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.

Tue, Nov 4 - Sat, Nov 8

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$356 Roundtrip, found 3 hours ago

$356

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Nov 8, priced at $356 found 3 hours ago

Fri, Nov 7 - Wed, Nov 12

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$363 Roundtrip, found 3 hours ago

$363

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Fri, Nov 7 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Nov 12, priced at $363 found 3 hours ago

Mon, Nov 3 - Sat, Nov 8

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$365 Roundtrip, found 3 hours ago

$365

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Nov 8, priced at $365 found 3 hours ago

Tue, Aug 19 - Fri, Aug 22

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$365 Roundtrip, found 2 days ago

$365

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Tue, Aug 19 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Aug 22, priced at $365 found 2 days ago

Thu, Aug 21 - Sat, Aug 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$367 Roundtrip, found 2 days ago

$367

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Aug 23, priced at $367 found 2 days ago

Tue, Nov 4 - Tue, Nov 11

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$372 Roundtrip, found 3 hours ago

$372

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Nov 11, priced at $372 found 3 hours ago

Mon, Aug 18 - Fri, Aug 22

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$374 Roundtrip, found 2 days ago

$374

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Mon, Aug 18 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Aug 22, priced at $374 found 2 days ago

Thu, Aug 21 - Sun, Aug 24

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$376 Roundtrip, found 2 days ago

$376

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Thu, Aug 21 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sun, Aug 24, priced at $376 found 2 days ago

Fri, Nov 7 - Tue, Nov 11

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$379 Roundtrip, found 3 hours ago

$379

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Fri, Nov 7 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Nov 11, priced at $379 found 3 hours ago

Tue, Nov 4 - Fri, Nov 7

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$381 Roundtrip, found 3 hours ago

$381

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Tue, Nov 4 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Nov 7, priced at $381 found 3 hours ago

Wed, Aug 20 - Sun, Aug 24

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$387 Roundtrip, found 2 days ago

$387

Roundtrip

found 2 days ago

Select Spirit Airlines flight, departing Wed, Aug 20 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sun, Aug 24, priced at $387 found 2 days ago

Mon, Nov 3 - Fri, Nov 7

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$390 Roundtrip, found 3 hours ago

$390

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Mon, Nov 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Nov 7, priced at $390 found 3 hours ago

Wed, Nov 5 - Fri, Nov 7

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$397 Roundtrip, found 3 hours ago

$397

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Wed, Nov 5 from O'Hare Intl. to Sir Donald Sangster Intl., returning Fri, Nov 7, priced at $397 found 3 hours ago

Thu, Nov 6 - Sat, Nov 8

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$403 Roundtrip, found 3 hours ago

$403

Roundtrip

found 3 hours ago

Select Frontier Airlines flight, departing Thu, Nov 6 from Midway Intl. to Sir Donald Sangster Intl., returning Sat, Nov 8, priced at $403 found 3 hours ago

Tue, Aug 5 - Sat, Aug 9

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$404 Roundtrip, found 3 days ago

$404

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Aug 5 from Midway Intl. to Sir Donald Sangster Intl., returning Sat, Aug 9, priced at $404 found 3 days ago

Tue, Aug 5 - Fri, Aug 8

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$406 Roundtrip, found 3 days ago

$406

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Tue, Aug 5 from Midway Intl. to Sir Donald Sangster Intl., returning Fri, Aug 8, priced at $406 found 3 days ago

Wed, Aug 6 - Sat, Aug 9

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$407 Roundtrip, found 3 days ago

$407

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Wed, Aug 6 from Midway Intl. to Sir Donald Sangster Intl., returning Sat, Aug 9, priced at $407 found 3 days ago

Wed, Aug 6 - Fri, Aug 8

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$409 Roundtrip, found 3 days ago

$409

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Wed, Aug 6 from Midway Intl. to Sir Donald Sangster Intl., returning Fri, Aug 8, priced at $409 found 3 days ago

Fri, Nov 7 - Sat, Nov 8

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$411 Roundtrip, found 3 hours ago

$411

Roundtrip

found 3 hours ago

Select Spirit Airlines flight, departing Fri, Nov 7 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Nov 8, priced at $411 found 3 hours ago

Mon, Nov 3 - Thu, Nov 13

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$453 Roundtrip, found 3 hours ago

$453

Roundtrip

found 3 hours ago

Select JetBlue Airways flight, departing Mon, Nov 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Nov 13, priced at $453 found 3 hours ago