Find Cheap Flights from Chicago to Sint Maarten

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 Sint Maarten

(Round-trip)
Depart: Sat Sep 9 2017 Return: Sat Sep 16 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 33m
1 stop
SXM
ORD
10h 09m
1 stop
Depart: Sat Oct 21 2017 Return: Sat Oct 28 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
24h 52m
1 stop
SXM
ORD
21h 44m
1 stop
Depart: Sun May 28 2017 Return: Fri Jun 2 2017 Trip spans 6 days
American Airlines
American Airlines
ORD
SXM
17h 50m
1 stop
SXM
ORD
8h 44m
1 stop
Depart: Wed Jun 7 2017 Return: Mon Jun 12 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
17h 30m
1 stop
SXM
MDW
9h 01m
1 stop
Depart: Sat Apr 29 2017 Return: Tue May 2 2017 Trip spans 4 days
JetBlue
JetBlue
ORD
SXM
16h 11m
1 stop
SXM
ORD
29h 04m
1 stop
Depart: Sat Oct 14 2017 Return: Sat Oct 21 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 33m
1 stop
SXM
ORD
10h 09m
1 stop
Depart: Sat Aug 19 2017 Return: Sat Aug 26 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
20h 09m
1 stop
SXM
ORD
12h 51m
1 stop
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
8h 55m
1 stop
SXM
ORD
8h 44m
1 stop
Depart: Tue Jun 13 2017 Return: Tue Jun 20 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
6h 51m
1 stop
SXM
MDW
9h 01m
1 stop
Depart: Sat Sep 2 2017 Return: Sat Sep 9 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
10h 09m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
7h 10m
1 stop
SXM
ORD
8h 44m
1 stop
Depart: Tue Aug 1 2017 Return: Tue Aug 8 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
9h 03m
1 stop
Depart: Sat Oct 28 2017 Return: Sat Nov 4 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 33m
1 stop
SXM
ORD
10h 09m
1 stop
Depart: Wed Aug 30 2017 Return: Thu Aug 31 2017 Trip spans 2 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
9h 08m
1 stop
Depart: Thu Sep 7 2017 Return: Sun Sep 10 2017 Trip spans 4 days
Delta
Delta
MDW
SXM
6h 43m
1 stop
SXM
MDW
8h 53m
1 stop
Depart: Sat May 6 2017 Return: Sat May 13 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
17h 37m
2 stops
SXM
ORD
23h 51m
2 stops
Depart: Sat Jun 10 2017 Return: Tue Jun 20 2017 Trip spans 11 days
Delta
Delta
ORD
SXM
18h 20m
1 stop
SXM
ORD
9h 37m
1 stop
Depart: Tue Jul 25 2017 Return: Mon Jul 31 2017 Trip spans 7 days
Delta
Delta
ORD
SXM
6h 44m
1 stop
SXM
ORD
19h 45m
2 stops
Depart: Sat Jul 29 2017 Return: Sat Aug 5 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
ORD
SXM
7h 35m
1 stop
SXM
ORD
10h 06m
1 stop
Depart: Wed Jul 5 2017 Return: Mon Jul 10 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
9h 08m
1 stop
* 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.

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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,
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Airports
Origin

Chicago
only $478
only $520
Destination

Simpson Bay
$478