Find Deals on 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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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Chicago to San Juan

(Round-trip)
Depart: Mon May 1 2017 Return: Fri May 5 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 50m
1 stop
SJU
ORD
8h 42m
1 stop
Depart: Sat Apr 29 2017 Return: Thu May 4 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
6h 43m
nonstop
SJU
ORD
8h 56m
nonstop
Depart: Sat Apr 22 2017 Return: Fri Apr 28 2017 Trip spans 7 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
8h 45m
1 stop
Depart: Tue Apr 25 2017 Return: Thu Apr 27 2017 Trip spans 3 days
Delta
Delta
MDW
SJU
14h 03m
2 stops
SJU
MDW
9h 09m
1 stop
Depart: Tue Jul 4 2017 Return: Wed Jul 5 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SJU
4h 44m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
SJU
8h 30m
1 stop
SJU
ORD
6h 43m
1 stop
Depart: Tue Aug 15 2017 Return: Sat Aug 26 2017 Trip spans 12 days
Major Airline
Major Airline
ORD
SJU
27h 17m
nonstop
SJU
ORD
6h 43m
nonstop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
SJU
7h 17m
nonstop
SJU
ORD
6h 43m
nonstop
Depart: Fri Jun 16 2017 Return: Thu Jun 22 2017 Trip spans 7 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Tue May 2 2017 Return: Tue May 9 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
14h 09m
2 stops
SJU
MDW
7h 18m
1 stop
Depart: Thu Sep 7 2017 Return: Wed Sep 13 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
SJU
30h 04m
nonstop
SJU
ORD
30h 30m
nonstop
Depart: Tue Sep 26 2017 Return: Wed Oct 4 2017 Trip spans 9 days
Delta
Delta
MDW
SJU
13h 53m
2 stops
SJU
MDW
8h 03m
1 stop
Depart: Wed Jul 19 2017 Return: Wed Aug 2 2017 Trip spans 15 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Wed Sep 13 2017 Return: Wed Sep 20 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SJU
25h 10m
nonstop
SJU
ORD
10h 57m
nonstop
Depart: Thu May 11 2017 Return: Fri May 19 2017 Trip spans 9 days
Spirit Airlines
Spirit Airlines
ORD
SJU
18h 48m
1 stop
SJU
ORD
8h 42m
1 stop
Depart: Thu Jun 1 2017 Return: Fri Jun 9 2017 Trip spans 9 days
United
United
ORD
SJU
4h 45m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Wed Apr 26 2017 Return: Wed May 3 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
6h 25m
1 stop
SJU
MDW
8h 15m
1 stop
Depart: Thu May 11 2017 Return: Fri May 19 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
SJU
4h 34m
nonstop
SJU
ORD
5h 20m
nonstop
Depart: Thu Sep 14 2017 Return: Tue Sep 19 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
18h 04m
nonstop
SJU
ORD
25h 46m
nonstop
Depart: Mon May 1 2017 Return: Wed May 10 2017 Trip spans 10 days
Delta
Delta
MDW
SJU
6h 25m
1 stop
SJU
MDW
6h 40m
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 $330
only $389
Destination

San Juan
$330
Airlines Airline reviews

27 travelers who booked a flight from Chicago to San Juan rated their chosen airlines with an average of 6.6.

Overall
6.9
Boarding
6.3
Crew
7.0
Comfort
6.8
Food
6.5
Entertainment
6.6