Flights from Chicago to Lower Keys

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 1 day ago

$269

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $269 found 1 day ago

Thu, Aug 21 - Wed, Sep 3

ORD

O'Hare Intl.

EYW

Key West Intl.

$289 Roundtrip, found 1 day ago

$289

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Wed, Sep 3, priced at $289 found 1 day ago

Fri, Aug 22 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$324 Roundtrip, found 1 day ago

$324

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $324 found 1 day ago

Thu, Aug 21 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$344 Roundtrip, found 1 day ago

$344

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $344 found 1 day ago

Fri, Aug 22 - Thu, Aug 28

ORD

O'Hare Intl.

EYW

Key West Intl.

$384 Roundtrip, found 1 day ago

$384

Roundtrip

found 1 day ago

Select Delta flight, departing Fri, Aug 22 from O'Hare Intl. to Key West Intl., returning Thu, Aug 28, priced at $384 found 1 day ago

Tue, Aug 26 - Tue, Sep 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$389 Roundtrip, found 1 day ago

$389

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Tue, Sep 2, priced at $389 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$397 Roundtrip, found 1 day ago

$397

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $397 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$404 Roundtrip, found 1 day ago

$404

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $404 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$407 Roundtrip, found 1 day ago

$407

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $407 found 1 day ago

Thu, Aug 21 - Tue, Sep 2

ORD

O'Hare Intl.

EYW

Key West Intl.

$409 Roundtrip, found 1 day ago

$409

Roundtrip

found 1 day ago

Select Delta flight, departing Thu, Aug 21 from O'Hare Intl. to Key West Intl., returning Tue, Sep 2, priced at $409 found 1 day ago

Tue, Aug 26 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$413 Roundtrip, found 1 day ago

$413

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Aug 26 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $413 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$419 Roundtrip, found 1 day ago

$419

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $419 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$431 Roundtrip, found 1 day ago

$431

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $431 found 1 day ago

Sun, Aug 24 - Fri, Aug 29

ORD

O'Hare Intl.

EYW

Key West Intl.

$433 Roundtrip, found 1 day ago

$433

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Fri, Aug 29, priced at $433 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$439 Roundtrip, found 1 day ago

$439

Roundtrip

found 1 day ago

Select Delta flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $439 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$444 Roundtrip, found 1 day ago

$444

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $444 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$451 Roundtrip, found 1 day ago

$451

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $451 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$454 Roundtrip, found 1 day ago

$454

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $454 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$461 Roundtrip, found 1 day ago

$461

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $461 found 1 day ago

Sun, Aug 24 - Sun, Aug 31

ORD

O'Hare Intl.

EYW

Key West Intl.

$710 Roundtrip, found 1 day ago

$710

Roundtrip

found 1 day ago

Select United flight, departing Sun, Aug 24 from O'Hare Intl. to Key West Intl., returning Sun, Aug 31, priced at $710 found 1 day ago