Cheap flights from Chicago to Lower Keys from CA $231

View CA $231 flight on Mon, Nov. 3, 2025Opens in a new window

Popular airlines from Chicago to Lower Keys

  • Air Canada

    Air Canada

  • WestJet

    WestJet

  • Flair Airlines

    Flair Airlines

  • American Airlines

    American Airlines

  • United

    United

  • Delta

    Delta

  • Porter Airlines

    Porter Airlines

  • 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 30% 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 and start at CA $231 for one-way flights and CA $638 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Thu, May 21 - Sun, May 24
ORD
Chicago
EYW
Key West
CA $638 Roundtrip, found 6 days ago
CA $638
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, May 21 from Chicago to Key West, returning Sun, May 24, priced at CA $638 found 6 days ago
American Airlines
Thu, May 21 - Sun, May 24
ORD
Chicago
EYW
Key West
CA $673 Roundtrip, found 6 days ago
CA $673
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, May 21 from Chicago to Key West, returning Sun, May 24, priced at CA $673 found 6 days ago
American Airlines
Thu, May 21 - Sun, May 24
ORD
Chicago
EYW
Key West
CA $702 Roundtrip, found 6 days ago
CA $702
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, May 21 from Chicago to Key West, returning Sun, May 24, priced at CA $702 found 6 days ago
American Airlines
Thu, May 21 - Sun, May 24
ORD
Chicago
EYW
Key West
CA $741 Roundtrip, found 6 days ago
CA $741
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, May 21 from Chicago to Key West, returning Sun, May 24, priced at CA $741 found 6 days ago
American Airlines
Mon, Nov. 3 - Sat, Nov. 29
ORD
Chicago
EYW
Key West
CA $1,054 Roundtrip, found 3 days ago
CA $1,054
Roundtrip
found 3 days ago
Select American Airlines flight, departing Mon, Nov. 3 from Chicago to Key West, returning Sat, Nov. 29, priced at CA $1,054 found 3 days ago
Delta
Mon, Nov. 3 - Sat, Nov. 29
ORD
Chicago
EYW
Key West
CA $1,080 Roundtrip, found 3 days ago
CA $1,080
Roundtrip
found 3 days ago
Select Delta flight, departing Mon, Nov. 3 from Chicago to Key West, returning Sat, Nov. 29, priced at CA $1,080 found 3 days ago

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

November is typically the cheapest month to fly

From CA $258 - CA $865 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.