Flights from Chicago to Puerto Rico

Our cheapest offers for flights from Chicago to Puerto Rico

Here you can compare cheap flights from Chicago (CHI) to Puerto Rico 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 Puerto Rico. Prices and availability may change at any time.

Outbound Return Airlines Shop Baggage Price
Chicago
San Juan (Puerto Rico)
Outbound
04/12/25
1 Stopover (MCO)
F93044, F91746
14h 58min
Return
04/27/25
direct
NK0264
05h 23min
Frontier Airlines ?
$195
Best option
Chicago
San Juan (Puerto Rico)
Outbound
06/08/25
direct
UA0695
04h 51min
Return
06/12/25
direct
UA2089
05h 10min
United Airlines ?
$424
Chicago
San Juan (Puerto Rico)
Outbound
04/21/25
2 Stopovers (ATL, MCO)
F91596, F94556, F94726
39h 29min
Return
05/19/25
2 Stopovers (BWI, ATL)
F92265, F92509, F91595
35h 43min
Frontier Airlines ?
$197
Prices based on recent searches, subject to last-minute changes
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