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Cheap flights from Chicago to St. Maarten from $134

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 1/6. 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 to St. Maarten

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to St. Maarten that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to St. Maarten.

Cheap last minute flights

Planning a quick getaway from Chicago to St. Maarten? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to St. Maarten, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to St. Maarten

Find recent round-trip train or bus tickets from Chicago to St. Maarten.

All round-trip flight deals to St. Maarten

The cheapest plane tickets to St. Maarten found on KAYAK recently.
5:43 pm - 11:20 amORD-SXM
15h 37m2 stops
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Mon, Jan 13 - Sat, Jan 18
7:45 pm - 5:19 pmORD-SXM
19h 34m2 stops
6:29 pm - 8:13 pmSXM-ORD
27h 44m1 stop
Fri, Dec 13 - Fri, Dec 20
10:02 pm - 5:19 pmORD-SXM
17h 17m2 stops
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Fri, Jan 17 - Sat, Jan 25
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 11:02 pmSXM-ORD
9h 37m1 stop
$402Spirit Airlines
Find Deal
Sat, Jan 4 - Fri, Jan 10
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 11:02 pmSXM-ORD
9h 37m1 stop
$404Spirit Airlines
Find Deal
Sat, Jan 4 - Fri, Jan 10
6:00 am - 3:11 pmMDW-SXM
7h 11m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$630Delta
Find Deal
Wed, Jan 1 - Thu, Jan 9
5:02 am - 4:09 pmORD-SXM
9h 07m2 stops
5:19 pm - 8:30 amSXM-ORD
17h 11m2 stops
$634American Airlines
Find Deal
Tue, Dec 31 - Tue, Jan 21
5:02 am - 4:09 pmORD-SXM
9h 07m2 stops
4:18 pm - 7:24 amSXM-ORD
17h 06m2 stops
$645American Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
6:00 am - 4:20 pmMDW-SXM
8h 20m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$655Delta
Find Deal
Sat, Jan 4 - Fri, Jan 10
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$665United Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
1:00 pm - 11:20 amORD-SXM
20h 20m1 stop
Mon, Jan 6
1:00 pm - 11:20 amORD-SXM
20h 20m1 stop
Wed, Jan 8
4:41 pm - 11:20 amORD-SXM
16h 39m2 stops
Mon, Jan 6
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
$183Spirit Airlines
Find Deal
Wed, Dec 4
5:11 pm - 2:30 pmORD-SXM
19h 19m1 stop
$185Spirit Airlines
Find Deal
Tue, Jan 7
5:22 am - 3:02 pmORD-SXM
8h 40m2 stops
$312American Airlines
Find Deal
Wed, Mar 12
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
$312Delta
Find Deal
Tue, Jan 7
6:00 am - 3:11 pmMDW-SXM
7h 11m1 stop
$334Delta
Find Deal
Sat, Jan 4
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$378United Airlines
Find Deal
Sat, Jan 4
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$468United Airlines
Find Deal
Sat, Dec 7
6:10 pm - 5:19 pmORD-SXM
21h 09m1 stop
3:25 pm - 9:20 amSXM-ORD
19h 55m1 stop
Fri, Nov 22 - Mon, Nov 25
6:10 pm - 5:19 pmORD-SXM
21h 09m1 stop
11:55 am - 9:04 amSXM-ORD
23h 09m1 stop
Fri, Nov 22 - Tue, Nov 26
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 9:20 amSXM-ORD
19h 55m1 stop
$891Spirit Airlines
Find Deal
Mon, Nov 25 - Sat, Nov 30
8:25 pm - 2:19 pmORD-SXM
15h 54m1 stop
4:25 pm - 11:55 pmSXM-ORD
9h 30m1 stop
$1,045American Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
8:28 pm - 2:19 pmORD-SXM
15h 51m2 stops
3:20 pm - 11:55 pmSXM-ORD
10h 35m1 stop
$1,049American Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 9:20 amSXM-ORD
19h 55m1 stop
$1,146Spirit Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
4:55 pm - 7:34 amSXM-ORD
16h 39m1 stop
$1,200United Airlines
Find Deal
Sat, Nov 23 - Tue, Nov 26
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
4:00 pm - 9:46 pmSXM-MDW
7h 46m1 stop
$1,248Delta
Find Deal
Fri, Nov 22 - Tue, Nov 26
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:51 pm - 6:45 pmSXM-ORD
5h 54mnonstop
$1,270United Airlines
Find Deal
Sat, Nov 23 - Sat, Nov 30
6:00 am - 2:35 pmMDW-SXM
6h 35m1 stop
4:00 pm - 9:46 pmSXM-MDW
7h 46m1 stop
$1,273Delta
Find Deal
Fri, Nov 22 - Mon, Nov 25
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$665United Airlines
Find Deal
Sat, Feb 8 - Sat, Feb 15
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$729Lufthansa
Find Deal
Sun, Jan 5 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$730United Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$755United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 18
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$805United Airlines
Find Deal
Sun, Jan 12 - Sat, Jan 18
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$838United Airlines
Find Deal
Sat, Jan 4 - Sun, Jan 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$850United Airlines
Find Deal
Sun, Mar 2 - Sat, Mar 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$933United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 25
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$1,010United Airlines
Find Deal
Sat, Jan 25 - Sat, Feb 1
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
1:16 pm - 6:10 pmSXM-ORD
5h 54mnonstop
$1,121United Airlines
Find Deal
Sat, Mar 8 - Sat, Mar 22

