What airlines fly to St. Maarten?

American Airlines, United Airlines and Spirit Airlines are the top three most popular airlines that fly to St. Maarten from Chicago according to our data. American Airlines is the first choice among our users, with 52% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 4 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

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

Spirit Airlines, Copa Airlines, and Delta are the most popular carriers operating from Chicago to St. Maarten

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

Prices for flights from Chicago to St. Maarten were last updated today.

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

As of August 2025, there are 4 operators available to choose from for flights from Chicago to St. Maarten.

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

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to St. Maarten.

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

The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$139 Cheap Flights from Chicago to St. Maarten in 2025

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Find the cheapest flights from Chicago to St. Maarten

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

5:05 am - 2:00 pmORD-SXM

7h 55m1 stop

3:05 pm - 10:48 pmSXM-ORD

8h 43m1 stop

$296Spirit Airlines

Find Deal

Sat, Sep 6 - Sat, Sep 13

5:05 am - 2:00 pmORD-SXM

7h 55m1 stop

3:05 pm - 10:48 pmSXM-ORD

8h 43m1 stop

$317Spirit Airlines

Find Deal

Sat, Sep 6 - Sat, Sep 13

10:27 am - 8:12 amORD-SXM

20h 45m2 stops

3:05 pm - 10:48 pmSXM-ORD

8h 43m1 stop

$420

Find Deal

Tue, Sep 23 - Mon, Sep 29

6:07 pm - 1:59 pmORD-SXM

18h 52m2 stops

3:05 pm - 6:24 pmSXM-ORD

28h 19m1 stop

$425

Find Deal

Thu, Oct 16 - Mon, Oct 20

7:00 am - 4:38 pmORD-SXM

7h 38m1 stop

5:44 pm - 8:52 pmSXM-ORD

29h 08m1 stop

$443JetBlue

Find Deal

Tue, Nov 4 - Thu, Nov 13

7:00 am - 4:38 pmORD-SXM

7h 38m1 stop

5:44 pm - 5:55 pmSXM-ORD

26h 11m2 stops

$458JetBlue

Find Deal

Tue, Nov 4 - Thu, Nov 13

6:00 am - 2:35 pmMDW-SXM

6h 35m1 stop

4:00 pm - 9:44 pmSXM-MDW

7h 44m1 stop

$677Delta

Find Deal

Fri, Dec 5 - Sat, Dec 13

6:00 am - 2:56 pmMDW-SXM

6h 56m1 stop

1:45 pm - 9:46 pmSXM-MDW

10h 01m1 stop

$767Delta

Find Deal

Sat, Jan 24 - Sun, Feb 1

1:48 pm - 3:21 pmMDW-SXM

23h 33m2 stops

4:20 pm - 1:09 pmSXM-MDW

22h 49m2 stops

$3,140WestJet

Find Deal

Wed, Nov 5 - Tue, Nov 11

9:15 am - 2:19 pmMDW-SXM

28h 04m2 stops

2:10 pm - 9:36 pmSXM-MDW

32h 26m2 stops

$3,165WestJet

Find Deal

Wed, Sep 10 - Sun, Sep 14

Spirit Airlines flights from Chicago to St. Maarten

Our best Spirit Airlines deals on Chicago to St. Maarten flight tickets

Spirit Airlines

Sep 6

ORD5:05 amChicago O'Hare Intl

7h 55m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 13

SXM3:05 pmSimpson Bay Princess Juliana

8h 43m

1 stop

ORD10:48 pmChicago O'Hare Intl

$296

Find similar

Spirit Airlines

Sep 6

ORD5:05 amChicago O'Hare Intl

7h 55m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 13

SXM3:05 pmSimpson Bay Princess Juliana

8h 43m

1 stop

ORD10:48 pmChicago O'Hare Intl

$317

Find similar

Spirit Airlines

Sep 6

ORD5:05 amChicago O'Hare Intl

7h 55m

1 stop

SXM2:00 pmSimpson Bay Princess Juliana

Sep 13

SXM3:05 pmSimpson Bay Princess Juliana

8h 43m

1 stop

ORD10:48 pmChicago O'Hare Intl

$321

Find similar

Delta flights from Chicago to St. Maarten

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

Delta

Dec 5

MDW6:00 amChicago Midway

6h 35m

1 stop

SXM2:35 pmSimpson Bay Princess Juliana

Dec 13

SXM4:00 pmSimpson Bay Princess Juliana

7h 44m

1 stop

MDW9:44 pmChicago Midway

$677

Find similar

Delta

Jan 24

MDW6:00 amChicago Midway

6h 56m

1 stop

SXM2:56 pmSimpson Bay Princess Juliana

Feb 1

SXM1:45 pmSimpson Bay Princess Juliana

10h 01m

1 stop

MDW9:46 pmChicago Midway

$767

Find similar

Delta

Dec 6

MDW6:00 amChicago Midway

6h 35m

1 stop

SXM2:35 pmSimpson Bay Princess Juliana

Dec 13

SXM4:00 pmSimpson Bay Princess Juliana

7h 44m

1 stop

MDW9:44 pmChicago Midway

$807

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$296

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 9/6

5:05 am-2:00 pm

1 stop7h 55m

Simpson Bay Princess Juliana

Sat 9/13

3:05 pm-10:48 pm

1 stop8h 43m

$317

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 9/23

10:27 am-8:12 am

2 stops20h 45m

Simpson Bay Princess Juliana

Mon 9/29

3:05 pm-10:48 pm

1 stop8h 43m

$420

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 10/16

6:07 pm-1:59 pm

2 stops18h 52m

Simpson Bay Princess Juliana

Mon 10/20

3:05 pm-6:24 pm

1 stop28h 19m

$425

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 11/4

7:00 am-4:38 pm

1 stop7h 38m

Simpson Bay Princess Juliana

Thu 11/13

5:44 pm-8:52 pm

1 stop29h 08m

$443

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Tue 11/4

7:00 am-4:38 pm

1 stop7h 38m

Simpson Bay Princess Juliana

Thu 11/13

5:44 pm-5:55 pm

2 stops26h 11m

$458

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 12/5

6:00 am-2:35 pm

1 stop6h 35m

Simpson Bay Princess Juliana

Sat 12/13

4:00 pm-9:44 pm

1 stop7h 44m

$677

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 1/24

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

Sun 2/1

1:45 pm-9:46 pm

1 stop10h 01m

$767

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/5

1:48 pm-3:21 pm

2 stops23h 33m

Simpson Bay Princess Juliana

Tue 11/11

4:20 pm-1:09 pm

2 stops22h 49m

$3,140

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 9/10

9:15 am-2:19 pm

2 stops28h 04m

Simpson Bay Princess Juliana

Sun 9/14

2:10 pm-9:36 pm

2 stops32h 26m

$3,165

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 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

Prices

Airlines

What is the cheapest month to fly to St. Maarten?

The cheapest month to fly to St. Maarten from Chicago is in August. Flight prices, which tend to average around $637, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in August, then September is your next best option. Flight prices from Chicago to St. Maarten during September average around $642.

What is the cheapest day to depart on your flight to St. Maarten?

