Cheap Flights from Chicago to San Juan

View €144 flight on Tue, 20 May 2025Opens in a new window

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Cheap flights from Chicago to San Juan (CHI-SJU)

Prices were available within the past 7 days and start at €144 for one-way flights and €352 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

JetBlue Airways
Tue, 20 May - Wed, 30 Jul
ORD
Chicago
SJU
San Juan
€352 Return, found 8 hours ago
€352
Return
found 8 hours ago
Select JetBlue Airways flight, departing Tue, 20 May from Chicago to San Juan, returning Wed, 30 Jul, priced at €352 found 8 hours ago
JetBlue Airways
Tue, 20 May - Wed, 30 Jul
ORD
Chicago
SJU
San Juan
€366 Return, found 8 hours ago
€366
Return
found 8 hours ago
Select JetBlue Airways flight, departing Tue, 20 May from Chicago to San Juan, returning Wed, 30 Jul, priced at €366 found 8 hours ago
JetBlue Airways
Tue, 20 May - Wed, 30 Jul
ORD
Chicago
SJU
San Juan
€371 Return, found 8 hours ago
€371
Return
found 8 hours ago
Select JetBlue Airways flight, departing Tue, 20 May from Chicago to San Juan, returning Wed, 30 Jul, priced at €371 found 8 hours ago
United
Mon, 7 Jul - Thu, 10 Jul
ORD
Chicago
SJU
San Juan
€377 Return, found 1 day ago
€377
Return
found 1 day ago
Select United flight, departing Mon, 7 Jul from Chicago to San Juan, returning Thu, 10 Jul, priced at €377 found 1 day ago
American Airlines
Tue, 20 May - Wed, 30 Jul
ORD
Chicago
SJU
San Juan
€384 Return, found 8 hours ago
€384
Return
found 8 hours ago
Select American Airlines flight, departing Tue, 20 May from Chicago to San Juan, returning Wed, 30 Jul, priced at €384 found 8 hours ago
Delta
Tue, 20 May - Wed, 30 Jul
ORD
Chicago
SJU
San Juan
€396 Return, found 8 hours ago
€396
Return
found 8 hours ago
Select Delta flight, departing Tue, 20 May from Chicago to San Juan, returning Wed, 30 Jul, priced at €396 found 8 hours ago
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