How do I get Price Alerts for flights from Chicago Midway Airport to St. Maarten?

Price Alerts will notify you by email when the price for flights to St. Maarten from Chicago Midway Airport decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.

How can I save money on flights from Chicago Midway Airport to St. Maarten with momondo?

Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore” . Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

How does momondo find its flight prices?

We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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 many operators does momondo search for flights from Chicago Midway Airport to St. Maarten?

As of December 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to St. Maarten.

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.

$100 Cheap Flights from Chicago Midway Airport to St. Maarten in 2025/26

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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$308Frontier

Sat, Feb 21 - Sat, Feb 28

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$359Frontier

Sat, Feb 14 - Sat, Feb 28

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$379Frontier

Sat, Feb 14 - Sat, Feb 28

6:00 am - 2:40 pm

MDW

SXM

7h 40m1 stop

3:40 pm - 11:42 pm

SXM

MDW

9h 02m1 stop

$474Frontier

Sat, Apr 4 - Sat, Apr 11

6:00 am - 2:40 pm

MDW

SXM

7h 40m1 stop

3:40 pm - 11:42 pm

SXM

MDW

9h 02m1 stop

$497Frontier

Sat, Apr 4 - Sat, Apr 11

6:00 am - 2:55 pm

MDW

SXM

6h 55m1 stop

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$501Delta

Sun, Jan 25 - Fri, Jan 30

5:31 pm - 12:30 pm

MDW

SXM

16h 59m2 stops

1:55 pm - 10:07 pm

SXM

MDW

10h 12m1 stop

$506Delta

Wed, Jan 7 - Wed, Jan 14

6:45 am - 4:03 pm

MDW

SXM

7h 18m1 stop

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$531Delta

Sat, Jan 17 - Fri, Jan 23

4:15 pm - 12:15 pm

MDW

SXM

18h 00m1 stop

3:15 pm - 10:34 am

SXM

MDW

21h 19m2 stops

$536Multiple Airlines

Mon, Jan 5 - Mon, Jan 12

6:45 am - 4:03 pm

MDW

SXM

7h 18m1 stop

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$561Delta

Sat, Jan 17 - Sat, Jan 24

Frontier flights from Chicago Midway Airport to St. Maarten

Our best Frontier deals on Chicago Midway Airport to St. Maarten 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

$308

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

$359

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

$379

Find similar

Delta flights from Chicago Midway Airport to St. Maarten

Our best Delta deals on Chicago Midway Airport to St. Maarten flight tickets

Delta

Jan 25

MDW6:00 amChicago Midway

6h 55m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Jan 30

SXM1:55 pmSimpson Bay Princess Juliana

10h 27m

1 stop

MDW10:22 pmChicago Midway

$501

Find similar

Delta

Jan 7

MDW5:31 pmChicago Midway

16h 59m

2 stops

SXM12:30 pmSimpson Bay Princess Juliana

Jan 14

SXM1:55 pmSimpson Bay Princess Juliana

10h 12m

1 stop

MDW10:07 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 27m

2 stops

MDW8:49 amChicago Midway

$522

Find similar

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

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

$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

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

$379

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/4

6:00 am-2:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Sat 4/11

3:40 pm-11:42 pm

1 stop9h 02m

$474

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 4/4

6:00 am-2:40 pm

1 stop7h 40m

Simpson Bay Princess Juliana

Sat 4/11

3:40 pm-11:42 pm

1 stop9h 02m

$497

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

$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

Sat 1/17

6:45 am-4:03 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Fri 1/23

1:55 pm-10:22 pm

1 stop10h 27m

$531

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 1/5

4:15 pm-12:15 pm

1 stop18h 00m

Simpson Bay Princess Juliana

Mon 1/12

3:15 pm-10:34 am

2 stops21h 19m

$536

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/17

6:45 am-4:03 pm

1 stop7h 18m

Simpson Bay Princess Juliana

Sat 1/24

1:55 pm-10:22 pm

1 stop10h 27m

$561

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 50m
Direct flights	None

The fastest flight from Chicago Midway Airport to St. Maarten takes 6h 50m

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.

Search flight deals

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 many operators does momondo search for flights from Chicago Midway Airport to St. Maarten?
As of December 2025, there is 1 operator available to choose from for flights from Chicago Midway Airport to St. Maarten.
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.

Best airlines flying from Chicago Midway Airport to St. Maarten

Compare and see reviews for airlines that fly from Chicago Midway Airport to St. Maarten with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $512	Free Cancellation	Rating 7.9 8,007 reviews		Search Delta flights

How do I get Price Alerts for flights from Chicago Midway Airport to St. Maarten?
Price Alerts will notify you by email when the price for flights to St. Maarten from Chicago Midway Airport decreases. To activate this, select your desired travel dates and search for offers. While browsing through offers you’ll see the Price Alert widget toggle. Click it to turn on notifications.
How can I save money on flights from Chicago Midway Airport to St. Maarten with momondo?
Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.
How does momondo find its flight prices?
We aggregate our prices from over 700+ competitors from airlines to OTAs. We operate in over 30 markets worldwide to show you a wide range of travel options.

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.

An easier way to manage your St. Maarten trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

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Fri 1/9

Fri 1/16

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Find better results for your trip to St. Maarten

Popular cities in St. Maarten

Flights to Simpson Bayfrom $175

Cheap flights from Chicago Midway Airport to St. Maarten from $100

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

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

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Frontier flights from Chicago Midway Airport to St. Maarten

Our best Frontier deals on Chicago Midway Airport to St. Maarten flight tickets

Delta flights from Chicago Midway Airport to St. Maarten

Our best Delta deals on Chicago Midway Airport to St. Maarten flight tickets

momondo Fare Finder

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

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

Direct flights

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

How many operators does momondo search for flights from Chicago Midway Airport to St. Maarten?

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

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

Best airlines flying from Chicago Midway Airport to St. Maarten

Compare and see reviews for airlines that fly from Chicago Midway Airport to St. Maarten with momondo

How do I get Price Alerts for flights from Chicago Midway Airport to St. Maarten?

How can I save money on flights from Chicago Midway Airport to St. Maarten with momondo?

How does momondo find its flight prices?

Why use momondo?

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

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

How can momondo help me find flights 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?

An easier way to manage your St. Maarten trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to St. Maarten

Popular cities in St. Maarten

Popular flights according to clicks in the last 7 days on momondo