According to our data, Tuesday is the cheapest day to fly to St. Maarten from Chicago. The lowest ticket price found for a Tuesday departure recently was $702. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. The most expensive day to fly to St. Maarten is Saturday, with ticket prices averaging around $902.

What is the cheapest time of day to depart on your flight to St. Maarten?

At noon is the cheapest time of day to fly from Chicago to St. Maarten when you can find flight prices for as low as $417. Flying to St. Maarten at noon is an ideal time because this is during off-peak travel hours. In contrast, the most expensive time of day to depart to St. Maarten is in the morning when prices are around $894.

What is the cheapest Chicago to St. Maarten flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - St. Maarten flight prices

How far in advance should I book a flight to St. Maarten?

You are more likely to see cheaper flights to St. Maarten from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $725 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to St. Maarten from Chicago for as low as $549 on momondo.

What cabin class options are available on Chicago to St. Maarten flights?

There are 2 cabin classes available to choose from on Chicago to St. Maarten flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Chicago to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to St. Maarten

Best Price Found	$139
Fastest flight time	6h 35m
Direct flights	Mon and Sun
Airports in St. Maarten	1 airport

The best one-way flight to St. Maarten from Chicago in the past 72 hours is $139. The best round-trip flight deal from Chicago to St. Maarten found on momondo in the last 72 hours is $296.

The fastest flight from Chicago to St. Maarten takes 6h 35m

Direct flights go from Chicago to St. Maarten on Monday and Sunday. Airlines offering direct flights are: United Airlines and American Airlines.

There is 1 airport near St. Maarten: Simpson Bay Princess Juliana (SXM)

Search flight deals

When did momondo last update prices for flights from Chicago to St. Maarten?
Prices for flights from Chicago to St. Maarten were last updated today.
How many operators does momondo search for flights from Chicago to St. Maarten?
As of August 2025, there are 4 operators available to choose from for flights from Chicago to St. Maarten.
How old do you have to be to fly from Chicago to St. Maarten?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago to St. Maarten.
What documentation or ID do you need to fly to St. Maarten?
The travel and health documents required for your trip to St. Maarten can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at St. Maarten. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Chicago to St. Maarten?
Based on momondo bookings for flights between Chicago and St. Maarten, the leading plane model is Boeing 737-700, making up 45.56% of the total bookings. Other popular models include Airbus A319 with 38.89% and Boeing 737 MAX 8 with 15.56%.

Best airlines flying from Chicago to St. Maarten

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

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $333	Free Cancellation	Rating 6.3 8,038 reviews	Search Spirit Airlines flights
Delta	PriceFrom $564	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
American Airlines	PriceFrom $614	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $654	Free Cancellation	Rating 7.4 8,925 reviews	Search United Airlines 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?

momondo does allow users to show only those flights to St. Maarten from Chicago which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Chicago to St. Maarten?

momondo helps you find the best flight between Chicago and St. Maarten by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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.

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Find better results for your trip to St. Maarten

Popular cities in St. Maarten

Flights to Simpson Bayfrom $234

Cheap flights from Chicago to St. Maarten from $139

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 to St. Maarten departing on 9/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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 to St. Maarten

Cheap round-trip flights

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Spirit Airlines flights from Chicago to St. Maarten

Our best Spirit Airlines deals on Chicago to St. Maarten flight tickets

Delta flights from Chicago to St. Maarten

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

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See travel insights to St. Maarten from

How to get the cheapest flight ticket from Chicago 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 month to fly to St. Maarten?

What is the cheapest day to depart on your flight to St. Maarten?

What is the cheapest time of day to depart on your flight to St. Maarten?

What is the cheapest Chicago to St. Maarten flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago - St. Maarten flight prices

How far in advance should I book a flight to St. Maarten?

What cabin class options are available on Chicago to St. Maarten flights?

There are 2 cabin classes available to choose from on Chicago to St. Maarten flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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

Spirit Airlines, Copa Airlines, and Delta are the most popular carriers operating from Chicago to St. Maarten

What airlines fly to St. Maarten?

Cheap Chicago to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to St. Maarten

Best Price Found

Fastest flight time

Direct flights

Airports in St. Maarten

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

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

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

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

What is the most popular plane model from Chicago to St. Maarten?

Best airlines flying from Chicago to St. Maarten

Compare and see reviews for airlines that fly from Chicago 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