Cheap Flights To San Juan 2025

Photo by Coby McNaughton

San Juan Flights as Low as $300

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.

Spirit Airlines
Tue, Jun 17 - Fri, Jun 20
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$300 Roundtrip, found 1 day ago
$300
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Fri, Jun 20, priced at $300 found 1 day ago
Spirit Airlines
Tue, Jun 17 - Tue, Jun 24
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$304 Roundtrip, found 1 day ago
$304
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Tue, Jun 24, priced at $304 found 1 day ago
Spirit Airlines
Tue, Jun 17 - Mon, Jun 23
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$314 Roundtrip, found 1 day ago
$314
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Mon, Jun 23, priced at $314 found 1 day ago
Spirit Airlines
Tue, Jun 17 - Thu, Jun 19
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$323 Roundtrip, found 1 day ago
$323
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jun 17 from O'Hare Intl. to Juan Santamaría Intl., returning Thu, Jun 19, priced at $323 found 1 day ago
Spirit Airlines
Sun, May 18 - Mon, May 26
SAN
San Diego Intl.
SJO
Juan Santamaría Intl.
$420 Roundtrip, found 19 hours ago
$420
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from San Diego Intl. to Juan Santamaría Intl., returning Mon, May 26, priced at $420 found 19 hours ago
avianca
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$448 Roundtrip, found 1 day ago
$448
Roundtrip
found 1 day ago
Select avianca flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $448 found 1 day ago
Frontier Airlines
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$482 Roundtrip, found 1 day ago
$482
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $482 found 1 day ago
Delta
Fri, May 16 - Fri, May 23
SAN
San Diego Intl.
SJO
Juan Santamaría Intl.
$498 Roundtrip, found 19 hours ago
$498
Roundtrip
found 19 hours ago
Select Delta flight, departing Fri, May 16 from San Diego Intl. to Juan Santamaría Intl., returning Fri, May 23, priced at $498 found 19 hours ago
United
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$539 Roundtrip, found 1 day ago
$539
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $539 found 1 day ago
Copa
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$548 Roundtrip, found 1 day ago
$548
Roundtrip
found 1 day ago
Select Copa flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $548 found 1 day ago
American Airlines
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$558 Roundtrip, found 1 day ago
$558
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $558 found 1 day ago
Alaska Airlines
Wed, May 21 - Wed, May 28
SAN
San Diego Intl.
SJO
Juan Santamaría Intl.
$580 Roundtrip, found 19 hours ago
$580
Roundtrip
found 19 hours ago
Select Alaska Airlines flight, departing Wed, May 21 from San Diego Intl. to Juan Santamaría Intl., returning Wed, May 28, priced at $580 found 19 hours ago
Air Canada
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$654 Roundtrip, found 1 day ago
$654
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $654 found 1 day ago
United
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$800 Roundtrip, found 1 day ago
$800
Roundtrip
found 1 day ago
Select United flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $800 found 1 day ago
JetBlue Airways
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$806 Roundtrip, found 1 day ago
$806
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $806 found 1 day ago
Aeromexico
Sat, Jun 14 - Sat, Jun 21
ORD
O'Hare Intl.
SJO
Juan Santamaría Intl.
$940 Roundtrip, found 1 day ago
$940
Roundtrip
found 1 day ago
Select Aeromexico flight, departing Sat, Jun 14 from O'Hare Intl. to Juan Santamaría Intl., returning Sat, Jun 21, priced at $940 found 1 day ago

Cheap San Juan Flights

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