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Cheap Flights From Chicago To Puerto Rico

Cheap flights from Chicago (CHI) to popular destinations in Puerto Rico (PR)

Aguadilla
Carrier Departure Date Return Date Lowest Price
Spirit Sep 25, 2017 Oct 7, 2017 $331
JetBlue Sep 22, 2017 Sep 25, 2017 $394
JetBlue Oct 24, 2017 Oct 30, 2017 $408
JetBlue Sep 21, 2017 Sep 25, 2017 $417
Spirit Jun 28, 2017 Jul 17, 2017 $421
JetBlue Sep 13, 2017 Sep 16, 2017 $433
JetBlue May 17, 2017 May 24, 2017 $445
JetBlue Sep 14, 2017 Sep 16, 2017 $446
JetBlue May 27, 2017 Jun 13, 2017 $449
Spirit Jun 17, 2017 Jul 1, 2017 $451

Cheap Last Minute Flights from Chicago to Puerto Rico Prices shown were found by travelers like you over the past 30 days

Looking for cheap last minute flights or a weekend getaway? We've got you covered with weekend flight deals from Chicago to Puerto Rico. The chart below shows the best last minute deals and cheap flights this weekend we could find.

DestinationDepartingReturningPrice
Aguadilla 5/19/17 5/22/17 $491
Ponce 6/2/17 6/4/17 $1,626

Flight Schedule Summaries Last modified: Apr 28, 2017 8:52 -04:00Number of routes searched: 292Number of itineraries searched: 773,746

Chicago to San Juan, Puerto Rico
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American -
JetBlue -
United -
American BOS
American CLT
American DFW
American JFK
JetBlue BOS
JetBlue FLL
JetBlue JFK
Copa PTY
Major Airlines ATL
Major Airlines DTW
Major Airlines MSP
Major Airlines JFK
Frontier MCO
Spirit FLL
United BOS
United CLE
United EWR
United IAD

Cheap Domestic Flights from Chicago - CHI Last modified: Apr 28, 2017 8:52 -04:00Prices shown were found by travelers like you over the past 30 days

Cheap International Flights from Chicago - CHI Last modified: Apr 28, 2017 8:52 -04:00Prices shown were found by travelers like you over the past 30 days

Cheap Flights from Chicago to Puerto Rico - from $331 Round trip from CHI to PR