Flights from Chicago to Cayey

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, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$257 Roundtrip, found 4 days ago

$257

Roundtrip

found 4 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 4 days ago

Tue, Jul 8 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$259 Roundtrip, found 4 days ago

$259

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $259 found 4 days ago

Wed, Jul 16 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$266 Roundtrip, found 6 hours ago

$266

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $266 found 6 hours ago

Sun, Jul 13 - Thu, Aug 7

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$268 Roundtrip, found 6 hours ago

$268

Roundtrip

found 6 hours ago

Select Frontier Airlines flight, departing Sun, Jul 13 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $268 found 6 hours ago

Sat, Jul 5 - Thu, Jul 17

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$268 Roundtrip, found 4 days ago

$268

Roundtrip

found 4 days ago

Select Frontier Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Jul 17, priced at $268 found 4 days ago

Wed, Jul 16 - Fri, Aug 8

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$270 Roundtrip, found 6 hours ago

$270

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Wed, Jul 16 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Aug 8, priced at $270 found 6 hours ago

Tue, Jul 8 - Sat, Jul 12

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$270 Roundtrip, found 4 days ago

$270

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Tue, Jul 8 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sat, Jul 12, priced at $270 found 4 days ago

Tue, Jul 15 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$275 Roundtrip, found 6 hours ago

$275

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Jul 15 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $275 found 6 hours ago

Thu, Jul 17 - Thu, Aug 7

MDW

Midway Intl.

SJU

Luis Munoz Marin Intl.

$277 Roundtrip, found 6 hours ago

$277

Roundtrip

found 6 hours ago

Select Frontier Airlines flight, departing Thu, Jul 17 from Midway Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $277 found 6 hours ago

Tue, Jul 15 - Fri, Aug 8

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$279 Roundtrip, found 6 hours ago

$279

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Tue, Jul 15 from O'Hare Intl. to Luis Munoz Marin Intl., returning Fri, Aug 8, priced at $279 found 6 hours ago

Fri, Jul 18 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$285 Roundtrip, found 6 hours ago

$285

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $285 found 6 hours ago

Mon, Jul 28 - Thu, Aug 7

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$288 Roundtrip, found 1 day ago

$288

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Jul 28 from O'Hare Intl. to Luis Munoz Marin Intl., returning Thu, Aug 7, priced at $288 found 1 day ago

Fri, Jul 18 - Wed, Aug 13

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$288 Roundtrip, found 6 hours ago

$288

Roundtrip

found 6 hours ago

Select Spirit Airlines flight, departing Fri, Jul 18 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Aug 13, priced at $288 found 6 hours ago

Sat, Jul 5 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$289 Roundtrip, found 4 days ago

$289

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $289 found 4 days ago

Sun, Jul 6 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$293 Roundtrip, found 4 days ago

$293

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Sun, Jul 6 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $293 found 4 days ago

Mon, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$294 Roundtrip, found 4 days ago

$294

Roundtrip

found 4 days ago

Select Spirit Airlines flight, departing Mon, Jul 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $294 found 4 days ago

Thu, Nov 20 - Wed, Dec 3

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$334 Roundtrip, found 6 days ago

$334

Roundtrip

found 6 days ago

Select JetBlue Airways flight, departing Thu, Nov 20 from O'Hare Intl. to Luis Munoz Marin Intl., returning Wed, Dec 3, priced at $334 found 6 days ago

Mon, Jul 7 - Tue, Jul 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$339 Roundtrip, found 4 days ago

$339

Roundtrip

found 4 days ago

Select United flight, departing Mon, Jul 7 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Jul 15, priced at $339 found 4 days ago

Tue, Nov 18 - Tue, Dec 2

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$356 Roundtrip, found 6 days ago

$356

Roundtrip

found 6 days ago

Select Delta flight, departing Tue, Nov 18 from O'Hare Intl. to Luis Munoz Marin Intl., returning Tue, Dec 2, priced at $356 found 6 days ago

Sun, Feb 1 - Sun, Feb 15

ORD

O'Hare Intl.

SJU

Luis Munoz Marin Intl.

$387 Roundtrip, found 5 days ago

$387

Roundtrip

found 5 days ago

Select American Airlines flight, departing Sun, Feb 1 from O'Hare Intl. to Luis Munoz Marin Intl., returning Sun, Feb 15, priced at $387 found 5 days ago