Spirit Airlines flights from Chicago to St. Maarten

Our best Spirit Airlines deals on Chicago to St. Maarten flight tickets
Spirit Airlines
Jan 4
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 10
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl
Spirit Airlines
Jan 4
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 10
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl
Spirit Airlines
Jan 8
ORD5:00 amChicago O'Hare Intl
7h 30m
1 stop
SXM2:30 pmSimpson Bay Princess Juliana
Jan 15
SXM3:25 pmSimpson Bay Princess Juliana
9h 37m
1 stop
ORD11:02 pmChicago O'Hare Intl

Air Canada flights from Chicago to St. Maarten

Our best Air Canada deals on Chicago to St. Maarten flight tickets
Air Canada
Dec 7
ORD6:38 pmChicago O'Hare Intl
19h 17m
2 stops
SXM3:55 pmSimpson Bay Princess Juliana
Dec 14
SXM5:45 pmSimpson Bay Princess Juliana
16h 11m
2 stops
ORD7:56 amChicago O'Hare Intl
Air Canada
Dec 7
ORD8:25 pmChicago O'Hare Intl
17h 30m
2 stops
SXM3:55 pmSimpson Bay Princess Juliana
Dec 14
SXM5:45 pmSimpson Bay Princess Juliana
16h 11m
2 stops
ORD7:56 amChicago O'Hare Intl
Air Canada
Jan 5
ORD8:30 pmChicago O'Hare Intl
17h 45m
1 stop
SXM4:15 pmSimpson Bay Princess Juliana
Jan 12
SXM4:55 pmSimpson Bay Princess Juliana
23h 50m
1 stop
ORD2:45 pmChicago O'Hare Intl

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 day to depart on your flight to St. Maarten?

According to our data, Monday is the cheapest day to fly to St. Maarten from Chicago. The lowest ticket price found for a Monday departure recently was $604. 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 $833.

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

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

There are 3 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 70% 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

$134

Fastest flight time

5h 06m

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 $134. The best round-trip flight deal from Chicago to St. Maarten found on momondo in the last 72 hours is $355.
The fastest flight from Chicago to St. Maarten takes 5h 06m
Direct flights go from Chicago to St. Maarten on Monday and Sunday. Airlines offering direct flights are: United Airlines and Lufthansa.
There is 1 airport near St. Maarten: Simpson Bay Princess Juliana (SXM)

  • 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?

  • 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?


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 AirlinesPriceFrom $263Free CancellationRating
6.3
8,169 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $553Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $554Free CancellationRating
8.0
8,755 reviews
Search Delta flights
United AirlinesPriceFrom $617Free CancellationRating
7.4
9,172 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.


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