Flights from Chicago to Oracabessa

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.

Sun, Oct 12 - Fri, Oct 17

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$387 Roundtrip, found 23 hours ago

$387

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sun, Oct 12 from Midway Intl. to Sir Donald Sangster Intl., returning Fri, Oct 17, priced at $387 found 23 hours ago

Sat, Aug 2 - Sat, Aug 9

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$391 Roundtrip, found 3 days ago

$391

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Sir Donald Sangster Intl., returning Sat, Aug 9, priced at $391 found 3 days ago

Sun, Aug 3 - Wed, Aug 6

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$391 Roundtrip, found 3 days ago

$391

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Aug 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Aug 6, priced at $391 found 3 days ago

Wed, Oct 15 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$392 Roundtrip, found 23 hours ago

$392

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $392 found 23 hours ago

Sat, Aug 2 - Tue, Aug 5

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$398 Roundtrip, found 3 days ago

$398

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Aug 2 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Aug 5, priced at $398 found 3 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$401 Roundtrip, found 1 day ago

$401

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $401 found 1 day ago

Sun, Oct 12 - Sun, Oct 19

MDW

Midway Intl.

MBJ

Sir Donald Sangster Intl.

$403 Roundtrip, found 23 hours ago

$403

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sun, Oct 12 from Midway Intl. to Sir Donald Sangster Intl., returning Sun, Oct 19, priced at $403 found 23 hours ago

Sun, Aug 3 - Wed, Aug 6

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$405 Roundtrip, found 3 days ago

$405

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sun, Aug 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Aug 6, priced at $405 found 3 days ago

Tue, Aug 5 - Wed, Aug 6

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 Wed, Aug 6, priced at $406 found 3 days ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$406 Roundtrip, found 2 days ago

$406

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $406 found 2 days ago

Thu, Jul 31 - Tue, Aug 5

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$408 Roundtrip, found 3 days ago

$408

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Thu, Jul 31 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Aug 5, priced at $408 found 3 days ago

Wed, Oct 15 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$409 Roundtrip, found 23 hours ago

$409

Roundtrip

found 23 hours 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 23 hours ago

Sat, Oct 18 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$410 Roundtrip, found 23 hours ago

$410

Roundtrip

found 23 hours ago

Select Frontier Airlines flight, departing Sat, Oct 18 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $410 found 23 hours ago

Tue, Oct 14 - Thu, Oct 23

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$491 Roundtrip, found 23 hours ago

$491

Roundtrip

found 23 hours ago

Select Delta flight, departing Tue, Oct 14 from O'Hare Intl. to Sir Donald Sangster Intl., returning Thu, Oct 23, priced at $491 found 23 hours ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$506 Roundtrip, found 1 day ago

$506

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $506 found 1 day ago

Mon, Oct 13 - Tue, Oct 21

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$546 Roundtrip, found 23 hours ago

$546

Roundtrip

found 23 hours ago

Select American Airlines flight, departing Mon, Oct 13 from O'Hare Intl. to Sir Donald Sangster Intl., returning Tue, Oct 21, priced at $546 found 23 hours ago

Sun, Aug 3 - Wed, Aug 6

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$576 Roundtrip, found 3 days ago

$576

Roundtrip

found 3 days ago

Select Air Canada flight, departing Sun, Aug 3 from O'Hare Intl. to Sir Donald Sangster Intl., returning Wed, Aug 6, priced at $576 found 3 days ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$743 Roundtrip, found 1 day ago

$743

Roundtrip

found 1 day ago

Select United flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $743 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$845 Roundtrip, found 1 day ago

$845

Roundtrip

found 1 day ago

Select Copa flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $845 found 1 day ago

Wed, Oct 15 - Mon, Oct 20

ORD

O'Hare Intl.

MBJ

Sir Donald Sangster Intl.

$1,022 Roundtrip, found 1 day ago

$1,022

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Wed, Oct 15 from O'Hare Intl. to Sir Donald Sangster Intl., returning Mon, Oct 20, priced at $1,022 found 1 day ago