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Cheap flights from Chicago to St. Maarten from $127

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 2/7. 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.
1:44 pm - 5:18 pmORD-SXM
25h 34m1 stop
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Fri, Jan 10 - Sat, Jan 18
10:02 pm - 5:19 pmORD-SXM
17h 17m2 stops
6:29 pm - 12:51 amSXM-ORD
8h 22m1 stop
Fri, Jan 24 - Sat, Feb 1
5:11 am - 2:30 pmORD-SXM
7h 19m1 stop
3:25 pm - 11:32 pmSXM-ORD
10h 07m1 stop
$384Spirit Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:11 am - 2:30 pmORD-SXM
7h 19m1 stop
3:25 pm - 11:32 pmSXM-ORD
10h 07m1 stop
$390Spirit Airlines
Find Deal
Sat, Feb 1 - Wed, Feb 5
7:25 pm - 11:07 amORD-SXM
14h 42m1 stop
12:15 pm - 11:39 pmSXM-ORD
12h 24m1 stop
$534JetBlue
Find Deal
Sat, Jun 7 - Sat, Jun 14
7:25 pm - 11:07 amORD-SXM
14h 42m1 stop
12:15 pm - 11:39 pmSXM-ORD
12h 24m1 stop
$538JetBlue
Find Deal
Sat, May 31 - Sat, Jun 14
5:00 am - 1:10 pmORD-SXM
7h 10m1 stop
2:26 pm - 9:24 pmSXM-ORD
7h 58m1 stop
$630American Airlines
Find Deal
Wed, Mar 26 - Wed, Apr 2
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
1:40 pm - 10:20 pmSXM-MDW
10h 40m1 stop
$630Delta
Find Deal
Wed, Jan 22 - Wed, Jan 29
5:10 am - 4:11 pmORD-SXM
9h 01m2 stops
5:19 pm - 8:30 amSXM-ORD
17h 11m2 stops
$634American Airlines
Find Deal
Wed, Jan 22 - Wed, Jan 29
6:00 am - 2:01 pmMDW-SXM
7h 01m1 stop
1:40 pm - 10:24 pmSXM-MDW
9h 44m1 stop
$713Delta
Find Deal
Sun, Mar 23 - Thu, Apr 3
10:02 pm - 5:19 pmORD-SXM
17h 17m2 stops
$127Frontier
Find Deal
Fri, Feb 7
5:11 am - 2:30 pmORD-SXM
7h 19m1 stop
$153Spirit Airlines
Find Deal
Sat, Feb 8
5:28 pm - 11:20 amORD-SXM
15h 52m2 stops
Mon, Feb 10
1:44 pm - 11:20 amORD-SXM
19h 36m1 stop
Mon, Feb 10
3:56 pm - 2:30 pmORD-SXM
20h 34m1 stop
$196Spirit Airlines
Find Deal
Thu, Feb 6
6:00 am - 3:16 pmMDW-SXM
7h 16m1 stop
$312Delta
Find Deal
Sun, Feb 9
5:45 am - 3:16 pmORD-SXM
7h 31m1 stop
$312Delta
Find Deal
Tue, Feb 11
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$333United Airlines
Find Deal
Sat, Feb 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
$353United Airlines
Find Deal
Sun, Feb 9
8:25 pm - 4:15 pmORD-SXM
17h 50m1 stop
$382Air Canada
Find Deal
Sun, Dec 29
2:19 pm - 5:19 pmORD-SXM
25h 00m2 stops
3:25 pm - 11:04 amSXM-ORD
21h 39m1 stop
Thu, Dec 26 - Mon, Dec 30
2:19 pm - 5:19 pmORD-SXM
25h 00m2 stops
11:55 am - 8:40 pmSXM-ORD
10h 45m1 stop
Thu, Dec 26 - Sun, Dec 29
5:11 pm - 2:30 pmORD-SXM
19h 19m1 stop
3:25 pm - 4:06 pmSXM-ORD
26h 41m1 stop
$846Spirit Airlines
Find Deal
Fri, Dec 27 - Mon, Dec 30
5:00 am - 2:30 pmORD-SXM
7h 30m1 stop
3:25 pm - 7:51 pmSXM-ORD
30h 26m1 stop
$914Spirit Airlines
Find Deal
Mon, Dec 23 - Mon, Dec 30
6:55 pm - 12:30 pmORD-SXM
15h 35m1 stop
1:30 pm - 12:26 amSXM-ORD
12h 56m1 stop
$1,035American Airlines
Find Deal
Mon, Dec 23 - Tue, Dec 31
6:39 pm - 12:30 pmORD-SXM
15h 51m2 stops
1:30 pm - 12:26 amSXM-ORD
12h 56m1 stop
$1,039American Airlines
Find Deal
Mon, Dec 23 - Tue, Dec 31
5:40 am - 3:11 pmORD-SXM
7h 31m1 stop
1:50 pm - 11:56 pmSXM-ORD
12h 06m1 stop
$1,130Delta
Find Deal
Tue, Dec 24 - Tue, Dec 31
5:40 am - 3:11 pmORD-SXM
7h 31m1 stop
1:50 pm - 9:20 pmSXM-ORD
9h 30m1 stop
$1,165Delta
Find Deal
Tue, Dec 24 - Sun, Dec 29
9:05 pm - 1:51 pmORD-SXM
14h 46m1 stop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$2,110United Airlines
Find Deal
Mon, Dec 23 - Sun, Dec 29
6:00 am - 3:51 pmORD-SXM
7h 51m1 stop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$2,852United Airlines
Find Deal
Wed, Dec 25 - Sun, Jan 5
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$722Lufthansa
Find Deal
Sun, Jan 19 - Sun, Jan 26
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$732United Airlines
Find Deal
Sun, Jan 19 - Sun, Jan 26
8:45 am - 2:52 pmORD-SXM
5h 07mnonstop
1:16 pm - 6:10 pmSXM-ORD
5h 54mnonstop
$813United Airlines
Find Deal
Sun, Mar 9 - Sun, Mar 16
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$838United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
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
$883United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$920United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$925United Airlines
Find Deal
Sat, Jan 11 - Sat, Jan 25
10:37 am - 4:49 pmORD-SXM
5h 12mnonstop
1:25 pm - 6:08 pmSXM-ORD
5h 43mnonstop
$933United Airlines
Find Deal
Sat, Apr 5 - Sat, Apr 12
8:45 am - 3:52 pmORD-SXM
5h 07mnonstop
2:46 pm - 6:40 pmSXM-ORD
5h 54mnonstop
$995United Airlines
Find Deal
Sun, Jan 5 - Sun, Jan 12

