Find Cheap Flights from Chicago to San Juan

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Book cheap flights from Chicago to San Juan

(Round-trip)
Depart: Fri Sep 8 2017 Return: Sun Sep 10 2017 Trip spans 3 days
Major Airline
Major Airline
ORD
SJU
11h 21m
nonstop
SJU
ORD
11h 04m
nonstop
Depart: Tue Aug 15 2017 Return: Wed Aug 23 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 16m
1 stop
Depart: Tue Sep 5 2017 Return: Wed Sep 20 2017 Trip spans 16 days
Delta
Delta
MDW
SJU
7h 52m
1 stop
SJU
MDW
8h 03m
1 stop
Depart: Mon Aug 28 2017 Return: Fri Sep 1 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Tue Jun 20 2017 Return: Sun Jun 25 2017 Trip spans 6 days
JetBlue
JetBlue
ORD
SJU
11h 23m
1 stop
SJU
ORD
30h 51m
1 stop
Depart: Sun Jul 9 2017 Return: Mon Jul 31 2017 Trip spans 23 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Wed Aug 16 2017 Return: Sun Aug 20 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJU
6h 37m
nonstop
SJU
ORD
12h 49m
nonstop
Depart: Sun Sep 10 2017 Return: Thu Sep 14 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 51m
1 stop
SJU
ORD
8h 36m
1 stop
Depart: Wed Sep 6 2017 Return: Wed Sep 13 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
7h 52m
1 stop
SJU
MDW
8h 03m
1 stop
Depart: Thu Aug 24 2017 Return: Mon Aug 28 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJU
24h 26m
nonstop
SJU
ORD
18h 32m
nonstop
Depart: Fri Oct 27 2017 Return: Fri Nov 3 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 51m
1 stop
SJU
ORD
8h 36m
1 stop
Depart: Fri Jul 21 2017 Return: Fri Jul 28 2017 Trip spans 8 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
10h 33m
1 stop
Depart: Mon May 29 2017 Return: Wed Jun 7 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
SJU
9h 06m
1 stop
SJU
ORD
8h 21m
1 stop
Depart: Mon Oct 2 2017 Return: Wed Oct 11 2017 Trip spans 10 days
Delta
Delta
MDW
SJU
6h 54m
1 stop
SJU
MDW
8h 03m
1 stop
Depart: Fri Sep 22 2017 Return: Sat Sep 30 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
15h 37m
nonstop
SJU
ORD
16h 32m
nonstop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
6h 54m
1 stop
SJU
MDW
7h 29m
1 stop
Depart: Thu Jun 1 2017 Return: Tue Jun 6 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
SJU
7h 54m
1 stop
SJU
ORD
8h 14m
1 stop
Depart: Tue Oct 3 2017 Return: Wed Oct 11 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
6h 51m
1 stop
SJU
ORD
8h 36m
1 stop
Depart: Fri Jun 16 2017 Return: Sat Jun 24 2017 Trip spans 9 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Sat Oct 28 2017 Return: Thu Nov 2 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
6h 50m
nonstop
SJU
ORD
18h 52m
nonstop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

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Airports
Origin

Chicago
only $330
only $362
Destination

San Juan
$330
Airlines Airline reviews

33 travelers who booked a flight from Chicago to San Juan rated their chosen airlines with an average of 7.0.

Overall
7.3
Boarding
6.8
Crew
7.3
Comfort
6.8
Food
6.6
Entertainment
7.1