Flights from Chicago to Key West

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 26 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$269 Roundtrip, found 5 hours ago

$269

Roundtrip

found 5 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $269 found 5 hours ago

Thu, Aug 21 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$289 Roundtrip, found 5 hours ago

$289

Roundtrip

found 5 hours ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $289 found 5 hours ago

Tue, Oct 14 - Sat, Oct 18

ORD

O'Hare Intl.

EYW

Key West Intl.

$309 Roundtrip, found 1 day ago

$309

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to Key West Intl., returning Sat, Oct 18, priced at $309 found 1 day ago

Fri, Aug 22 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$311 Roundtrip, found 5 hours ago

$311

Roundtrip

found 5 hours ago

Select Delta flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $311 found 5 hours ago

Sat, Aug 23 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$324 Roundtrip, found 5 hours ago

$324

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Aug 23 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $324 found 5 hours ago

Tue, Aug 26 - Tue, Sep 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$324 Roundtrip, found 5 hours ago

$324

Roundtrip

found 5 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Tue, Sep 2, priced at $324 found 5 hours ago

Tue, Aug 26 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$331 Roundtrip, found 5 hours ago

$331

Roundtrip

found 5 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $331 found 5 hours ago

Sat, Aug 23 - Thu, Aug 28

ORD

O'Hare Intl.

EYW

Key West Intl.

$337 Roundtrip, found 5 hours ago

$337

Roundtrip

found 5 hours ago

Select Delta flight, departing Sat, Aug 23 from O'Hare Intl. to Key West Intl., returning Thu, Aug 28, priced at $337 found 5 hours ago

Wed, Oct 15 - Sat, Oct 18

ORD

O'Hare Intl.

EYW

Key West Intl.

$340 Roundtrip, found 1 day ago

$340

Roundtrip

found 1 day ago

Select Delta flight, departing Wed, Oct 15 from O'Hare Intl. to Key West Intl., returning Sat, Oct 18, priced at $340 found 1 day ago

Thu, Aug 21 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$344 Roundtrip, found 5 hours ago

$344

Roundtrip

found 5 hours ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $344 found 5 hours ago

Thu, Aug 21 - Tue, Sep 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$344 Roundtrip, found 5 hours ago

$344

Roundtrip

found 5 hours ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Tue, Sep 2, priced at $344 found 5 hours ago

Thu, Aug 21 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$351 Roundtrip, found 5 hours ago

$351

Roundtrip

found 5 hours ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $351 found 5 hours ago

Thu, Aug 21 - Thu, Aug 28

ORD

O'Hare Intl.

EYW

Key West Intl.

$357 Roundtrip, found 5 hours ago

$357

Roundtrip

found 5 hours ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Thu, Aug 28, priced at $357 found 5 hours ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$358 Roundtrip, found 5 hours ago

$358

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $358 found 5 hours ago

Fri, Aug 22 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$366 Roundtrip, found 5 hours ago

$366

Roundtrip

found 5 hours ago

Select Delta flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $366 found 5 hours ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$367 Roundtrip, found 5 hours ago

$367

Roundtrip

found 5 hours ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $367 found 5 hours ago

Fri, Aug 22 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$373 Roundtrip, found 5 hours ago

$373

Roundtrip

found 5 hours ago

Select Delta flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $373 found 5 hours ago

Tue, Aug 26 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$377 Roundtrip, found 5 hours ago

$377

Roundtrip

found 5 hours ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $377 found 5 hours ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$391 Roundtrip, found 5 hours ago

$391

Roundtrip

found 5 hours ago

Select United flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $391 found 5 hours ago

Sun, Oct 12 - Thu, Oct 16

ORD

O'Hare Intl.

EYW

Key West Intl.

$482 Roundtrip, found 1 day ago

$482

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Sun, Oct 12 from O'Hare Intl. to Key West Intl., returning Thu, Oct 16, priced at $482 found 1 day ago