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 53% of people opting to fly with this airline when traveling to St. Maarten. Keep in mind that there are 5 different airlines that fly to St. Maarten on a routine basis, so you have a few additional options to choose from.

Which airline has the best punctuality record on Chicago to St. Maarten flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 33% of their flights experiencing any sort of delay.

What is the most punctual flight time for Chicago to St. Maarten flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Sunday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

How often are flights from Chicago to St. Maarten delayed?

Historically, on average around 34% of flights between Chicago and St. Maarten have experienced a delay on any given week. The average delay length over the past 12 months has been 129 minutes.

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

Spirit Airlines is the most popular carrier 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 December 2025, there are 5 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.

$77 Cheap Flights from Chicago to St. Maarten in 2025/26

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:43 pm - 2:10 pm

ORD

SXM

15h 27m1 stop

3:15 pm - 11:46 pm

SXM

ORD

10h 31m1 stop

$230Spirit Airlines

Thu, Jan 8 - Thu, Jan 15

8:43 pm - 2:10 pm

ORD

SXM

15h 27m1 stop

3:15 pm - 10:03 pm

SXM

ORD

8h 48m1 stop

$231Spirit Airlines

Fri, Jan 23 - Sat, Jan 31

5:15 am - 2:10 pm

ORD

SXM

6h 55m1 stop

3:15 pm - 12:18 am

SXM

ORD

11h 03m1 stop

$238Spirit Airlines

Mon, Feb 9 - Wed, Feb 18

8:43 pm - 2:10 pm

ORD

SXM

15h 27m1 stop

3:15 pm - 11:46 pm

SXM

ORD

10h 31m1 stop

$239Spirit Airlines

Thu, Jan 29 - Mon, Feb 2

5:00 am - 2:15 pm

ORD

SXM

7h 15m1 stop

3:15 pm - 11:46 pm

SXM

ORD

10h 31m1 stop

$251Spirit Airlines

Sat, Jan 3 - Fri, Jan 9

6:00 am - 3:20 pm

MDW

SXM

7h 20m1 stop

4:30 pm - 11:25 pm

SXM

MDW

8h 55m1 stop

$287Frontier

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

$308Frontier

Sat, Feb 14 - Sat, Feb 28

6:00 am - 2:55 pm

MDW

SXM

6h 55m1 stop

1:55 pm - 10:22 pm

SXM

MDW

10h 27m1 stop

$501Delta

Sun, Feb 1 - Fri, Feb 6

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

5:10 pm - 2:10 pm

MDW

SXM

19h 00m2 stops

4:20 pm - 10:10 am

SXM

MDW

19h 50m1 stop

$553Multiple Airlines

Wed, Jan 7 - Wed, Jan 14

Spirit Airlines flights from Chicago to St. Maarten

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

Spirit Airlines

Jan 8

ORD8:43 pmChicago O'Hare Intl

15h 27m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Jan 15

SXM3:15 pmSimpson Bay Princess Juliana

10h 31m

1 stop

ORD11:46 pmChicago O'Hare Intl

$230

Find similar

Spirit Airlines

Jan 23

ORD8:43 pmChicago O'Hare Intl

15h 27m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Jan 31

SXM3:15 pmSimpson Bay Princess Juliana

8h 48m

1 stop

ORD10:03 pmChicago O'Hare Intl

$231

Find similar

Spirit Airlines

Feb 9

ORD5:15 amChicago O'Hare Intl

6h 55m

1 stop

SXM2:10 pmSimpson Bay Princess Juliana

Feb 18

SXM3:15 pmSimpson Bay Princess Juliana

11h 03m

1 stop

ORD12:18 amChicago O'Hare Intl

$238

Find similar

Frontier flights from Chicago to St. Maarten

Our best Frontier deals on Chicago 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

$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

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/8

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Thu 1/15

3:15 pm-11:46 pm

1 stop10h 31m

$230

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/23

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Sat 1/31

3:15 pm-10:03 pm

1 stop8h 48m

$231

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:10 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Wed 2/18

3:15 pm-12:18 am

1 stop11h 03m

$238

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Thu 1/29

8:43 pm-2:10 pm

1 stop15h 27m

Simpson Bay Princess Juliana

Mon 2/2

3:15 pm-11:46 pm

1 stop10h 31m

$239

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 1/3

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Fri 1/9

3:15 pm-11:46 pm

1 stop10h 31m

$251

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

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

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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

Delays

Other information

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 $585, 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 $612.

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 $881.

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 $827.

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 $685 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 $507 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.

Can stopping save me money on Chicago to St. Maarten flights?

You could potentially save up to 25% on your flight if you consider stops on a Chicago to St. Maarten flight.

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	$313
Fastest flight time	5h 12m
Direct flights	Mon and Sun
Airports in St. Maarten	2 airports

The best one-way flight to St. Maarten from Chicago in the past 72 hours is $313. The best round-trip flight deal from Chicago to St. Maarten found on momondo in the last 72 hours is $556.

The fastest flight from Chicago to St. Maarten takes 5h 12m

Direct flights go from Chicago to St. Maarten on Monday and Sunday. The only airline offering direct flights is United Airlines.

There are 2 airports in St. Maarten. From Chicago there are direct flights to 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 December 2025, there are 5 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 MAX 8, making up 54.47% of the total bookings. Other popular models include Airbus A319 with 26.83%, Boeing 737-700 with 9.76%, and Airbus A320-100/200 with 4.07%.

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
Delta	PriceFrom $292	Free Cancellation	Rating 7.9 8,008 reviews	Search Delta flights
Spirit Airlines	PriceFrom $315	Free Cancellation	Rating 6.3 8,179 reviews	Search Spirit Airlines flights
United Airlines	PriceFrom $410	Free Cancellation	Rating 7.4 9,095 reviews	Search United Airlines flights
JetBlue	PriceFrom $535	Free Cancellation	Rating 7.2 2,899 reviews	Search JetBlue flights
American Airlines	PriceFrom $540	Free Cancellation	Rating 7.2 11,050 reviews	Search American 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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Popular cities in St. Maarten

Flights to Simpson Bayfrom $174

Cheap flights from Chicago to St. Maarten from $77

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 2/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Filter for what you want

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Find the cheapest flights from Chicago to St. Maarten

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Spirit Airlines flights from Chicago to St. Maarten

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

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Our best Frontier 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

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.

Can stopping save me money on Chicago to St. Maarten flights?

You could potentially save up to 25% on your flight if you consider stops on a Chicago to St. Maarten flight.

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

Spirit Airlines is the most popular carrier operating from Chicago to St. Maarten

What airlines fly to St. Maarten?

How often are flights from Chicago to St. Maarten delayed?

Historically, on average around 34% of flights between Chicago and St. Maarten have experienced a delay on any given week. The average delay length over the past 12 months has been 129 minutes.

What is the most punctual flight time for Chicago to St. Maarten flights?

Generally, flights departing in the morning tend to experience fewer delays. Flights in the morning have, in the past, seen delays more frequently in comparison.

What day of the week experiences the fewest flight delays on this route?

Sunday is statistically the day of the week which experiences the fewest number of delays on this flight route. Saturday has historically seen more delays on average compared to the rest of the week.

Which airline has the best punctuality record on Chicago to St. Maarten flights?

According to our data, United Airlines have had the least number of delays on this route over the last 12 months; with about 33% of their flights experiencing any sort of delay.

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