Flights from Chicago to San Juan (Puerto Rico) with American Airlines

Our cheapest offers for flights from Chicago to San Juan (Puerto Rico)

Here you can compare cheap flights from Chicago (CHI) to San Juan (Puerto Rico) (SJU) for one-way or return trips. The following offers were searched for and found on idealo during the last few days. Or start your own flight search to San Juan (Puerto Rico). Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
2 Stopovers (PHL, CLT)
AA0471, AA3012, AA2199
12h 25min
Return
10/26/25
2 Stopovers (CLT, LGA)
AA0783, AA2031, AA0462
16h 46min
American Airlines ?
$501
found 3 days ago
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
1 Stopover (MIA)
AA0534, AA0967
08h 54min
Return
10/26/25
1 Stopover (PHL)
AA1147, AA1854
07h 34min
American Airlines ?
$520
found 3 days ago
Chicago
San Juan (Puerto Rico)
Outbound
10/24/25
1 Stopover (MIA)
AA0534, AA0967
08h 54min
Return
10/26/25
1 Stopover (PHL)
AA1147, AA1854
07h 34min
American Airlines ?
$661
found 3 days ago
Chicago
San Juan (Puerto Rico)
Outbound
12/26/25
2 Stopovers (CLT, MIA)
AA1606, AA2076, AA0342
19h 55min
Return
01/01/26
1 Stopover (PHL)
AA0419, AA1937
13h 53min
American Airlines ?
$729
Chicago
San Juan (Puerto Rico)
Outbound
12/26/25
1 Stopover (PHL)
AA1854, AA1474
15h 09min
Return
01/01/26
1 Stopover (PHL)
AA0419, AA1937
13h 53min
American Airlines ?
$815
Prices based on recent searches, subject to last-minute changes
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Important flight information

Flight information: Chicago - San Juan (Puerto Rico)

Roundtrip from 260,93 USD
Flight duration min. 04:30 / max. 07:00
Return flight duration min. 05:10/ max. 06:05
Distance 3318 km
Flights per week 28
Departure airport Airport Chicago-IL, all airports (CHI)
Arrival airport Airport San Juan - Luis Muñoz Marín International Airport (SJU)
Destination country Flights to Puerto Rico
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