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Cheap flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to St. Maarten departing on 9/22. 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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Find the cheapest flights from Chicago O'Hare Intl Airport to St. Maarten

Cheap round-trip flights

Spirit Airlines Logo
5:05 am - 1:59 pmORD-SXM
7h 54m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$337Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Oct 25
Spirit Airlines Logo
5:05 am - 1:59 pmORD-SXM
7h 54m1 stop
Spirit Airlines Logo
3:05 pm - 1:03 amSXM-ORD
10h 58m1 stop
$341Spirit Airlines
Find Deal
Sat, Oct 18 - Sat, Nov 1
Spirit Airlines Logo
5:05 am - 1:59 pmORD-SXM
7h 54m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$342Spirit Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Spirit Airlines Logo
5:05 am - 1:59 pmORD-SXM
7h 54m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$351Spirit Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Spirit Airlines Logo
5:05 am - 1:59 pmORD-SXM
7h 54m1 stop
Spirit Airlines Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$356Spirit Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
Spirit Airlines Logo
7:41 pm - 1:59 pmORD-SXM
17h 18m1 stop
Spirit Airlines Logo
3:05 pm - 1:03 amSXM-ORD
10h 58m1 stop
$357Spirit Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
Spirit Airlines Logo
5:05 am - 3:10 pmORD-SXM
8h 05m1 stop
Spirit Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$385Spirit Airlines
Find Deal
Mon, Feb 9 - Wed, Feb 18
Spirit Airlines Logo
5:59 pm - 3:10 pmORD-SXM
19h 11m1 stop
Spirit Airlines Logo
4:28 pm - 11:42 pmSXM-ORD
9h 14m1 stop
$389Spirit Airlines
Find Deal
Sun, Dec 7 - Fri, Dec 12
Logo
5:50 pm - 1:59 pmORD-SXM
19h 09m2 stops
Logo
3:05 pm - 6:36 pmSXM-ORD
28h 31m1 stop
$405
Find Deal
Fri, Oct 24 - Mon, Oct 27
Logo
6:40 pm - 7:30 pmORD-SXM
23h 50m3 stops
Logo
3:05 pm - 11:45 pmSXM-ORD
9h 40m1 stop
$417
Find Deal
Sat, Oct 11 - Sat, Oct 18

Spirit Airlines flights from Chicago O'Hare Intl Airport to St. Maarten

Our best Spirit Airlines deals on Chicago O'Hare Intl Airport to St. Maarten flight tickets
Spirit Airlines
Oct 18
ORD5:05 amChicago O'Hare Intl
7h 54m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Oct 25
SXM3:05 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:45 pmChicago O'Hare Intl
$337
Find similar
Spirit Airlines
Oct 18
ORD5:05 amChicago O'Hare Intl
7h 54m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Nov 1
SXM3:05 pmSimpson Bay Princess Juliana
10h 58m
1 stop
ORD1:03 amChicago O'Hare Intl
$341
Find similar
Spirit Airlines
Oct 11
ORD5:05 amChicago O'Hare Intl
7h 54m
1 stop
SXM1:59 pmSimpson Bay Princess Juliana
Oct 18
SXM3:05 pmSimpson Bay Princess Juliana
9h 40m
1 stop
ORD11:45 pmChicago O'Hare Intl
$342
Find similar

American Airlines flights from Chicago O'Hare Intl Airport to St. Maarten

Our best American Airlines deals on Chicago O'Hare Intl Airport to St. Maarten flight tickets
American Airlines
Sep 10
ORD5:00 amChicago O'Hare Intl
7h 19m
1 stop
SXM1:19 pmSimpson Bay Princess Juliana
Sep 23
SXM2:20 pmSimpson Bay Princess Juliana
9h 06m
1 stop
ORD10:26 pmChicago O'Hare Intl
$677
Find similar
American Airlines
Sep 10
ORD5:00 amChicago O'Hare Intl
7h 19m
1 stop
SXM1:19 pmSimpson Bay Princess Juliana
Sep 23
SXM2:20 pmSimpson Bay Princess Juliana
10h 28m
2 stops
ORD11:48 pmChicago O'Hare Intl
$682
Find similar
American Airlines
Sep 10
ORD8:29 pmChicago O'Hare Intl
15h 50m
2 stops
SXM1:19 pmSimpson Bay Princess Juliana
Sep 23
SXM2:20 pmSimpson Bay Princess Juliana
18h 00m
2 stops
ORD7:20 amChicago O'Hare Intl
$747
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport to St. Maarten that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated August 27, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to St. Maarten that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/25

