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 October 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.

$213 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

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One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:00 am - 2:55 pmMDW-SXM

6h 55m1 stop

4:20 pm - 11:40 pmSXM-MDW

9h 20m1 stop

$433Delta

Find Deal

Mon, Nov 10 - Fri, Nov 14

6:00 am - 3:20 pmMDW-SXM

7h 20m1 stop

4:30 pm - 11:25 pmSXM-MDW

8h 55m1 stop

$483Frontier

Find Deal

Sat, Jan 24 - Sat, Jan 31

6:00 am - 3:20 pmMDW-SXM

7h 20m1 stop

4:30 pm - 11:25 pmSXM-MDW

8h 55m1 stop

$489Frontier

Find Deal

Sat, Jan 24 - Sat, Jan 31

8:42 pm - 1:30 pmMDW-SXM

14h 48m1 stop

2:40 pm - 10:12 pmSXM-MDW

9h 32m1 stop

$499Frontier

Find Deal

Fri, Dec 5 - Sat, Dec 13

6:00 am - 3:20 pmMDW-SXM

7h 20m1 stop

4:30 pm - 11:25 pmSXM-MDW

8h 55m1 stop

$519Frontier

Find Deal

Sat, Feb 21 - Sat, Feb 28

6:00 am - 2:28 pmMDW-SXM

6h 28m1 stop

1:45 pm - 10:22 pmSXM-MDW

10h 37m1 stop

$587Delta

Find Deal

Wed, Dec 17 - Tue, Dec 23

8:42 pm - 2:10 pmMDW-SXM

15h 28m2 stops

1:25 pm - 10:05 amSXM-MDW

22h 40m1 stop

$592Multiple Airlines

Find Deal

Fri, Dec 5 - Sat, Dec 13

4:15 pm - 3:21 pmMDW-SXM

21h 06m1 stop

3:15 pm - 9:17 amSXM-MDW

20h 02m2 stops

$607Multiple Airlines

Find Deal

Mon, Dec 8 - Mon, Dec 15

9:59 am - 3:21 pmMDW-SXM

27h 22m2 stops

4:20 pm - 6:18 pmSXM-MDW

27h 58m2 stops

$737WestJet

Find Deal

Sat, Dec 13 - Wed, Dec 17

1:47 pm - 3:21 pmMDW-SXM

23h 34m2 stops

4:20 pm - 1:07 pmSXM-MDW

22h 47m2 stops

$829WestJet

Find Deal

Mon, Nov 10 - Fri, Nov 14

Delta flights from Chicago Midway Airport to St. Maarten

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

Delta

Nov 10

MDW6:00 amChicago Midway

6h 55m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Nov 14

SXM4:20 pmSimpson Bay Princess Juliana

9h 20m

1 stop

MDW11:40 pmChicago Midway

$433

Find similar

Delta

Dec 17

MDW6:00 amChicago Midway

6h 28m

1 stop

SXM2:28 pmSimpson Bay Princess Juliana

Dec 23

SXM1:45 pmSimpson Bay Princess Juliana

10h 37m

1 stop

MDW10:22 pmChicago Midway

$587

Find similar

Delta

Nov 26

MDW6:00 amChicago Midway

6h 55m

1 stop

SXM2:55 pmSimpson Bay Princess Juliana

Dec 6

SXM3:25 pmSimpson Bay Princess Juliana

10h 22m

1 stop

MDW11:47 pmChicago Midway

$612

Find similar

Frontier flights from Chicago Midway Airport to St. Maarten

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

Frontier

Jan 24

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Jan 31

SXM4:30 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MDW11:25 pmChicago Midway

$483

Find similar

Frontier

Jan 24

MDW6:00 amChicago Midway

7h 20m

1 stop

SXM3:20 pmSimpson Bay Princess Juliana

Jan 31

SXM4:30 pmSimpson Bay Princess Juliana

8h 55m

1 stop

MDW11:25 pmChicago Midway

$489

Find similar

Frontier

Dec 5

MDW8:42 pmChicago Midway

14h 48m

1 stop

SXM1:30 pmSimpson Bay Princess Juliana

Dec 13

SXM2:40 pmSimpson Bay Princess Juliana

9h 32m

1 stop

MDW10:12 pmChicago Midway

$499

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

Mon 11/10

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-11:40 pm

1 stop9h 20m

$433

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/31

4:30 pm-11:25 pm

1 stop8h 55m

$483

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 1/31

4:30 pm-11:25 pm

1 stop8h 55m

$489

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/5

8:42 pm-1:30 pm

1 stop14h 48m

Simpson Bay Princess Juliana

Sat 12/13

2:40 pm-10:12 pm

1 stop9h 32m

$499

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

$519

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/17

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-10:22 pm

1 stop10h 37m

$587

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/5

8:42 pm-2:10 pm

2 stops15h 28m

Simpson Bay Princess Juliana

Sat 12/13

1:25 pm-10:05 am

1 stop22h 40m

$592

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 12/8

4:15 pm-3:21 pm

1 stop21h 06m

Simpson Bay Princess Juliana

Mon 12/15

3:15 pm-9:17 am

2 stops20h 02m

$607

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 12/13

9:59 am-3:21 pm

2 stops27h 22m

Simpson Bay Princess Juliana

Wed 12/17

4:20 pm-6:18 pm

2 stops27h 58m

$737

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 11/10

1:47 pm-3:21 pm

2 stops23h 34m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-1:07 pm

2 stops22h 47m

$829

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

What is the cheapest airline that flies from Chicago Midway to St. Maarten?

Frontier, Delta, and WestJet are the most popular carriers operating from Chicago Midway to St. Maarten

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

Direct flights	None

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 October 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 $622	Free Cancellation	Rating 7.9 7,982 reviews		Search Delta flights

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

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Popular cities in St. Maarten

Flights to Simpson Bayfrom $260

Cheap flights from Chicago Midway Airport to St. Maarten from $213

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

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

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Delta flights from Chicago Midway Airport to St. Maarten

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

Frontier flights from Chicago Midway Airport to St. Maarten

Our best Frontier 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.

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

What is the cheapest airline that flies from Chicago Midway to St. Maarten?

Frontier, Delta, and WestJet are the most popular carriers operating from Chicago Midway to St. Maarten

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

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

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