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Cheap flights from Chicago Midway Airport to St. Maarten from $242

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 11/6. 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
8:25 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
3:20 pm - 1:05 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
11h 45m2 stops Orlando Houston Hobby
$472Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
8:25 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
4:40 pm - 11:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 25m1 stop Baltimore/Washington
$472Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
5:05 am - 2:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 10m1 stop Baltimore/Washington
Southwest Logo
3:20 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 20m2 stops Orlando Las Vegas Harry Reid Intl
$489Southwest
Fri, Nov 27 - Thu, Dec 3
Southwest Logo
5:10 am - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
8h 30m1 stop Orlando
Southwest Logo
3:20 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 35m1 stop Orlando
$520Southwest
Sun, Nov 1 - Thu, Nov 5
Southwest Logo
5:20 am - 2:20 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 00m1 stop Orlando
Southwest Logo
3:20 pm - 5:40 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
16h 20m2 stops Orlando Las Vegas Harry Reid Intl
$525Southwest
Wed, Dec 2 - Mon, Dec 7
Southwest Logo
8:25 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
3:15 pm - 8:55 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
19h 40m2 stops Orlando Baltimore/Washington
$525Southwest
Thu, Nov 12 - Fri, Nov 20
Southwest Logo
4:00 pm - 1:30 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
19h 30m2 stops Nashville Intl Baltimore/Washington
Southwest Logo
3:20 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 45m2 stops Orlando Las Vegas Harry Reid Intl
$525Southwest
Fri, Nov 27 - Thu, Dec 3
Southwest Logo
6:25 pm - 2:05 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
18h 40m2 stops Denver Intl Orlando
Southwest Logo
3:05 pm - 12:20 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 15m1 stop Orlando
$531Southwest
Thu, Oct 8 - Thu, Oct 15
Southwest Logo
8:50 pm - 2:20 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
15h 30m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
3:20 pm - 12:05 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 45m2 stops Orlando Las Vegas Harry Reid Intl
$531Southwest
Thu, Dec 3 - Mon, Dec 7
Delta Logo
6:05 am - 1:53 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 48m1 stop Atlanta Hartsfield-Jackson
Delta Logo
3:05 pm - 10:33 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
8h 28m1 stop Atlanta Hartsfield-Jackson
$665Delta
Wed, Sep 30 - Wed, Oct 7

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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
Nov 1
MDW8:25 pmChicago Midway
17h 15m
2 stops
SXM3:40 pmSimpson Bay Princess Juliana
Nov 5
SXM3:20 pmSimpson Bay Princess Juliana
11h 45m
2 stops
MDW1:05 amChicago Midway
$472
Southwest
Nov 27
MDW5:05 amChicago Midway
7h 10m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
Dec 3
SXM3:20 pmSimpson Bay Princess Juliana
16h 20m
2 stops
MDW5:40 amChicago Midway
$489
Southwest
Nov 1
MDW5:10 amChicago Midway
8h 30m
1 stop
SXM3:40 pmSimpson Bay Princess Juliana
Nov 5
SXM3:20 pmSimpson Bay Princess Juliana
9h 35m
1 stop
MDW10:55 pmChicago Midway
$520

Delta flights from Chicago Midway Airport to St. Maarten

Our best Delta deals on Chicago Midway Airport to St. Maarten flight tickets
Delta
Sep 30
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 7
SXM3:05 pmSimpson Bay Princess Juliana
8h 28m
1 stop
MDW10:33 pmChicago Midway
$665
Delta
Nov 23
MDW1:22 pmChicago Midway
23h 23m
2 stops
SXM2:45 pmSimpson Bay Princess Juliana
Dec 2
SXM4:10 pmSimpson Bay Princess Juliana
19h 32m
2 stops
MDW9:42 amChicago Midway
$670
Delta
Sep 30
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Oct 5
SXM3:18 pmSimpson Bay Princess Juliana
8h 26m
1 stop
MDW10:44 pmChicago Midway
$675

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 August 18, 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 Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

8:25 pm-3:40 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Thu 11/5

3:20 pm-1:05 am

2 stops11h 45m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

8:25 pm-3:40 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Thu 11/5

4:40 pm-11:05 pm

1 stop8h 25m

$472

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Fri 11/27

5:05 am-2:15 pm

1 stop7h 10m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-5:40 am

2 stops16h 20m

$489

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/1

5:10 am-3:40 pm

1 stop8h 30m

Simpson Bay Princess Juliana

Thu 11/5

3:20 pm-10:55 pm

1 stop9h 35m

$520

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Wed 12/2

5:20 am-2:20 pm

1 stop7h 00m

Simpson Bay Princess Juliana

Mon 12/7

3:20 pm-5:40 am

2 stops16h 20m

$525

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Thu 11/12

8:25 pm-3:40 pm

2 stops17h 15m

Simpson Bay Princess Juliana

Fri 11/20

3:15 pm-8:55 am

2 stops19h 40m

$525

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Fri 11/27

4:00 pm-1:30 pm

2 stops19h 30m

Simpson Bay Princess Juliana

Thu 12/3

3:20 pm-12:05 pm

2 stops22h 45m

$525

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Thu 10/8

6:25 pm-2:05 pm

2 stops18h 40m

Simpson Bay Princess Juliana

Thu 10/15

3:05 pm-12:20 am

1 stop10h 15m

$531

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Thu 12/3

8:50 pm-2:20 pm

2 stops15h 30m

Simpson Bay Princess Juliana

Mon 12/7

3:20 pm-12:05 pm

2 stops22h 45m

$531
Quickest round-trip

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Wed 9/30

6:05 am-1:53 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Wed 10/7

3:05 pm-10:33 pm

1 stop8h 28m

$665

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 30% 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

Best Price Found

$242

Fastest flight time

6h 36m

Direct flights

None
The best one-way flight to St. Maarten from Chicago Midway Airport in the past 72 hours is $242. The best round-trip flight deal from Chicago Midway Airport to St. Maarten found on momondo in the last 72 hours is $472.
The fastest flight from Chicago Midway Airport to St. Maarten takes 6h 36m
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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Flights to Simpson Bayfrom $311