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, Sep 4 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$240 Roundtrip, found 15 hours ago

$240

Roundtrip

found 15 hours ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $240 found 15 hours ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$254 Roundtrip, found 3 days ago

$254

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $254 found 3 days ago

Sat, Aug 30 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$255 Roundtrip, found 3 days ago

$255

Roundtrip

found 3 days 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 3 days ago

Sat, Aug 30 - Fri, Sep 5

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$256 Roundtrip, found 3 days ago

$256

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Aug 30 from Luis Munoz Marin Intl. to O'Hare Intl., returning Fri, Sep 5, priced at $256 found 3 days ago

Thu, Sep 4 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$258 Roundtrip, found 15 hours ago

$258

Roundtrip

found 15 hours ago

Select Frontier Airlines flight, departing Thu, Sep 4 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $258 found 15 hours ago

Sat, Aug 30 - Thu, Sep 4

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$275 Roundtrip, found 3 days ago

$275

Roundtrip

found 3 days ago

Select Frontier Airlines flight, departing Sat, Aug 30 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $275 found 3 days ago

Mon, Aug 25 - Thu, Sep 4

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$276 Roundtrip, found 3 days ago

$276

Roundtrip

found 3 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 $276 found 3 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$280 Roundtrip, found 3 days ago

$280

Roundtrip

found 3 days 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 3 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$287 Roundtrip, found 3 days ago

$287

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $287 found 3 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$288 Roundtrip, found 3 days ago

$288

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $288 found 3 days ago

Mon, Sep 1 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$294 Roundtrip, found 15 hours ago

$294

Roundtrip

found 15 hours 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 15 hours ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$299 Roundtrip, found 3 days ago

$299

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $299 found 3 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$301 Roundtrip, found 3 days ago

$301

Roundtrip

found 3 days ago

Select Spirit Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $301 found 3 days ago

Thu, Jun 5 - Tue, Jun 10

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$301 Roundtrip, found 1 day ago

$301

Roundtrip

found 1 day ago

Select Frontier Airlines flight, departing Thu, Jun 5 from Luis Munoz Marin Intl. to O'Hare Intl., returning Tue, Jun 10, priced at $301 found 1 day ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$305 Roundtrip, found 3 days ago

$305

Roundtrip

found 3 days ago

Select United flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $305 found 3 days ago

Mon, Sep 1 - Thu, Sep 11

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$312 Roundtrip, found 15 hours ago

$312

Roundtrip

found 15 hours ago

Select Frontier Airlines flight, departing Mon, Sep 1 from Luis Munoz Marin Intl. to O'Hare Intl., returning Thu, Sep 11, priced at $312 found 15 hours ago

Fri, Sep 5 - Tue, Sep 9

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$321 Roundtrip, found 15 hours ago

$321

Roundtrip

found 15 hours 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 15 hours ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$341 Roundtrip, found 3 days ago

$341

Roundtrip

found 3 days ago

Select United flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $341 found 3 days ago

Wed, Aug 27 - Sun, Sep 7

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$357 Roundtrip, found 3 days ago

$357

Roundtrip

found 3 days ago

Select American Airlines flight, departing Wed, Aug 27 from Luis Munoz Marin Intl. to O'Hare Intl., returning Sun, Sep 7, priced at $357 found 3 days ago

Sun, Aug 31 - Tue, Sep 9

SJU

Luis Munoz Marin Intl.

ORD

O'Hare Intl.

$438 Roundtrip, found 3 days ago

$438

Roundtrip

found 3 days ago

Select JetBlue Airways flight, departing Sun, Aug 31 from Luis Munoz Marin Intl. to O'Hare Intl., returning Tue, Sep 9, priced at $438 found 3 days ago