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Cheap flights from Chicago Midway Airport to Saint Martin Island from $100

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 Saint Martin Island departing on 2/21. 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
0 bags

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Find the cheapest flights from Chicago Midway Airport to Saint Martin Island

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$287Frontier
Sat, Feb 21 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$308Frontier
Sat, Feb 14 - Sat, Feb 28
Frontier Logo
6:00 am - 3:20 pm
MDW
-
SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pm
SXM
-
MDW
8h 55m1 stop
$359Frontier
Sat, Feb 14 - Sat, Feb 28
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$501Delta
Sun, Feb 1 - Fri, Feb 6
Delta Logo
5:31 pm - 12:30 pm
MDW
-
SXM
16h 59m2 stops
Delta Logo
1:55 pm - 10:07 pm
SXM
-
MDW
10h 12m1 stop
$506Delta
Wed, Jan 7 - Wed, Jan 14
Multiple Airlines Logo
5:10 pm - 2:10 pm
MDW
-
SXM
19h 00m2 stops
Multiple Airlines Logo
4:20 pm - 10:10 am
SXM
-
MDW
19h 50m1 stop
$553Multiple Airlines
Wed, Jan 7 - Wed, Jan 14
Delta Logo
6:00 am - 2:55 pm
MDW
-
SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pm
SXM
-
MDW
10h 27m1 stop
$581Delta
Sun, Jan 25 - Fri, Jan 30
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:55 pm - 10:07 pm
SXM
-
MDW
10h 12m1 stop
$584Delta
Wed, Dec 31 - Fri, Jan 9
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:38 pm - 10:42 pm
SXM
-
MDW
11h 04m1 stop
$614Delta
Fri, Feb 27 - Fri, Mar 6
Delta Logo
6:00 am - 2:50 pm
MDW
-
SXM
6h 50m1 stop
Delta Logo
1:38 pm - 10:44 pm
SXM
-
MDW
11h 06m1 stop
$661Delta
Tue, Feb 17 - Tue, Feb 24

Frontier flights from Chicago Midway Airport to Saint Martin Island

Our best Frontier deals on Chicago Midway Airport to Saint Martin Island flight tickets
Frontier
Feb 21
MDW6:00 amChicago Midway
7h 20m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Feb 28
SXM4:30 pmSimpson Bay Princess Juliana
8h 55m
1 stop
MDW11:25 pmChicago Midway
$287
Find similar
Frontier
Feb 14
MDW6:00 amChicago Midway
7h 20m
1 stop
SXM3:20 pmSimpson Bay Princess Juliana
Feb 28
SXM4:30 pmSimpson Bay Princess Juliana
8h 55m
1 stop
MDW11:25 pmChicago Midway
$308
Find similar
Frontier
Apr 4
MDW6:00 amChicago Midway
7h 40m
1 stop
SXM2:40 pmSimpson Bay Princess Juliana
Apr 11
SXM3:40 pmSimpson Bay Princess Juliana
9h 02m
1 stop
MDW11:42 pmChicago Midway
$457
Find similar

Delta flights from Chicago Midway Airport to Saint Martin Island

Our best Delta deals on Chicago Midway Airport to Saint Martin Island flight tickets
Delta
Feb 1
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Feb 6
SXM1:55 pmSimpson Bay Princess Juliana
10h 27m
1 stop
MDW10:22 pmChicago Midway
$501
Find similar
Delta
Dec 22
MDW9:29 amChicago Midway
27h 21m
2 stops
SXM2:50 pmSimpson Bay Princess Juliana
Dec 31
SXM1:45 pmSimpson Bay Princess Juliana
10h 37m
1 stop
MDW10:22 pmChicago Midway
$506
Find similar
Delta
Dec 14
MDW6:00 amChicago Midway
6h 28m
1 stop
SXM2:28 pmSimpson Bay Princess Juliana
Dec 20
SXM5:22 pmSimpson Bay Princess Juliana
17h 43m
1 stop
MDW9:05 amChicago Midway
$524
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Saint Martin Island 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 December 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Saint Martin Island that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/21

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$287

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/14

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$308

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/14

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 2/28

4:30 pm-11:25 pm

1 stop8h 55m

$359

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/1

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 2/6

1:55 pm-10:22 pm

1 stop10h 27m

$501

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/7

5:31 pm-12:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

Wed 1/14

1:55 pm-10:07 pm

1 stop10h 12m

$506

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/7

5:10 pm-2:10 pm

2 stops19h 00m

Simpson Bay Princess Juliana

Wed 1/14

4:20 pm-10:10 am

1 stop19h 50m

$553

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 1/30

1:55 pm-10:22 pm

1 stop10h 27m

$581

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/31

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 1/9

1:55 pm-10:07 pm

1 stop10h 12m

$584

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/27

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Fri 3/6

1:38 pm-10:42 pm

1 stop11h 04m

$614

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 2/17

6:00 am-2:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Tue 2/24

1:38 pm-10:44 pm

1 stop11h 06m

$661

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 Saint Martin Island from

How to get the cheapest flight ticket from Chicago Midway Airport to Saint Martin Island

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 Saint Martin Island flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Saint Martin Island.

Cheap Chicago Midway Airport to Saint Martin Island flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Saint Martin Island

Fastest flight time

6h 50m

Direct flights

None
The fastest flight from Chicago Midway Airport to Saint Martin Island takes 6h 50m
There are no direct flights from Chicago Midway Airport to Saint Martin Island. There are no popular flight routes from Chicago Midway Airport to Saint Martin Island.
Search flight deals

  • When did momondo last update prices for flights from Chicago Midway Airport to Saint Martin Island?

    Prices for flights from Chicago Midway Airport to Saint Martin Island were last updated today.

  • How many operators does momondo search for flights from Chicago Midway Airport to Saint Martin Island?

  • How old do you have to be to fly from Chicago Midway Airport to Saint Martin Island?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Chicago Midway Airport to Saint Martin Island.

  • What documentation or ID do you need to fly to Saint Martin Island?

    The required travel and health documents for your Saint Martin Island trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Saint Martin Island. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Chicago Midway Airport to Saint Martin Island?

Best airlines flying from Chicago Midway Airport to Saint Martin Island

Compare and see reviews for airlines that fly from Chicago Midway Airport to Saint Martin Island with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $512Free CancellationRating
7.9
8,007 reviews
Search Delta flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Saint Martin Island?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Saint Martin Island from Chicago.

Can I find flights from Chicago to Saint Martin Island with flexible booking policies on momondo?

Flights from Chicago to Saint Martin Island 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 Saint Martin Island?

Once all potential Chicago to Saint Martin Island flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Saint Martin Island from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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