Flights from Chicago to Juana Diaz

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.

Mon, Oct 6 - Sat, Oct 11

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$240 Roundtrip, found 1 day ago

$240

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Oct 6 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Oct 11, priced at $240 found 1 day ago

Sun, Oct 12 - Fri, Oct 17

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$240 Roundtrip, just found

$240

Roundtrip

just found

Select Frontier Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Oct 17, priced at $240 just found

Mon, Jul 14 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$246 Roundtrip, found 14 hours ago

$246

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $246 found 14 hours ago

Sun, Oct 12 - Sat, Oct 18

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$248 Roundtrip, just found

$248

Roundtrip

just found

Select Frontier Airlines flight, departing Sun, Oct 12 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Oct 18, priced at $248 just found

Sat, Jul 12 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$251 Roundtrip, found 14 hours ago

$251

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $251 found 14 hours ago

Sat, Oct 11 - Sat, Oct 11

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$253 Roundtrip, found 1 day ago

$253

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Oct 11 from Midway Intl. to Luis Munoz Marin Intl., returning Sat, Oct 11, priced at $253 found 1 day ago

Sun, Aug 17 - Thu, Aug 21

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$254 Roundtrip, found 1 day ago

$254

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sun, Aug 17 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Aug 21, priced at $254 found 1 day ago

Mon, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$257 Roundtrip, found 6 days ago

$257

Roundtrip

found 6 days ago

Select Frontier Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $257 found 6 days ago

Fri, Oct 10 - Fri, Oct 17

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$258 Roundtrip, just found

$258

Roundtrip

just found

Select Frontier Airlines flight, departing Fri, Oct 10 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Oct 17, priced at $258 just found

Mon, Jul 14 - Thu, Jul 17

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$260 Roundtrip, found 14 hours ago

$260

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Jul 17, priced at $260 found 14 hours ago

Fri, Jul 11 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$260 Roundtrip, found 14 hours ago

$260

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $260 found 14 hours ago

Thu, Oct 9 - Thu, Oct 9

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$262 Roundtrip, found 1 day ago

$262

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Oct 9 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Oct 9, priced at $262 found 1 day ago

Thu, Jul 10 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$263 Roundtrip, found 14 hours ago

$263

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Thu, Jul 10 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $263 found 14 hours ago

Sat, Jul 12 - Thu, Jul 17

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$265 Roundtrip, found 14 hours ago

$265

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Sat, Jul 12 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Jul 17, priced at $265 found 14 hours ago

Mon, Jul 14 - Wed, Jul 16

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$266 Roundtrip, found 14 hours ago

$266

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Mon, Jul 14 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Jul 16, priced at $266 found 14 hours ago

Fri, Jul 11 - Fri, Jul 18

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$288 Roundtrip, found 14 hours ago

$288

Roundtrip

found 14 hours ago

Select Spirit Airlines flight, departing Fri, Jul 11 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Jul 18, priced at $288 found 14 hours ago

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$297 Roundtrip, found 1 day ago

$297

Roundtrip

found 1 day ago

Select JetBlue Airways flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Oct 15, priced at $297 found 1 day ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$322 Roundtrip, just found

$322

Roundtrip

just found

Select United flight, departing Sat, Oct 11 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Oct 18, priced at $322 just found

Tue, Oct 7 - Wed, Oct 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$331 Roundtrip, found 1 day ago

$331

Roundtrip

found 1 day ago

Select Delta flight, departing Tue, Oct 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Oct 15, priced at $331 found 1 day ago

Sat, Oct 11 - Sat, Oct 18

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$352 Roundtrip, just found

$352

Roundtrip

just found

Select American Airlines flight, departing Sat, Oct 11 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Oct 18, priced at $352 just found