Flights from Key West to Chicago

Cheapest flights from Key West

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 12 - Tue, Aug 19

EYW

Key West Intl.

ORD

O'Hare Intl.

$269 Roundtrip, found 3 days ago

$269

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Aug 12 from Key West Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $269 found 3 days ago

Sat, Aug 9 - Tue, Aug 19

EYW

Key West Intl.

ORD

O'Hare Intl.

$289 Roundtrip, found 3 days ago

$289

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 9 from Key West Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $289 found 3 days ago

Wed, Jul 9 - Wed, Jul 16

EYW

Key West Intl.

ORD

O'Hare Intl.

$305 Roundtrip, found 6 days ago

$305

Roundtrip

found 6 days ago

Select United flight, departing Wed, Jul 9 from Key West Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $305 found 6 days ago

Sat, Aug 9 - Thu, Aug 14

EYW

Key West Intl.

ORD

O'Hare Intl.

$309 Roundtrip, found 3 days ago

$309

Roundtrip

found 3 days ago

Select Delta flight, departing Sat, Aug 9 from Key West Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $309 found 3 days ago

Wed, Jul 9 - Sat, Jul 12

EYW

Key West Intl.

ORD

O'Hare Intl.

$320 Roundtrip, found 6 days ago

$320

Roundtrip

found 6 days ago

Select Delta flight, departing Wed, Jul 9 from Key West Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $320 found 6 days ago

Wed, Jul 9 - Wed, Jul 16

EYW

Key West Intl.

ORD

O'Hare Intl.

$323 Roundtrip, found 6 days ago

$323

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Jul 9 from Key West Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $323 found 6 days ago

Fri, Jul 4 - Tue, Jul 15

EYW

Key West Intl.

ORD

O'Hare Intl.

$324 Roundtrip, found 6 days ago

$324

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 4 from Key West Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $324 found 6 days ago

Mon, Aug 11 - Tue, Aug 19

EYW

Key West Intl.

ORD

O'Hare Intl.

$324 Roundtrip, found 3 days ago

$324

Roundtrip

found 3 days ago

Select United flight, departing Mon, Aug 11 from Key West Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $324 found 3 days ago

Mon, Aug 11 - Thu, Aug 14

EYW

Key West Intl.

ORD

O'Hare Intl.

$328 Roundtrip, found 3 days ago

$328

Roundtrip

found 3 days ago

Select United flight, departing Mon, Aug 11 from Key West Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $328 found 3 days ago

Tue, Aug 12 - Fri, Aug 15

EYW

Key West Intl.

ORD

O'Hare Intl.

$331 Roundtrip, found 3 days ago

$331

Roundtrip

found 3 days ago

Select Delta flight, departing Tue, Aug 12 from Key West Intl. to O'Hare Intl., returning Fri, Aug 15, priced at $331 found 3 days ago

Tue, Jul 8 - Tue, Jul 15

EYW

Key West Intl.

ORD

O'Hare Intl.

$337 Roundtrip, found 6 days ago

$337

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 8 from Key West Intl. to O'Hare Intl., returning Tue, Jul 15, priced at $337 found 6 days ago

Fri, Jul 4 - Mon, Jul 14

EYW

Key West Intl.

ORD

O'Hare Intl.

$344 Roundtrip, found 6 days ago

$344

Roundtrip

found 6 days ago

Select Delta flight, departing Fri, Jul 4 from Key West Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $344 found 6 days ago

Wed, Jul 9 - Wed, Jul 16

EYW

Key West Intl.

ORD

O'Hare Intl.

$347 Roundtrip, found 6 days ago

$347

Roundtrip

found 6 days ago

Select American Airlines flight, departing Wed, Jul 9 from Key West Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $347 found 6 days ago

Mon, Jul 7 - Wed, Jul 16

EYW

Key West Intl.

ORD

O'Hare Intl.

$348 Roundtrip, found 6 days ago

$348

Roundtrip

found 6 days ago

Select American Airlines flight, departing Mon, Jul 7 from Key West Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $348 found 6 days ago

Mon, Aug 11 - Sun, Aug 17

EYW

Key West Intl.

ORD

O'Hare Intl.

$349 Roundtrip, found 3 days ago

$349

Roundtrip

found 3 days ago

Select United flight, departing Mon, Aug 11 from Key West Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $349 found 3 days ago

Thu, Jul 3 - Sat, Jul 12

EYW

Key West Intl.

ORD

O'Hare Intl.

$353 Roundtrip, found 6 days ago

$353

Roundtrip

found 6 days ago

Select United flight, departing Thu, Jul 3 from Key West Intl. to O'Hare Intl., returning Sat, Jul 12, priced at $353 found 6 days ago

Mon, Aug 11 - Fri, Aug 15

EYW

Key West Intl.

ORD

O'Hare Intl.

$355 Roundtrip, found 3 days ago

$355

Roundtrip

found 3 days ago

Select United flight, departing Mon, Aug 11 from Key West Intl. to O'Hare Intl., returning Fri, Aug 15, priced at $355 found 3 days ago

Tue, Jul 8 - Mon, Jul 14

EYW

Key West Intl.

ORD

O'Hare Intl.

$357 Roundtrip, found 6 days ago

$357

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Jul 8 from Key West Intl. to O'Hare Intl., returning Mon, Jul 14, priced at $357 found 6 days ago

Wed, Aug 13 - Thu, Aug 14

EYW

Key West Intl.

ORD

O'Hare Intl.

$357 Roundtrip, found 3 days ago

$357

Roundtrip

found 3 days ago

Select United flight, departing Wed, Aug 13 from Key West Intl. to O'Hare Intl., returning Thu, Aug 14, priced at $357 found 3 days ago

Sun, Aug 10 - Sun, Aug 17

EYW

Key West Intl.

ORD

O'Hare Intl.

$363 Roundtrip, found 3 days ago

$363

Roundtrip

found 3 days ago

Select Delta flight, departing Sun, Aug 10 from Key West Intl. to O'Hare Intl., returning Sun, Aug 17, priced at $363 found 3 days ago