Cheap flights from Chicago to Lower Keys

View AU$279 flight on Tue, 19 Aug. 2025Opens in a new window

Popular airlines from Chicago to Lower Keys

  • Delta

    Delta

  • American Airlines

    American Airlines

  • United

    United

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 35% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in

Cheap Flights from Chicago (CHI) to Lower Keys (EYW)

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.

Delta
Fri, 8 Aug. - Wed, 13 Aug.
MDW
Chicago
EYW
Key West
AU$411 Return, found 2 days ago
AU$411
Return
found 2 days ago
Select Delta flight, departing Fri, 8 Aug. from Chicago to Key West, returning Wed, 13 Aug., priced at AU$411 found 2 days ago
Delta
Tue, 19 Aug. - Tue, 26 Aug.
ORD
Chicago
EYW
Key West
AU$411 Return, found 1 day ago
AU$411
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug. from Chicago to Key West, returning Tue, 26 Aug., priced at AU$411 found 1 day ago
Delta
Wed, 13 Aug. - Wed, 20 Aug.
MDW
Chicago
EYW
Key West
AU$413 Return, found 6 days ago
AU$413
Return
found 6 days ago
Select Delta flight, departing Wed, 13 Aug. from Chicago to Key West, returning Wed, 20 Aug., priced at AU$413 found 6 days ago
Delta
Tue, 19 Aug. - Tue, 26 Aug.
MDW
Chicago
EYW
Key West
AU$441 Return, found 1 day ago
AU$441
Return
found 1 day ago
Select Delta flight, departing Tue, 19 Aug. from Chicago to Key West, returning Tue, 26 Aug., priced at AU$441 found 1 day ago
American Airlines
Tue, 19 Aug. - Tue, 26 Aug.
ORD
Chicago
EYW
Key West
AU$492 Return, found 1 day ago
AU$492
Return
found 1 day ago
Select American Airlines flight, departing Tue, 19 Aug. from Chicago to Key West, returning Tue, 26 Aug., priced at AU$492 found 1 day ago
United
Tue, 19 Aug. - Tue, 26 Aug.
ORD
Chicago
EYW
Key West
AU$781 Return, found 1 day ago
AU$781
Return
found 1 day ago
Select United flight, departing Tue, 19 Aug. from Chicago to Key West, returning Tue, 26 Aug., priced at AU$781 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 AU$287 - AU$963 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.