Flights from San Juan to Chicago

Cheapest flights from San Juan

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, Sep 7 - Sat, Sep 27

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 20 hours ago

$240

Roundtrip

found 20 hours ago

Select Frontier Airlines flight, departing Sun, Sep 7 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $240 found 20 hours ago

Sat, Aug 30 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 1 day ago

$255

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 30 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $255 found 1 day ago

Sat, Aug 30 - Sat, Sep 6

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 1 day ago

$256

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 30 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $256 found 1 day ago

Mon, Sep 8 - Sat, Sep 27

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$258 Roundtrip, found 20 hours ago

$258

Roundtrip

found 20 hours ago

Select Frontier Airlines flight, departing Mon, Sep 8 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sat, Sep 27, priced at $258 found 20 hours ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$259 Roundtrip, found 1 day ago

$259

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $259 found 1 day ago

Sat, Jun 14 - Sun, Jun 29

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$270 Roundtrip, found 1 day ago

$270

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 14 from Luis Munoz Marin Intl. to Midway Intl., returning Sun, Jun 29, priced at $270 found 1 day ago

Mon, Aug 25 - Fri, Sep 5

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$274 Roundtrip, found 1 day ago

$274

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Aug 25 from Luis Munoz Marin Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $274 found 1 day ago

Sat, Jun 14 - Mon, Jun 30

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$274 Roundtrip, found 1 day ago

$274

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 14 from Luis Munoz Marin Intl. to Midway Intl., returning Mon, Jun 30, priced at $274 found 1 day ago

Sat, Aug 30 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$275 Roundtrip, found 1 day ago

$275

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Aug 30 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $275 found 1 day ago

Mon, Aug 25 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 1 day ago

$276

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Mon, Aug 25 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $276 found 1 day ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$280 Roundtrip, found 1 day ago

$280

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $280 found 1 day ago

Sat, Jun 14 - Thu, Jun 26

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$291 Roundtrip, found 1 day ago

$291

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Sat, Jun 14 from Luis Munoz Marin Intl. to Midway Intl., returning Thu, Jun 26, priced at $291 found 1 day ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$292 Roundtrip, found 1 day ago

$292

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $292 found 1 day ago

Mon, Sep 1 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$294 Roundtrip, found 2 days ago

$294

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Sep 1 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $294 found 2 days ago

Thu, Jun 12 - Sun, Jun 29

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$297 Roundtrip, found 1 day ago

$297

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jun 12 from Luis Munoz Marin Intl. to Midway Intl., returning Sun, Jun 29, priced at $297 found 1 day ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$298 Roundtrip, found 1 day ago

$298

Roundtrip

found 1 day ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $298 found 1 day ago

Fri, Sep 5 - Tue, Sep 9

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$321 Roundtrip, found 2 days ago

$321

Roundtrip

found 2 days ago

Select Delta flight, departing Fri, Sep 5 from Luis Munoz Marin Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $321 found 2 days ago

Fri, Sep 12 - Tue, Sep 23

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$334 Roundtrip, found 20 hours ago

$334

Roundtrip

found 20 hours ago

Select JetBlue Airways flight, departing Fri, Sep 12 from Luis Munoz Marin Intl. to O'Hare Intl., returning Tue, Sep 23, priced at $334 found 20 hours ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$365 Roundtrip, found 1 day ago

$365

Roundtrip

found 1 day ago

Select American Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $365 found 1 day ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$404 Roundtrip, found 1 day ago

$404

Roundtrip

found 1 day ago

Select United flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $404 found 1 day ago