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.

Thu, Aug 28 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 17 hours ago

$240

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $240 found 17 hours ago

Sat, Aug 30 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 17 hours ago

$255

Roundtrip

found 17 hours 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 17 hours ago

Sat, Aug 30 - Sat, Sep 6

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 17 hours ago

$256

Roundtrip

found 17 hours 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 17 hours ago

Thu, Aug 28 - Thu, Sep 4

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$258 Roundtrip, found 2 days ago

$258

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $258 found 2 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$259 Roundtrip, found 17 hours ago

$259

Roundtrip

found 17 hours 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 17 hours ago

Mon, Aug 25 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$267 Roundtrip, found 17 hours ago

$267

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Mon, Aug 25 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $267 found 17 hours ago

Sat, Jun 14 - Sun, Jun 29

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$270 Roundtrip, found 6 days ago

$270

Roundtrip

found 6 days 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 6 days ago

Mon, Aug 25 - Fri, Sep 5

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$274 Roundtrip, found 6 days ago

$274

Roundtrip

found 6 days 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 6 days ago

Thu, Aug 28 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$274 Roundtrip, found 17 hours ago

$274

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Thu, Aug 28 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $274 found 17 hours ago

Sat, Aug 30 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$275 Roundtrip, found 17 hours ago

$275

Roundtrip

found 17 hours 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 17 hours ago

Mon, Aug 25 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 6 days ago

$276

Roundtrip

found 6 days 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 6 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$280 Roundtrip, found 17 hours ago

$280

Roundtrip

found 17 hours 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 17 hours ago

Sun, Aug 31 - Fri, Sep 5

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$284 Roundtrip, found 17 hours ago

$284

Roundtrip

found 17 hours ago

Select Frontier Airlines flight, departing Sun, Aug 31 from Luis Munoz Marin Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $284 found 17 hours ago

Mon, Aug 25 - Thu, Sep 4

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$285 Roundtrip, found 2 days ago

$285

Roundtrip

found 2 days ago

Select Frontier Airlines flight, departing Mon, Aug 25 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $285 found 2 days ago

Sat, Jun 14 - Thu, Jun 26

SJU

Luis Munoz Marin Intl.

MDW

Midway Intl.

$291 Roundtrip, found 6 days ago

$291

Roundtrip

found 6 days 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 6 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$303 Roundtrip, found 17 hours ago

$303

Roundtrip

found 17 hours ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $303 found 17 hours ago

Fri, Sep 12 - Tue, Sep 23

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$334 Roundtrip, found 5 days ago

$334

Roundtrip

found 5 days 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 5 days ago

Thu, Sep 4 - Wed, Sep 10

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$341 Roundtrip, found 2 days ago

$341

Roundtrip

found 2 days ago

Select Delta flight, departing Thu, Sep 4 from Luis Munoz Marin Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $341 found 2 days ago

Thu, Sep 4 - Wed, Sep 10

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$363 Roundtrip, found 2 days ago

$363

Roundtrip

found 2 days ago

Select United flight, departing Thu, Sep 4 from Luis Munoz Marin Intl. to O'Hare Intl., returning Wed, Sep 10, priced at $363 found 2 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$404 Roundtrip, found 17 hours ago

$404

Roundtrip

found 17 hours ago

Select American Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $404 found 17 hours ago