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
Students
under 26
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: Thu Feb 2 2017 Return: Mon Feb 6 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
SXM
26h 25m
1 stop
SXM
ORD
22h 52m
1 stop
Depart: Mon Jan 9 2017 Return: Wed Jan 18 2017 Trip spans 10 days
United
United
ORD
SXM
15h 10m
2 stops
SXM
ORD
24h 28m
2 stops
Depart: Mon Jan 9 2017 Return: Mon Jan 16 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
23h 27m
nonstop
SXM
ORD
8h 42m
nonstop
Depart: Mon Mar 13 2017 Return: Fri Mar 17 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
17h 40m
1 stop
SXM
ORD
17h 22m
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: Thu Feb 2 2017 Return: Sun Feb 5 2017 Trip spans 4 days
Major Airline
Major Airline
ORD
SXM
18h 56m
1 stop
SXM
ORD
27h 31m
1 stop
Depart: Wed Mar 1 2017 Return: Sun Mar 5 2017 Trip spans 5 days
JetBlue
JetBlue
ORD
SXM
16h 11m
1 stop
SXM
ORD
16h 35m
1 stop
Depart: Thu Apr 6 2017 Return: Mon Apr 10 2017 Trip spans 5 days
American Airlines
American Airlines
ORD
SXM
7h 46m
1 stop
SXM
ORD
8h 45m
1 stop
Depart: Thu Dec 29 2016 Return: Fri Jan 6 2017 Trip spans 9 days
Delta
Delta
MDW
SXM
17h 16m
1 stop
SXM
MDW
9h 11m
1 stop
Depart: Sat Jun 3 2017 Return: Sat Jun 10 2017 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
15h 22m
1 stop
SXM
ORD
20h 06m
1 stop
Depart: Sat Jun 17 2017 Return: Sat Jul 15 2017 Trip spans 29 days
American Airlines
American Airlines
ORD
SXM
7h 46m
1 stop
SXM
ORD
17h 11m
1 stop
Depart: Fri Jan 6 2017 Return: Sun Jan 15 2017 Trip spans 10 days
Delta
Delta
MDW
SXM
17h 14m
1 stop
SXM
MDW
8h 43m
1 stop
Depart: Thu Jan 12 2017 Return: Wed Jan 18 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
6h 50m
1 stop
SXM
MDW
8h 46m
1 stop
Depart: Fri Feb 24 2017 Return: Tue Feb 28 2017 Trip spans 5 days
Delta
Delta
MDW
SXM
16h 58m
1 stop
SXM
MDW
8h 28m
1 stop
Depart: Sat Dec 24 2016 Return: Sun Dec 25 2016 Trip spans 2 days
United
United
ORD
SXM
5h 10m
nonstop
SXM
ORD
5h 55m
nonstop
Depart: Sat Dec 17 2016 Return: Sat Dec 24 2016 Trip spans 8 days
Major Airline
Major Airline
ORD
SXM
25h 29m
nonstop
SXM
ORD
12h 31m
nonstop
Depart: Thu Mar 16 2017 Return: Thu Mar 23 2017 Trip spans 8 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 22m
1 stop
Depart: Wed Mar 22 2017 Return: Mon Mar 27 2017 Trip spans 6 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 22m
1 stop
Depart: Sat Apr 1 2017 Return: Tue Apr 4 2017 Trip spans 4 days
Delta
Delta
ORD
SXM
16h 30m
1 stop
SXM
ORD
8h 24m
1 stop
Depart: Tue Apr 4 2017 Return: Mon Apr 10 2017 Trip spans 7 days
Delta
Delta
MDW
SXM
6h 44m
1 stop
SXM
MDW
8h 24m
1 stop
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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 $451
only $514
Destination

Simpson Bay
$451