Cheapest flights from Chicago

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Aug 19 - Tue, Sep 9

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 1 day ago

$269

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 19 from O'Hare Intl. to Key West Intl., returning Tue, Sep 9, priced at $269 found 1 day ago

Tue, Jul 22 - Tue, Aug 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$289 Roundtrip, found 1 day ago

$289

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 22 from O'Hare Intl. to Key West Intl., returning Tue, Aug 12, priced at $289 found 1 day ago

Wed, Jul 9 - Fri, Jul 25

ORD

O'Hare Intl.

EYW

Key West Intl.

$309 Roundtrip, found 1 day ago

$309

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Jul 9 from O'Hare Intl. to Key West Intl., returning Fri, Jul 25, priced at $309 found 1 day ago

Tue, Aug 5 - Tue, Aug 26

ORD

O'Hare Intl.

EYW

Key West Intl.

$311 Roundtrip, found 1 day ago

$311

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Key West Intl., returning Tue, Aug 26, priced at $311 found 1 day ago

Sat, Jul 26 - Tue, Aug 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$320 Roundtrip, found 1 day ago

$320

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Key West Intl., returning Tue, Aug 12, priced at $320 found 1 day ago

Sun, Jul 27 - Tue, Aug 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$324 Roundtrip, found 1 day ago

$324

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Jul 27 from O'Hare Intl. to Key West Intl., returning Tue, Aug 12, priced at $324 found 1 day ago

Wed, Nov 5 - Wed, Nov 19

ORD

O'Hare Intl.

EYW

Key West Intl.

$327 Roundtrip, found 1 day ago

$327

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Nov 5 from O'Hare Intl. to Key West Intl., returning Wed, Nov 19, priced at $327 found 1 day ago

Tue, Jul 22 - Wed, Aug 13

ORD

O'Hare Intl.

EYW

Key West Intl.

$331 Roundtrip, found 1 day ago

$331

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 22 from O'Hare Intl. to Key West Intl., returning Wed, Aug 13, priced at $331 found 1 day ago

Mon, Jan 12 - Mon, Feb 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$339 Roundtrip, found 1 day ago

$339

Roundtrip

found 1 day ago

Select United flight, departing Mon, Jan 12 from O'Hare Intl. to Key West Intl., returning Mon, Feb 2, priced at $339 found 1 day ago

Tue, Jul 22 - Mon, Aug 11

ORD

O'Hare Intl.

EYW

Key West Intl.

$344 Roundtrip, found 1 day ago

$344

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Jul 22 from O'Hare Intl. to Key West Intl., returning Mon, Aug 11, priced at $344 found 1 day ago

Wed, Oct 22 - Wed, Nov 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$347 Roundtrip, found 1 day ago

$347

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 22 from O'Hare Intl. to Key West Intl., returning Wed, Nov 12, priced at $347 found 1 day ago

Sat, Nov 15 - Tue, Dec 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$348 Roundtrip, found 1 day ago

$348

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Nov 15 from O'Hare Intl. to Key West Intl., returning Tue, Dec 2, priced at $348 found 1 day ago

Tue, Aug 19 - Tue, Sep 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$349 Roundtrip, found 1 day ago

$349

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 19 from O'Hare Intl. to Key West Intl., returning Tue, Sep 2, priced at $349 found 1 day ago

Fri, Oct 24 - Wed, Nov 5

ORD

O'Hare Intl.

EYW

Key West Intl.

$351 Roundtrip, found 1 day ago

$351

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Fri, Oct 24 from O'Hare Intl. to Key West Intl., returning Wed, Nov 5, priced at $351 found 1 day ago

Tue, Aug 5 - Wed, Aug 20

ORD

O'Hare Intl.

EYW

Key West Intl.

$354 Roundtrip, found 1 day ago

$354

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 5 from O'Hare Intl. to Key West Intl., returning Wed, Aug 20, priced at $354 found 1 day ago

Thu, Jan 8 - Thu, Jan 22

ORD

O'Hare Intl.

EYW

Key West Intl.

$359 Roundtrip, found 1 day ago

$359

Roundtrip

found 1 day ago

Select United flight, departing Thu, Jan 8 from O'Hare Intl. to Key West Intl., returning Thu, Jan 22, priced at $359 found 1 day ago

Sat, Jul 26 - Wed, Aug 13

ORD

O'Hare Intl.

EYW

Key West Intl.

$362 Roundtrip, found 1 day ago

$362

Roundtrip

found 1 day ago

Select Delta flight, departing Sat, Jul 26 from O'Hare Intl. to Key West Intl., returning Wed, Aug 13, priced at $362 found 1 day ago

Sun, Jul 27 - Wed, Aug 13

ORD

O'Hare Intl.

EYW

Key West Intl.

$366 Roundtrip, found 1 day ago

$366

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Jul 27 from O'Hare Intl. to Key West Intl., returning Wed, Aug 13, priced at $366 found 1 day ago

Wed, Jul 2 - Tue, Jul 15

ORD

O'Hare Intl.

EYW

Key West Intl.

$369 Roundtrip, found 1 day ago

$369

Roundtrip

found 1 day ago

Select United flight, departing Wed, Jul 2 from O'Hare Intl. to Key West Intl., returning Tue, Jul 15, priced at $369 found 1 day ago

Sat, Nov 8 - Tue, Nov 25

ORD

O'Hare Intl.

EYW

Key West Intl.

$383 Roundtrip, found 1 day ago

$383

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Nov 8 from O'Hare Intl. to Key West Intl., returning Tue, Nov 25, priced at $383 found 1 day ago