Find Cheap Flights from Chicago to Puerto Rico

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Book cheap flights from Chicago to Puerto Rico (round-trip)

Airports
Origin
Chicago
$189
only
$189
$362
only
$362
Destination
Aguadilla
$210
only
$210
San Juan
$189
only
$189
Ponce
$363
only
$363
Tue, Apr 10
ORD
SJU
7h 31m
Mon, Apr 16
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Apr 4
ORD
BQN
6h 24m
Tue, Apr 10
BQN
ORD
9h 07m
Trip: 7 days
Overall null null
Based on null reviews
Tue, Mar 6
ORD
BQN
18h 11m
Mon, Mar 12
BQN
ORD
9h 07m
Trip: 6 days
Overall null null
Based on null reviews
Thu, Jun 7
ORD
SJU
4h 50m
Thu, Jun 14
SJU
ORD
5h 10m
Trip: 8 days
Overall null null
Based on null reviews
Fri, Mar 16
MDW
SJU
6h 25m
Tue, Mar 20
SJU
MDW
7h 40m
Trip: 5 days
Overall null null
Based on null reviews
Sat, Jun 9
ORD
PSE
7h 51m
Wed, Jul 4
PSE
ORD
8h 53m
Trip: 26 days
Overall null null
Based on null reviews
Sat, Mar 3
ORD
SJU
4h 29m
Fri, Mar 9
SJU
ORD
5h 35m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Apr 11
ORD
SJU
7h 31m
Tue, Apr 17
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Apr 11
ORD
SJU
7h 31m
Tue, Apr 17
SJU
ORD
8h 38m
Trip: 7 days
Overall null null
Based on null reviews
Mon, Feb 26
ORD
SJU
17h 51m
Mon, Mar 5
SJU
ORD
19h 29m
Trip: 8 days
Overall null null
Based on null reviews
Tue, May 1
ORD
SJU
7h 32m
Mon, May 7
SJU
ORD
8h 26m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Jun 6
ORD
SJU
7h 32m
Tue, Jun 12
SJU
ORD
20h 45m
Trip: 7 days
Overall null null
Based on null reviews
Tue, May 1
ORD
SJU
7h 32m
Mon, May 7
SJU
ORD
8h 26m
Trip: 7 days
Overall null null
Based on null reviews
Tue, May 8
ORD
BQN
8h 26m
Tue, May 15
BQN
ORD
8h 47m
Trip: 8 days
Overall null null
Based on null reviews
Tue, Jun 5
ORD
SJU
7h 32m
Mon, Jun 11
SJU
ORD
8h 32m
Trip: 7 days
Overall null null
Based on null reviews
Tue, Jul 17
ORD
SJU
6h 56m
Mon, Jul 23
SJU
ORD
8h 31m
Trip: 7 days
Overall null null
Based on null reviews
Fri, May 11
ORD
BQN
6h 12m
Thu, May 17
BQN
ORD
8h 47m
Trip: 7 days
Overall null null
Based on null reviews
Tue, Jun 26
ORD
SJU
7h 32m
Mon, Jul 2
SJU
ORD
8h 31m
Trip: 7 days
Overall null null
Based on null reviews
Wed, Jul 4
ORD
SJU
7h 39m
Mon, Jul 9
SJU
ORD
8h 31m
Trip: 6 days
Overall null null
Based on null reviews
Tue, May 1
ORD
BQN
8h 26m
Tue, May 8
BQN
ORD
27h 51m
Trip: 8 days
Overall null null
Based on null reviews

Chicago to Puerto Rico Flight Information

Flights Arrive in Puerto Rico
Flights Depart from Chicago
Flight Price $189
Airlines Frontier, Spirit Airlines, United, Delta, JetBlue, American Airlines
*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

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