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

Spirit Airlines, JetBlue, and Air Canada are the most popular carriers operating from Chicago to St. Maarten

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.

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 October 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.

$133 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.

5:05 am - 3:10 pmORD-SXM

8h 05m1 stop

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$343Spirit Airlines

Find Deal

mié., ene. 28 - vie., feb. 6

5:05 am - 3:10 pmORD-SXM

8h 05m1 stop

4:28 pm - 11:42 pmSXM-ORD

9h 14m1 stop

$361Spirit Airlines

Find Deal

sáb., ene. 31 - sáb., feb. 7

5:00 am - 4:22 pmORD-SXM

9h 22m1 stop

5:24 pm - 12:37 amSXM-ORD

9h 13m1 stop

$375American Airlines

Find Deal

mar., nov. 18 - mar., nov. 25

7:07 pm - 2:19 pmORD-SXM

17h 12m1 stop

5:24 pm - 12:37 amSXM-ORD

9h 13m1 stop

$377American Airlines

Find Deal

sáb., nov. 8 - mié., nov. 12

4:01 pm - 2:10 pmORD-SXM

44h 09m2 stops

3:15 pm - 1:57 pmSXM-ORD

24h 42m1 stop

$393Multiple Airlines

Find Deal

mié., dic. 3 - mié., dic. 10

8:45 am - 2:15 pmORD-SXM

27h 30m1 stop

3:20 pm - 11:37 amSXM-ORD

22h 17m2 stops

$399Multiple Airlines

Find Deal

jue., nov. 27 - lun., dic. 1

6:00 am - 2:55 pmMDW-SXM

6h 55m1 stop

4:20 pm - 11:40 pmSXM-MDW

9h 20m1 stop

$433Delta

Find Deal

dom., nov. 9 - mié., nov. 12

6:45 am - 4:38 pmORD-SXM

7h 53m1 stop

3:22 pm - 10:21 pmSXM-ORD

8h 59m1 stop

$453JetBlue

Find Deal

lun., nov. 17 - sáb., nov. 22

6:45 am - 4:38 pmORD-SXM

7h 53m1 stop

2:28 pm - 10:21 pmSXM-ORD

9h 53m1 stop

$459JetBlue

Find Deal

mié., nov. 19 - sáb., nov. 22

6:00 am - 2:56 pmMDW-SXM

6h 56m1 stop

1:45 pm - 9:46 pmSXM-MDW

10h 01m1 stop

$587Delta

Find Deal

mié., ene. 28 - vie., feb. 6

Spirit Airlines flights from Chicago to St. Maarten

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

Spirit Airlines

Jan 28

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 6

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$343

Find similar

Spirit Airlines

Jan 31

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 7

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$361

Find similar

Spirit Airlines

Feb 9

ORD5:05 amChicago O'Hare Intl

8h 05m

1 stop

SXM3:10 pmSimpson Bay Princess Juliana

Feb 18

SXM4:28 pmSimpson Bay Princess Juliana

9h 14m

1 stop

ORD11:42 pmChicago O'Hare Intl

$385

Find similar

American Airlines flights from Chicago to St. Maarten

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

American Airlines

Nov 18

ORD5:00 amChicago O'Hare Intl

9h 22m

1 stop

SXM4:22 pmSimpson Bay Princess Juliana

Nov 25

SXM5:24 pmSimpson Bay Princess Juliana

9h 13m

1 stop

ORD12:37 amChicago O'Hare Intl

$375

Find similar

American Airlines

Nov 8

ORD7:07 pmChicago O'Hare Intl

17h 12m

1 stop

SXM2:19 pmSimpson Bay Princess Juliana

Nov 12

SXM5:24 pmSimpson Bay Princess Juliana

9h 13m

1 stop

ORD12:37 amChicago O'Hare Intl

$377

Find similar

American Airlines

Dec 4

ORD6:35 pmChicago O'Hare Intl

17h 17m

1 stop

SXM1:52 pmSimpson Bay Princess Juliana

Dec 11

SXM5:25 pmSimpson Bay Princess Juliana

20h 41m

1 stop

ORD12:06 pmChicago O'Hare Intl

$378

Find similar

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mié. 1/28

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

vie. 2/6

4:28 pm-11:42 pm

1 stop9h 14m

$343

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 1/31

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

sáb. 2/7

4:28 pm-11:42 pm

1 stop9h 14m

$361

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mar. 11/18

5:00 am-4:22 pm

1 stop9h 22m

Simpson Bay Princess Juliana

mar. 11/25

5:24 pm-12:37 am

1 stop9h 13m

$375

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

sáb. 11/8

7:07 pm-2:19 pm

1 stop17h 12m

Simpson Bay Princess Juliana

mié. 11/12

5:24 pm-12:37 am

1 stop9h 13m

$377

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mié. 12/3

4:01 pm-2:10 pm

2 stops44h 09m

Simpson Bay Princess Juliana

mié. 12/10

3:15 pm-1:57 pm

1 stop24h 42m

$393

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

jue. 11/27

8:45 am-2:15 pm

1 stop27h 30m

Simpson Bay Princess Juliana

lun. 12/1

3:20 pm-11:37 am

2 stops22h 17m

$399

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

dom. 11/9

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

mié. 11/12

4:20 pm-11:40 pm

1 stop9h 20m

$433

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

lun. 11/17

6:45 am-4:38 pm

1 stop7h 53m

Simpson Bay Princess Juliana

sáb. 11/22

3:22 pm-10:21 pm

1 stop8h 59m

$453

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

mié. 11/19

6:45 am-4:38 pm

1 stop7h 53m

Simpson Bay Princess Juliana

sáb. 11/22

2:28 pm-10:21 pm

1 stop9h 53m

$459

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

mié. 1/28

6:00 am-2:56 pm

1 stop6h 56m

Simpson Bay Princess Juliana

vie. 2/6

1:45 pm-9:46 pm

1 stop10h 01m

$587

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 $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 $910.

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 $884.

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 $700 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 $522 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 5% 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	$553
Fastest flight time	4h 45m
Direct flights	Mon and Sun
Airports in St. Maarten	1 airport

The best flight deal from Chicago to St. Maarten found on momondo in the last 72 hours is $553

The fastest flight from Chicago to St. Maarten takes 4h 45m

Direct flights go from Chicago to St. Maarten on Monday and Sunday. There are no airlines offering direct flights.

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 October 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 MAX 8, making up 39.33% of the total bookings. Other popular models include Airbus A319 with 34.83% and Boeing 737-700 with 25.84%.

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 $316	Free Cancellation	Rating 6.3 8,095 reviews	Search Spirit Airlines flights
Delta	PriceFrom $329	Free Cancellation	Rating 7.9 7,978 reviews	Search Delta flights
United Airlines	PriceFrom $597	Free Cancellation	Rating 7.4 8,991 reviews	Search United Airlines flights
American Airlines	PriceFrom $610	Free Cancellation	Rating 7.2 11,024 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.

Start using Trips

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Popular cities in St. Maarten

Flights to Simpson Bayfrom $220

Cheap flights from Chicago to St. Maarten from $133

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 12/17. 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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Trusted and free

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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

American Airlines flights from Chicago to St. Maarten

Our best American Airlines 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.

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

You could potentially save up to 5% 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, JetBlue, and Air Canada 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