Flights from Chicago to Montego Bay

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.

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$409 Roundtrip, found 1 day ago

$409

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Oct 21, priced at $409 found 1 day ago

Wed, Oct 15 - Sat, Oct 18

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$419 Roundtrip, found 1 day ago

$419

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Oct 18, priced at $419 found 1 day ago

Wed, Oct 15 - Fri, Oct 17

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$421 Roundtrip, found 1 day ago

$421

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Oct 17, priced at $421 found 1 day ago

Mon, Oct 13 - Wed, Oct 22

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$426 Roundtrip, found 1 day ago

$426

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Oct 22, priced at $426 found 1 day ago

Wed, Oct 15 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$429 Roundtrip, found 1 day ago

$429

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $429 found 1 day ago

Sun, Oct 19 - Wed, Oct 22

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$431 Roundtrip, found 1 day ago

$431

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Oct 22, priced at $431 found 1 day ago

Mon, Oct 13 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$436 Roundtrip, found 1 day ago

$436

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Oct 21, priced at $436 found 1 day ago

Thu, Oct 16 - Sat, Oct 18

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$439 Roundtrip, found 1 day ago

$439

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Oct 18, priced at $439 found 1 day ago

Sun, Oct 19 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$441 Roundtrip, found 1 day ago

$441

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Oct 21, priced at $441 found 1 day ago

Thu, Oct 16 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$449 Roundtrip, found 1 day ago

$449

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $449 found 1 day ago

Thu, Oct 16 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$451 Roundtrip, found 1 day ago

$451

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $451 found 1 day ago

Fri, Oct 17 - Wed, Oct 22

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$456 Roundtrip, found 1 day ago

$456

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Oct 22, priced at $456 found 1 day ago

Mon, Oct 13 - Sat, Oct 18

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$461 Roundtrip, found 1 day ago

$461

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Oct 18, priced at $461 found 1 day ago

Fri, Oct 17 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$466 Roundtrip, found 1 day ago

$466

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Oct 21, priced at $466 found 1 day ago

Mon, Oct 13 - Sun, Oct 19

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$466 Roundtrip, found 1 day ago

$466

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sun, Oct 19, priced at $466 found 1 day ago

Fri, Oct 17 - Sat, Oct 18

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$491 Roundtrip, found 1 day ago

$491

Roundtrip

found 1 day ago

Select American Airlines flight, departing Fri, Oct 17 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Oct 18, priced at $491 found 1 day ago

Sat, Oct 18 - Sun, Oct 19

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$496 Roundtrip, found 1 day ago

$496

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sun, Oct 19, priced at $496 found 1 day ago

Mon, Oct 13 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$517 Roundtrip, found 1 day ago

$517

Roundtrip

found 1 day ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $517 found 1 day ago

Thu, Oct 16 - Fri, Oct 17

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$522 Roundtrip, found 1 day ago

$522

Roundtrip

found 1 day ago

Select American Airlines flight, departing Thu, Oct 16 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Oct 17, priced at $522 found 1 day ago

Sun, Oct 19 - Sun, Oct 19

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$697 Roundtrip, found 1 day ago

$697

Roundtrip

found 1 day ago

Select American Airlines flight, departing Sun, Oct 19 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sun, Oct 19, priced at $697 found 1 day ago