1,048
Return
found 6 days ago
Select Alaska Airlines flight, departing Sun, 7 Sep. from Chicago to Orlando, returning Wed, 24 Sep., priced at AU$1,048 found 6 days ago
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