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: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Frontier
Frontier
ORD
SJU
19h 11m
1 stop
SJU
ORD
11h 14m
1 stop
Depart: Mon Dec 4 2017 Return: Wed Dec 6 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
ORD
SJU
28h 37m
1 stop
SJU
ORD
8h 58m
1 stop
Depart: Sat Jan 13 2018 Return: Thu Jan 18 2018 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
14h 04m
1 stop
SJU
ORD
8h 20m
1 stop
Depart: Sun Oct 1 2017 Return: Tue Oct 3 2017 Trip spans 3 days
United
United
ORD
SJU
4h 40m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Tue Oct 31 2017 Return: Tue Nov 7 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SJU
4h 42m
nonstop
SJU
ORD
9h 44m
1 stop
Depart: Tue Sep 19 2017 Return: Wed Sep 27 2017 Trip spans 9 days
Delta
Delta
MDW
SJU
7h 35m
1 stop
SJU
MDW
10h 50m
2 stops
Depart: Wed Dec 6 2017 Return: Tue Dec 12 2017 Trip spans 7 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Wed Jan 24 2018 Return: Tue Feb 13 2018 Trip spans 21 days
Frontier
Frontier
ORD
SJU
19h 09m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
ORD
SJU
12h 32m
1 stop
SJU
ORD
18h 00m
1 stop
Depart: Wed Jan 24 2018 Return: Mon Feb 12 2018 Trip spans 20 days
Frontier
Frontier
ORD
SJU
19h 09m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Wed Feb 7 2018 Return: Mon Feb 12 2018 Trip spans 6 days
Frontier
Frontier
ORD
SJU
19h 09m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Tue Oct 24 2017 Return: Mon Oct 30 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
ORD
SJU
14h 59m
1 stop
SJU
ORD
26h 49m
1 stop
Depart: Mon Sep 25 2017 Return: Fri Sep 29 2017 Trip spans 5 days
United
United
ORD
SJU
4h 40m
nonstop
SJU
ORD
5h 05m
nonstop
Depart: Thu Sep 7 2017 Return: Mon Sep 11 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
SJU
17h 39m
1 stop
SJU
ORD
6h 43m
1 stop
Depart: Sat Jan 13 2018 Return: Fri Jan 19 2018 Trip spans 7 days
Delta
Delta
MDW
SJU
18h 33m
2 stops
SJU
MDW
16h 10m
2 stops
Depart: Thu Nov 30 2017 Return: Mon Dec 11 2017 Trip spans 12 days
Frontier
Frontier
ORD
SJU
19h 07m
1 stop
SJU
ORD
11h 36m
1 stop
Depart: Wed Nov 1 2017 Return: Tue Nov 7 2017 Trip spans 7 days
United
United
ORD
SJU
4h 35m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Wed Jan 17 2018 Return: Tue Jan 23 2018 Trip spans 7 days
Delta
Delta
MDW
SJU
12h 06m
2 stops
SJU
MDW
7h 03m
1 stop
Depart: Sun Sep 17 2017 Return: Fri Sep 22 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
ORD
SJU
17h 39m
1 stop
SJU
ORD
18h 26m
1 stop
Depart: Tue Jan 23 2018 Return: Mon Jan 29 2018 Trip spans 7 days
Frontier
Frontier
ORD
SJU
14h 30m
1 stop
SJU
ORD
18h 25m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Why aren’t prices accurate 100% of the time?
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 $229
only $389
Destination

San Juan
$229
Airlines Airline reviews

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

Overall
7.4
Boarding
6.8
Crew
7.4
Comfort
6.8
Food
6.6
Entertainment
7.1