Cheap flights from Chicago to Lakeland - Winter Haven

View AU$121 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
Tue, 14 Oct. - Tue, 21 Oct.
ORD
Chicago
MCO
Orlando
AU$244 Return, found 4 days ago
AU$244
Return
found 4 days ago
Select American Airlines flight, departing Tue, 14 Oct. from Chicago to Orlando, returning Tue, 21 Oct., priced at AU$244 found 4 days ago
American Airlines
Sat, 23 Aug. - Sun, 24 Aug.
ORD
Chicago
MCO
Orlando
AU$272 Return, found 1 day ago
AU$272
Return
found 1 day ago
Select American Airlines flight, departing Sat, 23 Aug. from Chicago to Orlando, returning Sun, 24 Aug., priced at AU$272 found 1 day ago
American Airlines
Tue, 12 Aug. - Wed, 13 Aug.
ORD
Chicago
MCO
Orlando
AU$275 Return, found 6 days ago
AU$275
Return
found 6 days ago
Select American Airlines flight, departing Tue, 12 Aug. from Chicago to Orlando, returning Wed, 13 Aug., priced at AU$275 found 6 days ago
Delta
Tue, 12 Aug. - Wed, 13 Aug.
ORD
Chicago
MCO
Orlando
AU$305 Return, found 6 days ago
AU$305
Return
found 6 days ago
Select Delta flight, departing Tue, 12 Aug. from Chicago to Orlando, returning Wed, 13 Aug., priced at AU$305 found 6 days ago
United
Tue, 2 Sep. - Tue, 9 Sep.
ORD
Chicago
TPA
Tampa
AU$335 Return, found 5 days ago
AU$335
Return
found 5 days ago
Select United flight, departing Tue, 2 Sep. from Chicago to Tampa, returning Tue, 9 Sep., priced at AU$335 found 5 days ago
Alaska Airlines
Sun, 7 Sep. - Wed, 24 Sep.
ORD
Chicago
MCO
Orlando
AU$1,048 Return, found 4 days ago
AU$1,048
Return
found 4 days ago
Select Alaska Airlines flight, departing Sun, 7 Sep. from Chicago to Orlando, returning Wed, 24 Sep., priced at AU$1,048 found 4 days ago
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