Find Cheap Flights from Caribbean to Chicago O'Hare International

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 Caribbean to Chicago O'Hare International

(Round-trip)
Depart: Tue Aug 22 2017 Return: Tue Aug 29 2017 Trip spans 8 days
Frontier
Frontier
SJU
ORD
17h 37m
1 stop
ORD
SJU
17h 40m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 26 2017 Trip spans 16 days
Multiple Airlines
Multiple Airlines
SJU
ORD
18h 00m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Fri Aug 11 2017 Return: Sat Aug 26 2017 Trip spans 16 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 54m
1 stop
ORD
BQN
8h 14m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
JetBlue
JetBlue
NAS
ORD
8h 54m
1 stop
ORD
NAS
9h 48m
1 stop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
United
United
MBJ
ORD
4h 25m
nonstop
ORD
MBJ
7h 10m
1 stop
Depart: Wed Dec 20 2017 Return: Wed Jan 3 2018 Trip spans 15 days
Delta
Delta
MBJ
ORD
18h 41m
2 stops
ORD
MBJ
8h 40m
1 stop
Depart: Fri Aug 11 2017 Return: Sun Aug 13 2017 Trip spans 3 days
American Airlines
American Airlines
SJU
ORD
8h 10m
1 stop
ORD
SJU
9h 11m
1 stop
Depart: Fri Nov 17 2017 Return: Fri Dec 1 2017 Trip spans 15 days
Copa Airlines
Copa Airlines
STI
ORD
9h 18m
1 stop
ORD
STI
23h 36m
1 stop
Depart: Mon Sep 11 2017 Return: Tue Sep 26 2017 Trip spans 16 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Mon Oct 2 2017 Return: Tue Oct 10 2017 Trip spans 9 days
Multiple Airlines
Multiple Airlines
SJU
ORD
18h 00m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Thu Sep 14 2017 Return: Mon Sep 18 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
9h 10m
1 stop
Depart: Tue Sep 12 2017 Return: Mon Sep 18 2017 Trip spans 7 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Wed Oct 11 2017 Return: Mon Oct 16 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 43m
1 stop
ORD
SJU
8h 25m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 21 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
SJU
ORD
17h 37m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Frontier
Frontier
SJU
ORD
18h 00m
1 stop
ORD
SJU
17h 39m
1 stop
Depart: Sun Dec 24 2017 Return: Sat Jan 6 2018 Trip spans 14 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Fri Nov 3 2017 Return: Sun Nov 5 2017 Trip spans 3 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
6h 54m
1 stop
Depart: Wed Dec 6 2017 Return: Mon Dec 11 2017 Trip spans 6 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 28m
1 stop
ORD
SJU
12h 20m
1 stop
Depart: Thu Jan 18 2018 Return: Sun Jan 21 2018 Trip spans 4 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Tue Nov 7 2017 Return: Sun Nov 12 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 42m
1 stop
ORD
SJU
6h 55m
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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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

Aguadilla
$301
Nassau
$322
San Juan
$279
Montego Bay
$343
Santiago de los Caballeros
$509
Destination

Chicago
$279
Airlines Airline reviews

13 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.9.

Overall
8.6
Boarding
8.1
Crew
8.5
Comfort
8.1
Food
6.9
Entertainment
7.4