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Cheap flights from Chicago Midway Airport to St. Maarten from $200

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.
Delta Logo
6:04 am - 1:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 36m1 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
$489Delta
Mon, Oct 12 - Fri, Oct 16
Southwest Logo
9:20 pm - 2:05 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
15h 45m2 stops Baltimore/Washington Orlando
Southwest Logo
3:05 pm - 12:25 amSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 20m1 stop Orlando
$494Southwest
Sun, Oct 11 - Fri, Oct 16
Southwest Logo
8:40 pm - 3:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
17h 00m2 stops Baltimore/Washington 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
$494Southwest
Sun, Nov 29 - Tue, Dec 8
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:10 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 30m1 stop Atlanta Hartsfield-Jackson
$496Delta
Tue, Jan 5 - Thu, Jan 14
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:10 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 30m1 stop Atlanta Hartsfield-Jackson
$496Delta
Sun, Jan 31 - Thu, Feb 4
Delta Logo
6:00 am - 2:40 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
6h 40m1 stop Atlanta Hartsfield-Jackson
Delta Logo
1:40 pm - 10:10 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 30m1 stop Atlanta Hartsfield-Jackson
$496Delta
Sun, Jan 31 - Fri, Feb 5
Southwest Logo
5:00 am - 2:35 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
7h 35m1 stop Orlando
Southwest Logo
3:35 pm - 10:55 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
9h 20m1 stop Orlando
$496Southwest
Sun, Jan 31 - Fri, Feb 5
Delta Logo
5:25 pm - 12:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
16h 50m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl
Delta Logo
4:05 pm - 12:33 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
22h 28m2 stops New York John F Kennedy Intl Detroit Metropolitan Wayne County
$501Delta
Mon, Feb 1 - Thu, Feb 4
Delta Logo
1:00 pm - 12:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
21h 15m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
Delta Logo
1:40 pm - 10:10 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 30m1 stop Atlanta Hartsfield-Jackson
$501Delta
Mon, Feb 1 - Thu, Feb 4
Delta Logo
1:00 pm - 12:15 pmMDW  Chicago Midway-SXM Simpson Bay Princess Juliana
21h 15m2 stops Detroit Metropolitan Wayne County New York John F Kennedy Intl
Delta Logo
1:40 pm - 10:10 pmSXM  Simpson Bay Princess Juliana-MDW Chicago Midway
10h 30m1 stop Atlanta Hartsfield-Jackson
$501Delta
Mon, Feb 1 - Fri, Feb 5

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Delta flights from Chicago Midway Airport to St. Maarten

Our best Delta deals on Chicago Midway Airport to St. Maarten flight tickets
Delta
Oct 12
MDW6:04 amChicago Midway
6h 36m
1 stop
SXM1:40 pmSimpson Bay Princess Juliana
Oct 16
SXM3:05 pmSimpson Bay Princess Juliana
8h 28m
1 stop
MDW10:33 pmChicago Midway
$489
Delta
Oct 11
MDW6:04 amChicago Midway
6h 36m
1 stop
SXM1:40 pmSimpson Bay Princess Juliana
Oct 16
SXM3:05 pmSimpson Bay Princess Juliana
8h 28m
1 stop
MDW10:33 pmChicago Midway
$524
Delta
Oct 11
MDW6:04 amChicago Midway
6h 36m
1 stop
SXM1:40 pmSimpson Bay Princess Juliana
Oct 16
SXM3:05 pmSimpson Bay Princess Juliana
8h 28m
1 stop
MDW10:33 pmChicago Midway
$557

Southwest flights from Chicago Midway Airport to St. Maarten

Our best Southwest deals on Chicago Midway Airport to St. Maarten flight tickets
Southwest
Nov 29
MDW8:40 pmChicago Midway
17h 00m
2 stops
SXM3:40 pmSimpson Bay Princess Juliana
Dec 8
SXM3:20 pmSimpson Bay Princess Juliana
16h 20m
2 stops
MDW5:40 amChicago Midway
$494
Southwest
Oct 11
MDW9:20 pmChicago Midway
15h 45m
2 stops
SXM2:05 pmSimpson Bay Princess Juliana
Oct 16
SXM3:05 pmSimpson Bay Princess Juliana
17h 25m
2 stops
MDW7:30 amChicago Midway
$529
Southwest
Dec 30
MDW9:05 pmChicago Midway
15h 15m
2 stops
SXM2:20 pmSimpson Bay Princess Juliana
Jan 8
SXM3:35 pmSimpson Bay Princess Juliana
20h 55m
2 stops
MDW10:30 amChicago Midway
$536

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to St. Maarten that are best for you.

Fly from

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Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Mon 10/12

6:04 am-1:40 pm

1 stop6h 36m

Simpson Bay Princess Juliana

Fri 10/16

3:05 pm-10:33 pm

1 stop8h 28m

$489

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 10/11

9:20 pm-2:05 pm

2 stops15h 45m

Simpson Bay Princess Juliana

Fri 10/16

3:05 pm-12:25 am

1 stop10h 20m

$494

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 11/29

8:40 pm-3:40 pm

2 stops17h 00m

Simpson Bay Princess Juliana

Tue 12/8

3:20 pm-5:40 am

2 stops16h 20m

$494

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Tue 1/5

6:00 am-2:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Thu 1/14

1:40 pm-10:10 pm

1 stop10h 30m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 1/31

6:00 am-2:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Thu 2/4

1:40 pm-10:10 pm

1 stop10h 30m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 1/31

6:00 am-2:40 pm

1 stop6h 40m

Simpson Bay Princess Juliana

Fri 2/5

1:40 pm-10:10 pm

1 stop10h 30m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Sun 1/31

5:00 am-2:35 pm

1 stop7h 35m

Simpson Bay Princess Juliana

Fri 2/5

3:35 pm-10:55 pm

1 stop9h 20m

$496

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Mon 2/1

5:25 pm-12:15 pm

2 stops16h 50m

Simpson Bay Princess Juliana

Thu 2/4

4:05 pm-12:33 pm

2 stops22h 28m

$501

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Mon 2/1

1:00 pm-12:15 pm

2 stops21h 15m

Simpson Bay Princess Juliana

Thu 2/4

1:40 pm-10:10 pm

1 stop10h 30m

$501

ChicagoSimpson Bay

MDW Chicago Midway - SXM Simpson Bay Princess Juliana

MDWSXM

Chicago Midway

Mon 2/1

1:00 pm-12:15 pm

2 stops21h 15m

Simpson Bay Princess Juliana

Fri 2/5

1:40 pm-10:10 pm

1 stop10h 30m

$501

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 34% 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

$200

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 $200. The best round-trip flight deal from Chicago Midway Airport to St. Maarten found on momondo in the last 72 hours is $489.
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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