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

Book cheap flights from Caribbean to Chicago O'Hare International

(Round-trip)
Depart: Tue Sep 5 2017 Return: Wed Sep 6 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SJU
ORD
8h 16m
1 stop
ORD
SJU
6h 56m
1 stop
Depart: Thu Oct 19 2017 Return: Tue Oct 24 2017 Trip spans 6 days
American Airlines
American Airlines
STT
ORD
8h 07m
1 stop
ORD
STT
6h 45m
1 stop
Depart: Wed Aug 9 2017 Return: Tue Aug 22 2017 Trip spans 14 days
Major Airline
Major Airline
SJU
ORD
6h 43m
nonstop
ORD
SJU
9h 07m
nonstop
Depart: Sun Oct 8 2017 Return: Tue Oct 24 2017 Trip spans 17 days
JetBlue
JetBlue
BQN
ORD
21h 59m
1 stop
ORD
BQN
15h 21m
1 stop
Depart: Sat Jul 15 2017 Return: Tue Jul 18 2017 Trip spans 4 days
United
United
NAS
ORD
22h 08m
2 stops
ORD
NAS
6h 43m
1 stop
Depart: Wed Sep 13 2017 Return: Mon Sep 18 2017 Trip spans 6 days
Delta
Delta
MBJ
ORD
8h 54m
1 stop
ORD
MBJ
16h 30m
1 stop
Depart: Wed Jun 7 2017 Return: Tue Jun 13 2017 Trip spans 7 days
Air Canada
Air Canada
KIN
ORD
16h 38m
1 stop
ORD
KIN
17h 52m
1 stop
Depart: Thu Jun 15 2017 Return: Mon Jun 19 2017 Trip spans 5 days
Copa Airlines
Copa Airlines
SDQ
ORD
19h 55m
1 stop
ORD
SDQ
27h 58m
1 stop
Depart: Mon Oct 2 2017 Return: Tue Oct 3 2017 Trip spans 2 days
Spirit Airlines
Spirit Airlines
SJU
ORD
6h 44m
1 stop
ORD
SJU
6h 53m
1 stop
Depart: Wed Jun 14 2017 Return: Mon Jun 26 2017 Trip spans 13 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 37m
1 stop
ORD
BQN
8h 14m
1 stop
Depart: Wed Aug 16 2017 Return: Tue Aug 22 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
6h 43m
nonstop
ORD
SJU
11h 18m
nonstop
Depart: Wed Sep 6 2017 Return: Sat Sep 30 2017 Trip spans 25 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 50m
1 stop
ORD
BQN
7h 36m
1 stop
Depart: Sat Jun 17 2017 Return: Fri Jun 23 2017 Trip spans 7 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Wed Aug 2 2017 Return: Wed Aug 9 2017 Trip spans 8 days
American Airlines
American Airlines
MBJ
ORD
19h 17m
1 stop
ORD
MBJ
13h 15m
1 stop
Depart: Fri Oct 6 2017 Return: Sun Oct 8 2017 Trip spans 3 days
JetBlue
JetBlue
NAS
ORD
8h 54m
1 stop
ORD
NAS
6h 08m
1 stop
Depart: Sun Jun 11 2017 Return: Sat Jun 17 2017 Trip spans 7 days
Major Airline
Major Airline
SJU
ORD
8h 28m
nonstop
ORD
SJU
6h 56m
nonstop
Depart: Sun Nov 5 2017 Return: Wed Nov 8 2017 Trip spans 4 days
Spirit Airlines
Spirit Airlines
BQN
ORD
7h 25m
1 stop
ORD
BQN
8h 01m
1 stop
Depart: Sat Jul 29 2017 Return: Fri Aug 4 2017 Trip spans 7 days
United
United
SJU
ORD
5h 10m
nonstop
ORD
SJU
4h 45m
nonstop
Depart: Wed Sep 13 2017 Return: Mon Sep 18 2017 Trip spans 6 days
Delta
Delta
PUJ
ORD
18h 56m
2 stops
ORD
PUJ
17h 34m
1 stop
Depart: Mon Jul 17 2017 Return: Wed Aug 2 2017 Trip spans 17 days
Spirit Airlines
Spirit Airlines
BQN
ORD
8h 54m
1 stop
ORD
BQN
17h 24m
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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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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please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Aguadilla
$331
Santo Domingo
$592
Nassau
$392
San Juan
$300
Saint Thomas Island
$345
Montego Bay
$408
Kingston
$541
Punta Cana
$451
Destination

Chicago
$300
Airlines Airline reviews

4 travelers who booked a flight from San Juan to Chicago rated their chosen airlines with an average of 7.0.

Overall
7.5
Boarding
6.0
Crew
7.0
Comfort
7.0
Food
7.0
Entertainment
7.5