3:05 pm-11:45 pm

1 stop9h 40m

$337

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/18

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 11/1

3:05 pm-1:03 am

1 stop10h 58m

$341

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$342

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$351

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

5:05 am-1:59 pm

1 stop7h 54m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$356

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/24

7:41 pm-1:59 pm

1 stop17h 18m

Simpson Bay Princess Juliana

Mon 10/27

3:05 pm-1:03 am

1 stop10h 58m

$357

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

5:05 am-3:10 pm

1 stop8h 05m

Simpson Bay Princess Juliana

Wed 2/18

4:28 pm-11:42 pm

1 stop9h 14m

$385

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sun 12/7

5:59 pm-3:10 pm

1 stop19h 11m

Simpson Bay Princess Juliana

Fri 12/12

4:28 pm-11:42 pm

1 stop9h 14m

$389

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 10/24

5:50 pm-1:59 pm

2 stops19h 09m

Simpson Bay Princess Juliana

Mon 10/27

3:05 pm-6:36 pm

1 stop28h 31m

$405

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Sat 10/11

6:40 pm-7:30 pm

3 stops23h 50m

Simpson Bay Princess Juliana

Sat 10/18

3:05 pm-11:45 pm

1 stop9h 40m

$417

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to St. Maarten from

How to get the cheapest flight ticket from Chicago O'Hare Intl 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 month to fly to St. Maarten?

The cheapest month to fly to St. Maarten from Chicago O'Hare Intl Airport is in September. Flight prices, which tend to average around $489, are often lower during this time because this is during the off-season. If you’re not able to fly to St. Maarten in September, then August is your next best option. Flight prices from Chicago O'Hare Intl Airport to St. Maarten during August average around $585.

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 O'Hare Intl Airport. 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 $903.

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 O'Hare Intl Airport 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 $886.

What is the cheapest Chicago O'Hare Intl to St. Maarten flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Chicago O'Hare Intl - 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 O'Hare Intl Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $702 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 O'Hare Intl Airport for as low as $549 on momondo.

What cabin class options are available on Chicago O'Hare Intl to St. Maarten flights?

There are 2 cabin classes available to choose from on Chicago O'Hare Intl 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 O'Hare Intl Airport to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to St. Maarten

Best Price Found

$368

Fastest flight time

4h 45m

Direct flights

Mon and Sun

Airports in St. Maarten

1 airport
The best one-way flight to St. Maarten from Chicago O'Hare Intl Airport in the past 72 hours is $368. The best round-trip flight deal from Chicago O'Hare Intl Airport to St. Maarten found on momondo in the last 72 hours is $797.
The fastest flight from Chicago O'Hare Intl Airport to St. Maarten takes 4h 45m
Direct flights go from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to St. Maarten?

    Prices for flights from Chicago O'Hare Intl Airport to St. Maarten are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to St. Maarten?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to St. Maarten?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to St. Maarten?

Best airlines flying from Chicago O'Hare Intl Airport to St. Maarten

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to St. Maarten with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $316Free CancellationRating
6.3
8,030 reviews
Search Spirit Airlines flights
DeltaPriceFrom $564Free CancellationRating
7.9
7,977 reviews
Search Delta flights
American AirlinesPriceFrom $618Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $654Free CancellationRating
7.4
8,945 reviews
Search United Airlines flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to St. Maarten. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Chicago to St. Maarten flights to just show those with flexible booking policies.

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?

Yes. momondo can track prices for Chicago to St. Maarten flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Popular flights according to clicks in the last 7 days on momondo
Flights to Simpson Bayfrom $257