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
Students
under 26
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: Wed Jan 25 2017 Return: Wed Feb 1 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
13h 39m
1 stop
SJU
ORD
12h 07m
1 stop
Depart: Thu Feb 23 2017 Return: Sat Mar 4 2017 Trip spans 10 days
Major Airline
Major Airline
ORD
SJU
15h 51m
1 stop
SJU
ORD
14h 10m
1 stop
Depart: Mon Mar 6 2017 Return: Tue Mar 14 2017 Trip spans 8 days
JetBlue
JetBlue
ORD
SJU
12h 10m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Mon Jan 23 2017 Return: Thu Jan 26 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
SJU
4h 30m
nonstop
SJU
ORD
5h 27m
nonstop
Depart: Thu May 4 2017 Return: Wed May 10 2017 Trip spans 7 days
United
United
ORD
SJU
4h 50m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Wed Jan 18 2017 Return: Sat Jan 28 2017 Trip spans 11 days
Delta
Delta
MDW
SJU
13h 06m
2 stops
SJU
MDW
16h 07m
2 stops
Depart: Sat Jan 28 2017 Return: Wed Feb 1 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
12h 29m
1 stop
SJU
ORD
12h 07m
1 stop
Depart: Tue Mar 7 2017 Return: Mon Mar 13 2017 Trip spans 6 days
Major Airline
Major Airline
ORD
SJU
7h 15m
nonstop
SJU
ORD
8h 13m
nonstop
Depart: Tue Apr 4 2017 Return: Tue Apr 18 2017 Trip spans 15 days
JetBlue
JetBlue
ORD
SJU
12h 10m
1 stop
SJU
ORD
27h 11m
1 stop
Depart: Mon Mar 27 2017 Return: Tue Apr 4 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
28h 28m
nonstop
SJU
ORD
27h 11m
nonstop
Depart: Fri Jan 27 2017 Return: Tue Jan 31 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 53m
1 stop
SJU
ORD
12h 07m
1 stop
Depart: Mon Jun 19 2017 Return: Thu Jun 29 2017 Trip spans 11 days
American Airlines
American Airlines
ORD
SJU
4h 55m
nonstop
SJU
ORD
5h 02m
nonstop
Depart: Wed Feb 22 2017 Return: Thu Mar 2 2017 Trip spans 9 days
JetBlue
JetBlue
ORD
SJU
8h 33m
1 stop
SJU
ORD
9h 49m
1 stop
Depart: Thu Feb 23 2017 Return: Fri Mar 3 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SJU
7h 55m
nonstop
SJU
ORD
8h 44m
nonstop
Depart: Sat Dec 31 2016 Return: Thu Jan 12 2017 Trip spans 13 days
United
United
ORD
SJU
4h 35m
nonstop
SJU
ORD
8h 07m
1 stop
Depart: Sun May 21 2017 Return: Sat Jun 10 2017 Trip spans 21 days
American Airlines
American Airlines
ORD
SJU
8h 20m
1 stop
SJU
ORD
6h 48m
1 stop
Depart: Tue Mar 28 2017 Return: Tue Apr 4 2017 Trip spans 8 days
Delta
Delta
MDW
SJU
16h 14m
2 stops
SJU
MDW
14h 02m
2 stops
Depart: Mon Apr 10 2017 Return: Wed Apr 19 2017 Trip spans 10 days
United
United
ORD
SJU
4h 50m
nonstop
SJU
ORD
5h 10m
nonstop
Depart: Mon Jun 5 2017 Return: Tue Jun 13 2017 Trip spans 9 days
American Airlines
American Airlines
ORD
SJU
8h 23m
1 stop
SJU
ORD
8h 52m
1 stop
Depart: Tue Feb 7 2017 Return: Wed Feb 15 2017 Trip spans 9 days
Delta
Delta
MDW
SJU
15h 20m
2 stops
SJU
MDW
8h 01m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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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 $205
only $343
Destination

San Juan
$205
Airlines Airline reviews

22 travelers who booked a flight from Chicago to San Juan rated their chosen airlines with an average of 6.4.

Overall
6.7
Boarding
6.1
Crew
6.7
Comfort
6.4
Food
6.2
Entertainment
6.2