Flights to Florida Keys from Chicago - ￥9,980

View ￥9,980 flight on Sat, Sep 13, 2025Opens in a new window

Popular airlines from Chicago to Florida Keys

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    All Nippon Airways

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    Japan Airlines

  • Jetstar Japan

    Jetstar Japan

  • Solaseed Air

    Solaseed Air

  • STARFLYER

    STARFLYER

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Cheap Flights from Chicago to Florida Keys (CHI-MIA)

Prices were available within the past 7 days and start at ￥9,980 for one-way flights and ￥19,960 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Wed, Sep 24 - Tue, Sep 30
ORD
Chicago
MIA
Miami
￥19,960 Roundtrip, found 4 days ago
￥19,960
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 24 from Chicago to Miami, returning Tue, Sep 30, priced at ￥19,960 found 4 days ago
American Airlines
Wed, Aug 6 - Wed, Aug 13
ORD
Chicago
MIA
Miami
￥22,330 Roundtrip, found 4 days ago
￥22,330
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Aug 6 from Chicago to Miami, returning Wed, Aug 13, priced at ￥22,330 found 4 days ago
American Airlines
Wed, Sep 24 - Tue, Sep 30
ORD
Chicago
MIA
Miami
￥25,770 Roundtrip, found 4 days ago
￥25,770
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 24 from Chicago to Miami, returning Tue, Sep 30, priced at ￥25,770 found 4 days ago
Delta
Wed, Sep 24 - Tue, Sep 30
ORD
Chicago
MIA
Miami
￥25,790 Roundtrip, found 4 days ago
￥25,790
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Sep 24 from Chicago to Miami, returning Tue, Sep 30, priced at ￥25,790 found 4 days ago
American Airlines
Wed, Sep 24 - Tue, Sep 30
ORD
Chicago
MIA
Miami
￥25,880 Roundtrip, found 4 days ago
￥25,880
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Sep 24 from Chicago to Miami, returning Tue, Sep 30, priced at ￥25,880 found 4 days ago
United
Wed, Jul 16 - Fri, Jul 18
ORD
Chicago
MIA
Miami
￥42,860 Roundtrip, found 1 day ago
￥42,860
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jul 16 from Chicago to Miami, returning Fri, Jul 18, priced at ￥42,860 found 1 day ago

Find the cheapest month to fly from Chicago (CHI) to Key West (EYW)

November is typically the cheapest month to fly

From ￥27,388 - ￥91,867 per traveler.

Graph displaying average flight prices per month

*Available to Expedia members.