Find Deals on Flights from Chicago to Simpson Bay Princess Juliana (CHI - SXM)

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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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

Book cheap flights from Chicago to Simpson Bay Princess Juliana

(Round-trip)
Depart: Sat Jan 7 2017 Return: Sat Jan 14 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
9h 06m
1 stop
Depart: Fri May 5 2017 Return: Sat May 13 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SXM
7h 30m
1 stop
SXM
ORD
8h 00m
1 stop
Depart: Tue Jan 24 2017 Return: Sun Jan 29 2017 Trip spans 6 days
United
United
ORD
SXM
18h 40m
2 stops
SXM
ORD
20h 26m
2 stops
Depart: Sun Mar 5 2017 Return: Mon Mar 6 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SXM
17h 40m
1 stop
SXM
ORD
8h 45m
1 stop
Depart: Mon Jan 9 2017 Return: Sun Jan 15 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
6h 50m
1 stop
SXM
MDW
8h 43m
1 stop
Depart: Sat Feb 4 2017 Return: Sat Feb 11 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
26h 25m
nonstop
SXM
ORD
19h 10m
nonstop
Depart: Sat Apr 29 2017 Return: Mon May 8 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
SXM
17h 40m
1 stop
SXM
ORD
8h 27m
1 stop
Depart: Wed Jan 25 2017 Return: Thu Feb 2 2017 Trip spans 9 days
Delta
Delta
MDW
SXM
6h 50m
1 stop
SXM
MDW
8h 46m
1 stop
Depart: Sat Apr 29 2017 Return: Fri May 5 2017 Trip spans 7 days
Major Airline
Major Airline
ORD
SXM
16h 11m
1 stop
SXM
ORD
8h 20m
1 stop
Depart: Thu Jun 8 2017 Return: Thu Jun 15 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
6h 48m
1 stop
SXM
ORD
17h 11m
1 stop
Depart: Wed Feb 1 2017 Return: Sun Feb 5 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
6h 50m
1 stop
SXM
MDW
8h 43m
1 stop
Depart: Sun Jan 29 2017 Return: Sun Feb 5 2017 Trip spans 8 days
United
United
ORD
SXM
5h 10m
nonstop
SXM
ORD
5h 55m
nonstop
Depart: Thu Mar 16 2017 Return: Tue Mar 21 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 22m
1 stop
Depart: Sun Mar 26 2017 Return: Sun Apr 2 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
24h 01m
1 stop
SXM
ORD
16h 35m
1 stop
Depart: Sat Mar 25 2017 Return: Thu Mar 30 2017 Trip spans 6 days
Delta
Delta
ORD
SXM
17h 59m
1 stop
SXM
ORD
9h 30m
1 stop
Depart: Fri Feb 10 2017 Return: Sat Feb 18 2017 Trip spans 9 days
Major Airline
Major Airline
ORD
SXM
8h 05m
1 stop
SXM
ORD
16h 40m
1 stop
Depart: Wed Apr 12 2017 Return: Tue Apr 18 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 24m
1 stop
Depart: Sat Apr 29 2017 Return: Sat May 6 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
25h 01m
2 stops
SXM
ORD
21h 14m
2 stops
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
20h 25m
2 stops
SXM
MDW
7h 52m
1 stop
Depart: Sat Jan 14 2017 Return: Fri Jan 20 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
23h 05m
1 stop
SXM
MDW
8h 46m
1 stop
Select an airline:  United
Direct flights CHI to SXM on United
Flight # Depart ORD Arrive SXM Sun Mon Tue Wed Thu Fri Sat Valid Between
1671 8:15 am 3:25 pm Dec 3 - Dec 17
1671 8:15 am 3:25 pm Dec 18 - Feb 18
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

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.

We compile tonnes of data for you
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.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Chicago
only $468
only $514
Destination

Simpson Bay
$468
Airlines Airline reviews

3 travelers who booked a flight from Chicago to Simpson Bay rated their chosen airlines with an average of 4.8.

Overall
5.3
Boarding
5.3
Crew
6.7
Comfort
4.7
Food
3.3
Entertainment
3.3