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Cheap flights from Chicago Midway Airport to St. Maarten from $118

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to St. Maarten departing on 7/20. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to St. Maarten

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$325Southwest
Fri, Aug 28 - Thu, Sep 3
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$385Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 7:35 am
SXM
-
MDW
17h 30m
2 stops
$390Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 12:55 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$420Southwest
Sat, Aug 15 - Thu, Aug 20
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 7:35 am
SXM
-
MDW
17h 30m
2 stops
$425Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$445Southwest
Thu, Sep 10 - Mon, Sep 14
Southwest Logo
5:00 am - 12:55 pm
MDW
-
SXM
6h 55m
1 stop
Southwest Logo
1:55 pm - 8:55 pm
SXM
-
MDW
8h 00m
1 stop
$448Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
8:15 pm - 12:55 pm
MDW
-
SXM
15h 40m
2 stops
Southwest Logo
3:05 pm - 7:35 am
SXM
-
MDW
17h 30m
2 stops
$450Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
7:10 pm - 2:05 pm
MDW
-
SXM
17h 55m
2 stops
Southwest Logo
3:05 pm - 12:20 am
SXM
-
MDW
10h 15m
1 stop
$457Southwest
Sat, Oct 17 - Mon, Oct 19
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
Southwest Logo
3:05 pm - 10:40 pm
SXM
-
MDW
8h 35m
1 stop
$475Southwest
Fri, Aug 14 - Fri, Aug 21

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Southwest flights from Chicago Midway Airport to St. Maarten

Our best Southwest deals on Chicago Midway Airport to St. Maarten flight tickets
Southwest
Aug 28
MDW5:00 amChicago Midway
8h 05m
1 stop
SXM2:05 pmSimpson Bay Princess Juliana
Sep 3
SXM3:05 pmSimpson Bay Princess Juliana
8h 35m
1 stop
MDW10:40 pmChicago Midway
$325
Southwest
Aug 14
MDW5:00 amChicago Midway
8h 05m
1 stop
SXM2:05 pmSimpson Bay Princess Juliana
Aug 21
SXM3:05 pmSimpson Bay Princess Juliana
8h 35m
1 stop
MDW10:40 pmChicago Midway
$385
Southwest
Aug 14
MDW5:00 amChicago Midway
8h 05m
1 stop
SXM2:05 pmSimpson Bay Princess Juliana
Aug 21
SXM3:05 pmSimpson Bay Princess Juliana
17h 30m
2 stops
MDW7:35 amChicago Midway
$390

Delta flights from Chicago Midway Airport to St. Maarten

Our best Delta deals on Chicago Midway Airport to St. Maarten flight tickets
Delta
Oct 24
MDW6:00 amChicago Midway
6h 49m
1 stop
SXM1:49 pmSimpson Bay Princess Juliana
Oct 31
SXM3:14 pmSimpson Bay Princess Juliana
8h 11m
1 stop
MDW10:25 pmChicago Midway
$665
Delta
Jul 28
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM1:55 pmSimpson Bay Princess Juliana
Aug 7
SXM3:18 pmSimpson Bay Princess Juliana
22h 21m
2 stops
MDW12:39 pmChicago Midway
$670
Delta
Jul 16
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM1:55 pmSimpson Bay Princess Juliana
Jul 21
SXM3:20 pmSimpson Bay Princess Juliana
7h 55m
1 stop
MDW10:15 pmChicago Midway
$930

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to St. Maarten that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/28

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Thu 9/3

3:05 pm-10:40 pm

1 stop8h 35m

$325

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/14

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 8/21

3:05 pm-10:40 pm

1 stop8h 35m

$385

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/14

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 8/21

3:05 pm-7:35 am

2 stops17h 30m

$390

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/15

5:00 am-12:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 8/20

3:05 pm-10:40 pm

1 stop8h 35m

$420

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/14

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 8/21

3:05 pm-7:35 am

2 stops17h 30m

$425

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 9/10

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Mon 9/14

3:05 pm-10:40 pm

1 stop8h 35m

$445
Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/15

5:00 am-12:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 8/22

1:55 pm-8:55 pm

1 stop8h 00m

$448

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/14

8:15 pm-12:55 pm

2 stops15h 40m

Simpson Bay Princess Juliana

Fri 8/21

3:05 pm-7:35 am

2 stops17h 30m

$450

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 10/17

7:10 pm-2:05 pm

2 stops17h 55m

Simpson Bay Princess Juliana

Mon 10/19

3:05 pm-12:20 am

1 stop10h 15m

$457

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 8/14

5:00 am-2:05 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Fri 8/21

3:05 pm-10:40 pm

1 stop8h 35m

$475

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to St. Maarten from

How to get the cheapest flight ticket from Chicago Midway Airport to St. Maarten

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Chicago Midway Airport to St. Maarten flights?

You could potentially save up to 53% on your flight if you consider stops on a Chicago Midway Airport to St. Maarten flight.

Cheap Chicago Midway Airport to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to St. Maarten

Fastest flight time

6h 40m

Direct flights

None
The fastest flight from Chicago Midway Airport to St. Maarten takes 6h 40m
There are no direct flights from Chicago Midway Airport to St. Maarten. There are no popular flight routes from Chicago Midway Airport to St. Maarten.
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Frequently asked questions about flying from Chicago Midway Airport to St. Maarten

  • When did momondo last update prices for flights from Chicago Midway Airport to St. Maarten?

    Prices for flights from Chicago Midway Airport to St. Maarten are refreshed on a daily basis.

  • How old do you have to be to fly from Chicago Midway Airport to St. Maarten?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to St. Maarten.

  • What documentation or ID do you need to fly to St. Maarten?

    The necessary travel and health documents for your St. Maarten trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to St. Maarten?

Finding the right flight to St. Maarten from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to St. Maarten quick and easy, saving you time and money.

Can I find flights from Chicago to St. Maarten with flexible booking policies on momondo?

Flights from Chicago to St. Maarten with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Chicago to St. Maarten?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to St. Maarten.

I’m not ready to book a flight from Chicago to St. Maarten right now. Can momondo alert me if prices change?

If you are simply researching potential flights to St. Maarten, momondo offers a useful price alert feature which will track prices for flights to St. Maarten from Chicago and alert you when they change.

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Find better results for your trip to St. Maarten

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Popular flights according to clicks in the last 7 days on momondo
Flights to Simpson Bayfrom $306