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: Mon Oct 16 2017 Return: Tue Oct 24 2017 Trip spans 9 days
Frontier
Frontier
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Wed Sep 27 2017 Return: Sat Sep 30 2017 Trip spans 4 days
JetBlue
JetBlue
SJU
ORD
6h 49m
1 stop
ORD
SJU
6h 41m
1 stop
Depart: Wed Oct 4 2017 Return: Wed Oct 11 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
18h 48m
1 stop
Depart: Tue Oct 10 2017 Return: Tue Oct 17 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Sat Sep 23 2017 Return: Sat Oct 7 2017 Trip spans 15 days
American Airlines
American Airlines
SJU
ORD
7h 23m
1 stop
ORD
SJU
4h 42m
nonstop
Depart: Mon Oct 23 2017 Return: Sun Oct 29 2017 Trip spans 7 days
United
United
SJU
ORD
5h 05m
nonstop
ORD
SJU
4h 35m
nonstop
Depart: Thu Oct 5 2017 Return: Fri Oct 13 2017 Trip spans 9 days
Major Airline
Major Airline
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Thu Sep 28 2017 Return: Thu Oct 5 2017 Trip spans 8 days
Delta
Delta
SJU
ORD
11h 35m
2 stops
ORD
SJU
6h 24m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Frontier
Frontier
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Wed Oct 11 2017 Return: Wed Oct 18 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
12h 32m
1 stop
Depart: Sat Oct 7 2017 Return: Sat Oct 14 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 35m
1 stop
ORD
SJU
18h 48m
1 stop
Depart: Thu Nov 16 2017 Return: Mon Dec 4 2017 Trip spans 19 days
JetBlue
JetBlue
BGI
ORD
17h 33m
1 stop
ORD
BGI
9h 40m
1 stop
Depart: Tue Dec 5 2017 Return: Sun Dec 10 2017 Trip spans 6 days
Frontier
Frontier
SJU
ORD
15h 00m
1 stop
ORD
SJU
14h 30m
1 stop
Depart: Mon Sep 25 2017 Return: Fri Sep 29 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
SJU
ORD
23h 30m
1 stop
ORD
SJU
6h 41m
1 stop
Depart: Mon Sep 25 2017 Return: Sat Sep 30 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
SJU
ORD
23h 30m
1 stop
ORD
SJU
18h 48m
1 stop
Depart: Tue Oct 17 2017 Return: Tue Oct 24 2017 Trip spans 8 days
Multiple Airlines
Multiple Airlines
SJU
ORD
14h 03m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Tue Nov 28 2017 Return: Wed Nov 29 2017 Trip spans 2 days
JetBlue
JetBlue
NAS
ORD
5h 17m
1 stop
ORD
NAS
7h 11m
1 stop
Depart: Wed Oct 18 2017 Return: Thu Oct 26 2017 Trip spans 9 days
Major Airline
Major Airline
SJU
ORD
18h 25m
1 stop
ORD
SJU
14h 59m
1 stop
Depart: Sat Nov 4 2017 Return: Sat Nov 11 2017 Trip spans 8 days
United
United
BQN
ORD
8h 31m
1 stop
ORD
BQN
13h 20m
1 stop
Depart: Mon Oct 9 2017 Return: Mon Oct 16 2017 Trip spans 8 days
American Airlines
American Airlines
SJU
ORD
5h 17m
nonstop
ORD
SJU
4h 42m
nonstop
* 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
$373
Bridgetown
$322
Nassau
$335
San Juan
$284
Destination

Chicago
$284
Airlines Airline reviews

58 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.8.

Overall
8.2
Boarding
8.1
Crew
8.2
Comfort
8.0
Food
7.2
Entertainment
7.2