Find Deals on 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: Sun Aug 13 2017 Return: Mon Aug 14 2017 Trip spans 2 days
American Airlines
American Airlines
ORD
SXM
17h 40m
1 stop
SXM
ORD
17h 11m
1 stop
Depart: Mon Mar 27 2017 Return: Mon Apr 3 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
25h 49m
1 stop
SXM
ORD
12h 51m
1 stop
Depart: Sun May 14 2017 Return: Fri May 19 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 24m
1 stop
Depart: Sat Apr 1 2017 Return: Tue Apr 4 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
SXM
29h 46m
2 stops
SXM
ORD
9h 53m
2 stops
Depart: Thu Apr 20 2017 Return: Thu Apr 27 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
6h 49m
1 stop
SXM
ORD
8h 51m
1 stop
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
17h 29m
1 stop
SXM
MDW
8h 24m
1 stop
Depart: Wed May 10 2017 Return: Tue May 16 2017 Trip spans 7 days
American Airlines
American Airlines
ORD
SXM
6h 55m
1 stop
SXM
ORD
10h 36m
1 stop
Depart: Thu Jun 8 2017 Return: Fri Jun 16 2017 Trip spans 9 days
Delta
Delta
MDW
SXM
17h 29m
1 stop
SXM
MDW
9h 08m
1 stop
Depart: Sun Jun 4 2017 Return: Thu Jun 8 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
6h 45m
1 stop
SXM
ORD
10h 22m
1 stop
Depart: Tue Jul 18 2017 Return: Tue Jul 25 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
9h 03m
1 stop
Depart: Thu Jun 8 2017 Return: Mon Jun 12 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
6h 45m
1 stop
SXM
ORD
8h 27m
1 stop
Depart: Mon Jul 31 2017 Return: Wed Aug 9 2017 Trip spans 10 days
Delta
Delta
MDW
SXM
17h 24m
1 stop
SXM
MDW
9h 08m
1 stop
Depart: Fri Mar 3 2017 Return: Tue Mar 7 2017 Trip spans 5 days
Major Airline
Major Airline
ORD
SXM
2h 24m
nonstop
SXM
ORD
6h 24m
nonstop
Depart: Wed Jun 28 2017 Return: Wed Jul 5 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
6h 45m
1 stop
SXM
ORD
8h 27m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 21 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
17h 24m
1 stop
SXM
MDW
9h 08m
1 stop
Depart: Tue Jul 18 2017 Return: Tue Jul 25 2017 Trip spans 8 days
American Airlines
American Airlines
ORD
SXM
6h 45m
1 stop
SXM
ORD
8h 27m
1 stop
Depart: Wed Mar 22 2017 Return: Sun Mar 26 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
6h 49m
1 stop
SXM
MDW
30h 16m
1 stop
Depart: Mon Jul 31 2017 Return: Wed Aug 9 2017 Trip spans 10 days
American Airlines
American Airlines
ORD
SXM
8h 48m
1 stop
SXM
ORD
17h 11m
1 stop
Depart: Sat Apr 29 2017 Return: Wed May 3 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
29h 30m
1 stop
SXM
MDW
8h 24m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
6h 48m
1 stop
SXM
ORD
17h 11m
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 $511
only $520
Destination

Simpson Bay
$511