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.

Sat, Jun 7 - Wed, Jun 11

ORD

O'Hare Intl.

EYW

Key West Intl.

$323 Roundtrip, found 17 hours ago

$323

Roundtrip

found 17 hours ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Wed, Jun 11, priced at $323 found 17 hours ago

Sat, Jun 7 - Thu, Jun 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$326 Roundtrip, found 17 hours ago

$326

Roundtrip

found 17 hours ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Thu, Jun 12, priced at $326 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$357 Roundtrip, found 17 hours ago

$357

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $357 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$383 Roundtrip, found 17 hours ago

$383

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $383 found 17 hours ago

Sat, Jun 7 - Fri, Jun 13

ORD

O'Hare Intl.

EYW

Key West Intl.

$385 Roundtrip, found 17 hours ago

$385

Roundtrip

found 17 hours ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Fri, Jun 13, priced at $385 found 17 hours ago

Fri, Jun 6 - Thu, Jun 12

ORD

O'Hare Intl.

EYW

Key West Intl.

$388 Roundtrip, found 17 hours ago

$388

Roundtrip

found 17 hours ago

Select Delta flight, departing Fri, Jun 6 from O'Hare Intl. to Key West Intl., returning Thu, Jun 12, priced at $388 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$388 Roundtrip, found 17 hours ago

$388

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $388 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$392 Roundtrip, found 17 hours ago

$392

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $392 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$396 Roundtrip, found 17 hours ago

$396

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $396 found 17 hours ago

Wed, Jun 11 - Tue, Jun 17

ORD

O'Hare Intl.

EYW

Key West Intl.

$402 Roundtrip, found 17 hours ago

$402

Roundtrip

found 17 hours ago

Select United flight, departing Wed, Jun 11 from O'Hare Intl. to Key West Intl., returning Tue, Jun 17, priced at $402 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$405 Roundtrip, found 17 hours ago

$405

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $405 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$408 Roundtrip, found 17 hours ago

$408

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $408 found 17 hours ago

Thu, Jun 12 - Tue, Jun 17

ORD

O'Hare Intl.

EYW

Key West Intl.

$417 Roundtrip, found 17 hours ago

$417

Roundtrip

found 17 hours ago

Select United flight, departing Thu, Jun 12 from O'Hare Intl. to Key West Intl., returning Tue, Jun 17, priced at $417 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$421 Roundtrip, found 17 hours ago

$421

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $421 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$422 Roundtrip, found 17 hours ago

$422

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $422 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$423 Roundtrip, found 17 hours ago

$423

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $423 found 17 hours ago

Sat, Jun 7 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$427 Roundtrip, found 17 hours ago

$427

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $427 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$427 Roundtrip, found 17 hours ago

$427

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $427 found 17 hours ago

Mon, Jun 9 - Sat, Jun 14

ORD

O'Hare Intl.

EYW

Key West Intl.

$431 Roundtrip, found 17 hours ago

$431

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Mon, Jun 9 from O'Hare Intl. to Key West Intl., returning Sat, Jun 14, priced at $431 found 17 hours ago

Sat, Jun 7 - Mon, Jun 16

ORD

O'Hare Intl.

EYW

Key West Intl.

$434 Roundtrip, found 17 hours ago

$434

Roundtrip

found 17 hours ago

Select Delta flight, departing Sat, Jun 7 from O'Hare Intl. to Key West Intl., returning Mon, Jun 16, priced at $434 found 17 hours ago