Frontier flights from Chicago to St. Maarten

Our best Frontier deals on Chicago to St. Maarten flight tickets
Frontier
Mar 23
MDW5:45 pmChicago Midway
22h 30m
2 stops
SXM5:15 pmSimpson Bay Princess Juliana
Mar 31
SXM6:35 pmSimpson Bay Princess Juliana
19h 56m
2 stops
MDW1:31 pmChicago Midway
Frontier
Mar 23
MDW5:45 pmChicago Midway
22h 30m
2 stops
SXM5:15 pmSimpson Bay Princess Juliana
Mar 31
SXM6:35 pmSimpson Bay Princess Juliana
19h 56m
2 stops
MDW1:31 pmChicago Midway
Frontier
May 30
MDW9:12 pmChicago Midway
12h 46m
1 stop
SXM10:58 amSimpson Bay Princess Juliana
Jun 14
SXM12:18 pmSimpson Bay Princess Juliana
8h 41m
1 stop
MDW7:59 pmChicago Midway

JetBlue flights from Chicago to St. Maarten

Our best JetBlue deals on Chicago to St. Maarten flight tickets
JetBlue
Jun 7
ORD7:25 pmChicago O'Hare Intl
14h 42m
1 stop
SXM11:07 amSimpson Bay Princess Juliana
Jun 14
SXM12:15 pmSimpson Bay Princess Juliana
12h 24m
1 stop
ORD11:39 pmChicago O'Hare Intl
JetBlue
May 31
ORD7:25 pmChicago O'Hare Intl
14h 42m
1 stop
SXM11:07 amSimpson Bay Princess Juliana
Jun 14
SXM12:15 pmSimpson Bay Princess Juliana
12h 24m
1 stop
ORD11:39 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 month to fly to St. Maarten?

The cheapest month to fly to St. Maarten from Chicago is in September. Flight prices, which tend to average around $589, 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 May is your next best option. Flight prices from Chicago to St. Maarten during May average around $615.

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 $636. 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 $850.

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 evening when prices are around $798.

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?

The ideal time to book your flight to St. Maarten is 21 days in advance when prices tend to average $754. In the past 72 hours, momondo users found flights from Chicago to St. Maarten for as low as $323.

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 61% 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

$127

Fastest flight time

5h 07m

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 $127. The best round-trip flight deal from Chicago to St. Maarten found on momondo in the last 72 hours is $323.
The fastest flight from Chicago to St. Maarten takes 5h 07m
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 $259Free CancellationRating
6.3
8,111 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $553Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $554Free CancellationRating
8.0
8,594 reviews
Search Delta flights
United AirlinesPriceFrom $633Free CancellationRating
7.4
9,028 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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