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: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
25h 20m
1 stop
SJU
ORD
22h 47m
1 stop
Depart: Wed Aug 9 2017 Return: Tue Aug 29 2017 Trip spans 21 days
Frontier
Frontier
ORD
SJU
17h 16m
1 stop
SJU
ORD
18h 02m
1 stop
Depart: Mon Sep 25 2017 Return: Sat Sep 30 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 53m
1 stop
SJU
ORD
8h 32m
1 stop
Depart: Tue Oct 17 2017 Return: Wed Nov 8 2017 Trip spans 23 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Wed Sep 27 2017 Return: Tue Oct 3 2017 Trip spans 7 days
Delta
Delta
MDW
SJU
13h 53m
2 stops
SJU
MDW
10h 32m
2 stops
Depart: Fri Nov 17 2017 Return: Thu Nov 23 2017 Trip spans 7 days
United
United
ORD
SJU
16h 05m
1 stop
SJU
ORD
5h 10m
nonstop
Depart: Fri Aug 18 2017 Return: Tue Aug 22 2017 Trip spans 5 days
Frontier
Frontier
ORD
SJU
17h 26m
1 stop
SJU
ORD
18h 02m
1 stop
Depart: Sat Aug 19 2017 Return: Sun Aug 27 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
14h 04m
nonstop
SJU
ORD
12h 53m
nonstop
Depart: Wed Sep 27 2017 Return: Sun Oct 1 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SJU
13h 20m
nonstop
SJU
ORD
6h 49m
nonstop
Depart: Thu Oct 5 2017 Return: Thu Oct 12 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
8h 35m
nonstop
SJU
ORD
11h 28m
nonstop
Depart: Tue Sep 12 2017 Return: Thu Sep 28 2017 Trip spans 17 days
Delta
Delta
MDW
SJU
13h 53m
2 stops
SJU
MDW
9h 53m
1 stop
Depart: Thu Aug 10 2017 Return: Sat Aug 19 2017 Trip spans 10 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 16m
1 stop
Depart: Thu Jul 27 2017 Return: Sun Jul 30 2017 Trip spans 4 days
Frontier
Frontier
ORD
SJU
17h 33m
1 stop
SJU
ORD
17h 32m
1 stop
Depart: Sun Oct 1 2017 Return: Wed Oct 4 2017 Trip spans 4 days
Delta
Delta
MDW
SJU
7h 52m
1 stop
SJU
MDW
10h 37m
2 stops
Depart: Fri Jul 7 2017 Return: Fri Jul 14 2017 Trip spans 8 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
19h 21m
1 stop
Depart: Fri Aug 18 2017 Return: Sat Aug 26 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
28h 15m
nonstop
SJU
ORD
12h 42m
nonstop
Depart: Wed Nov 22 2017 Return: Wed Nov 29 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Sat Oct 21 2017 Return: Sat Oct 28 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
14h 54m
2 stops
SJU
MDW
9h 51m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 14 2017 Trip spans 14 days
Major Airline
Major Airline
ORD
SJU
8h 18m
nonstop
SJU
ORD
12h 45m
nonstop
Depart: Sat Nov 11 2017 Return: Wed Nov 15 2017 Trip spans 5 days
Delta
Delta
MDW
SJU
11h 14m
2 stops
SJU
MDW
8h 03m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
only $294
only $379
Destination

San Juan
$294
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
7.6
Boarding
7.0
Crew
7.6
Comfort
7.0
Food
6.6
Entertainment
7.2