Find Cheap Flights to Simpson Bay Princess Juliana

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 Simpson Bay Princess Juliana

(Round-trip)
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
10h 06m
1 stop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
American Airlines
American Airlines
ORD
SXM
6h 59m
1 stop
SXM
ORD
7h 39m
1 stop
Depart: Thu Sep 14 2017 Return: Sun Sep 17 2017 Trip spans 4 days
Delta
Delta
MDW
SXM
6h 45m
1 stop
SXM
MDW
8h 55m
1 stop
Depart: Sat Nov 4 2017 Return: Sun Nov 12 2017 Trip spans 9 days
Copa Airlines
Copa Airlines
ORD
SXM
20h 03m
1 stop
SXM
ORD
12h 57m
1 stop
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
United
United
ORD
SXM
5h 10m
nonstop
SXM
ORD
5h 55m
nonstop
Depart: Sat Nov 11 2017 Return: Sat Nov 18 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
10h 06m
1 stop
Depart: Tue Jan 2 2018 Return: Tue Jan 9 2018 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
17h 40m
1 stop
SXM
ORD
8h 48m
1 stop
Depart: Sat Oct 14 2017 Return: Sat Oct 21 2017 Trip spans 8 days
Delta
Delta
ORD
SXM
17h 03m
1 stop
SXM
ORD
9h 43m
1 stop
Depart: Sat Dec 2 2017 Return: Sat Dec 9 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
10h 06m
1 stop
Depart: Sat Sep 23 2017 Return: Sat Sep 30 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
14h 10m
1 stop
SXM
ORD
18h 00m
1 stop
Depart: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
Delta
Delta
MDW
SXM
7h 28m
1 stop
SXM
MDW
9h 03m
1 stop
Depart: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 32m
1 stop
SXM
ORD
10h 14m
1 stop
Depart: Thu Nov 30 2017 Return: Mon Dec 4 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
6h 53m
1 stop
SXM
MDW
19h 41m
1 stop
Depart: Sat Feb 10 2018 Return: Sat Feb 24 2018 Trip spans 15 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 32m
1 stop
SXM
ORD
10h 16m
1 stop
Depart: Tue Jan 2 2018 Return: Tue Jan 9 2018 Trip spans 8 days
Delta
Delta
MDW
SXM
17h 12m
1 stop
SXM
MDW
19h 40m
1 stop
Depart: Sat Jan 27 2018 Return: Sat Feb 3 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 32m
1 stop
SXM
ORD
10h 14m
1 stop
Depart: Wed Nov 15 2017 Return: Sun Nov 19 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
8h 41m
1 stop
SXM
ORD
10h 44m
1 stop
Depart: Sat Oct 14 2017 Return: Sat Oct 21 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
18h 33m
2 stops
SXM
MDW
8h 39m
1 stop
Depart: Sat Oct 28 2017 Return: Fri Nov 3 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
18h 35m
2 stops
SXM
MDW
19h 10m
2 stops
Depart: Sat Dec 9 2017 Return: Sun Dec 17 2017 Trip spans 9 days
Delta
Delta
MDW
SXM
18h 45m
2 stops
SXM
MDW
18h 55m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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Airports
Origin

Chicago
only $460
only $526
Destination

Simpson Bay
$460
Airlines Airline reviews

4 travelers who booked a flight from Chicago to Simpson Bay rated their chosen airlines with an average of 5.6.

Overall
6.0
Boarding
6.0
Crew
7.0
Comfort
5.5
Food
4.5
Entertainment
4.5