Cheap flights from Chicago to Calle 25 de Enero

View AU$496 flight on Sat, 2 Aug. 2025Opens in a new window

Popular airlines from Chicago to Calle 25 de Enero

  • Jetstar

    Jetstar

  • Qantas Airways

    Qantas Airways

  • Virgin Australia

    Virgin Australia

  • Scoot

    Scoot

  • American Airlines

    American Airlines

  • Emirates

    Emirates

  • United

    United

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Cheap Flights from Chicago (CHI) to Calle 25 de Enero (SJU)

Prices were available within the past 7 days for one-way flights and round trip tickets for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$817 Return, found 18 hours ago
AU$817
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$817 found 18 hours ago
American Airlines
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$868 Return, found 18 hours ago
AU$868
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$868 found 18 hours ago
American Airlines
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$877 Return, found 18 hours ago
AU$877
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$877 found 18 hours ago
American Airlines
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$923 Return, found 18 hours ago
AU$923
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$923 found 18 hours ago
United
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$1,052 Return, found 18 hours ago
AU$1,052
Return
found 18 hours ago
Select United flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$1,052 found 18 hours ago
Delta
Sat, 2 Aug. - Sat, 9 Aug.
ORD
Chicago
SJU
San Juan
AU$1,507 Return, found 18 hours ago
AU$1,507
Return
found 18 hours ago
Select Delta flight, departing Sat, 2 Aug. from Chicago to San Juan, returning Sat, 9 Aug., priced at AU$1,507 found 18 hours ago

Find the cheapest month to fly from Chicago (CHI) to San Juan (SJU)

January is typically the cheapest month to fly

From AU$193 - AU$656 per traveller.

Graph displaying average flight prices per month

*Available to Expedia members.