Find Cheap Flights from Chicago to San Juan (CHI - PR1)

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: Wed Jan 17 2018 Return: Tue Jan 23 2018 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 48m
1 stop
SJU
ORD
32h 13m
1 stop
Depart: Sun Jan 21 2018 Return: Mon Jan 29 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
ORD
SJU
29h 11m
1 stop
SJU
ORD
31h 15m
1 stop
Depart: Tue Jan 23 2018 Return: Mon Jan 29 2018 Trip spans 7 days
Frontier
Frontier
ORD
SJU
14h 35m
1 stop
SJU
ORD
18h 25m
1 stop
Depart: Tue Dec 12 2017 Return: Thu Dec 14 2017 Trip spans 3 days
Multiple Airlines
Multiple Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
12h 29m
1 stop
Depart: Wed Nov 29 2017 Return: Wed Dec 6 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
32h 28m
1 stop
Depart: Thu Jan 18 2018 Return: Mon Jan 22 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
ORD
SJU
11h 29m
1 stop
SJU
ORD
19h 18m
1 stop
Depart: Wed Dec 6 2017 Return: Sat Dec 9 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Wed Nov 1 2017 Return: Thu Nov 30 2017 Trip spans 30 days
Spirit Airlines
Spirit Airlines
ORD
SJU
30h 56m
1 stop
SJU
ORD
19h 31m
1 stop
Depart: Wed Nov 1 2017 Return: Fri Dec 1 2017 Trip spans 31 days
Multiple Airlines
Multiple Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
14h 40m
1 stop
Depart: Sun Dec 10 2017 Return: Fri Dec 15 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
32h 28m
1 stop
Depart: Mon Dec 4 2017 Return: Tue Dec 5 2017 Trip spans 2 days
Multiple Airlines
Multiple Airlines
ORD
SJU
22h 34m
1 stop
SJU
ORD
15h 15m
1 stop
Depart: Wed Nov 29 2017 Return: Tue Dec 12 2017 Trip spans 14 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Tue Nov 7 2017 Return: Thu Nov 16 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
ORD
SJU
11h 44m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Tue Feb 6 2018 Return: Tue Feb 13 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 48m
1 stop
SJU
ORD
32h 13m
1 stop
Depart: Tue Nov 7 2017 Return: Mon Nov 13 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
ORD
SJU
11h 44m
1 stop
SJU
ORD
19h 31m
1 stop
Depart: Sat Nov 11 2017 Return: Thu Nov 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 28m
1 stop
Depart: Thu Dec 7 2017 Return: Tue Dec 12 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
ORD
SJU
14h 19m
1 stop
SJU
ORD
19h 41m
1 stop
Depart: Wed Nov 29 2017 Return: Mon Dec 11 2017 Trip spans 13 days
Spirit Airlines
Spirit Airlines
ORD
SJU
17h 52m
1 stop
SJU
ORD
21h 37m
2 stops
Depart: Mon Dec 4 2017 Return: Mon Dec 11 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
ORD
SJU
22h 34m
1 stop
SJU
ORD
21h 37m
2 stops
Depart: Thu Nov 30 2017 Return: Wed Dec 6 2017 Trip spans 7 days
Spirit Airlines
Spirit Airlines
ORD
SJU
6h 56m
1 stop
SJU
ORD
8h 28m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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We’re not the seller.
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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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

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
$211
Destination

San Juan
$211