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Cheap flights from Illinois to St. Maarten from $105

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Illinois to St. Maarten departing on 1/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Illinois to St. Maarten

Cheap round-trip flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
5:15 am - 2:14 pmORD-SXM
6h 59m1 stop
Spirit Airlines Logo
3:09 pm - 11:46 pmSXM-ORD
10h 37m1 stop
$257Spirit Airlines
Find Deal
Sat, Jan 10 - Sat, Jan 17
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
Spirit Airlines Logo
3:09 pm - 11:46 pmSXM-ORD
10h 37m1 stop
$259Spirit Airlines
Find Deal
Wed, Jan 7 - Mon, Jan 12
Spirit Airlines Logo
5:15 am - 2:14 pmORD-SXM
6h 59m1 stop
Spirit Airlines Logo
3:11 pm - 12:18 amSXM-ORD
11h 07m1 stop
$260Spirit Airlines
Find Deal
Mon, Feb 9 - Wed, Feb 18
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:40 pm - 11:42 pmSXM-MDW
9h 02m1 stop
$281Frontier
Find Deal
Sat, Feb 28 - Sat, Mar 7
Frontier Logo
6:00 am - 3:20 pmMDW-SXM
7h 20m1 stop
Frontier Logo
4:30 pm - 11:25 pmSXM-MDW
8h 55m1 stop
$287Frontier
Find Deal
Sat, Feb 21 - Sat, Feb 28
Multiple Airlines Logo
6:00 am - 1:30 pmORD-SXM
29h 30m1 stop
Multiple Airlines Logo
3:09 pm - 11:46 pmSXM-ORD
10h 37m1 stop
$287Multiple Airlines
Find Deal
Fri, Jan 2 - Thu, Jan 8
Delta Logo
6:00 am - 2:55 pmMDW-SXM
6h 55m1 stop
Delta Logo
1:55 pm - 10:22 pmSXM-MDW
10h 27m1 stop
$355Delta
Find Deal
Sun, Jan 25 - Thu, Jan 29
Delta Logo
1:26 pm - 12:30 pmMDW-SXM
21h 04m2 stops
Delta Logo
4:20 pm - 5:55 pmSXM-MDW
27h 35m2 stops
$360Delta
Find Deal
Sun, Jan 25 - Thu, Jan 29
American Airlines Logo
6:02 pm - 12:58 pmSTL-SXM
16h 56m1 stop
American Airlines Logo
2:42 pm - 10:44 pmSXM-STL
10h 02m1 stop
$465American Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23
American Airlines Logo
3:37 pm - 1:42 pmSTL-SXM
20h 05m2 stops
American Airlines Logo
5:33 pm - 9:40 amSXM-STL
18h 07m2 stops
$470American Airlines
Find Deal
Sun, Jan 18 - Fri, Jan 23

Spirit Airlines flights from Illinois to St. Maarten

Our best Spirit Airlines deals on Illinois to St. Maarten flight tickets
Spirit Airlines
Jan 10
ORD5:15 amChicago O'Hare Intl
6h 59m
1 stop
SXM2:14 pmSimpson Bay Princess Juliana
Jan 17
SXM3:09 pmSimpson Bay Princess Juliana
10h 37m
1 stop
ORD11:46 pmChicago O'Hare Intl
$257
Find similar
Spirit Airlines
Jan 7
ORD5:00 amChicago O'Hare Intl
7h 15m
1 stop
SXM2:15 pmSimpson Bay Princess Juliana
Jan 12
SXM3:09 pmSimpson Bay Princess Juliana
10h 37m
1 stop
ORD11:46 pmChicago O'Hare Intl
$259
Find similar
Spirit Airlines
Feb 9
ORD5:15 amChicago O'Hare Intl
6h 59m
1 stop
SXM2:14 pmSimpson Bay Princess Juliana
Feb 18
SXM3:11 pmSimpson Bay Princess Juliana
11h 07m
1 stop
ORD12:18 amChicago O'Hare Intl
$260
Find similar

Delta flights from Illinois to St. Maarten

Our best Delta deals on Illinois to St. Maarten flight tickets
Delta
Jan 25
MDW6:00 amChicago Midway
6h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
Jan 29
SXM1:55 pmSimpson Bay Princess Juliana
10h 27m
1 stop
MDW10:22 pmChicago Midway
$355
Find similar
Delta
Jan 25
MDW6:00 amChicago Midway
28h 30m
2 stops
SXM12:30 pmSimpson Bay Princess Juliana
Jan 29
SXM4:20 pmSimpson Bay Princess Juliana
27h 35m
2 stops
MDW5:55 pmChicago Midway
$360
Find similar
Delta
Jan 10
MDW6:45 amChicago Midway
7h 18m
1 stop
SXM4:03 pmSimpson Bay Princess Juliana
Jan 21
SXM1:55 pmSimpson Bay Princess Juliana
10h 27m
1 stop
MDW10:22 pmChicago Midway
$458
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Illinois 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 November 23, 2025.
Use the filters below to find and compare flights from Illinois 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 1/10

5:15 am-2:14 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Sat 1/17

3:09 pm-11:46 pm

1 stop10h 37m

$257

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Wed 1/7

5:00 am-2:15 pm

1 stop7h 15m

Simpson Bay Princess Juliana

Mon 1/12

3:09 pm-11:46 pm

1 stop10h 37m

$259

ChicagoSimpson Bay

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Mon 2/9

5:15 am-2:14 pm

1 stop6h 59m

Simpson Bay Princess Juliana

Wed 2/18

3:11 pm-12:18 am

1 stop11h 07m

$260

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/28

6:00 am-3:20 pm

1 stop7h 20m

Simpson Bay Princess Juliana

Sat 3/7

4:40 pm-11:42 pm

1 stop9h 02m

$281

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

ORD - SXM

ORDSXM

Chicago O'Hare Intl

Fri 1/2

6:00 am-1:30 pm

1 stop29h 30m

Simpson Bay Princess Juliana

Thu 1/8

3:09 pm-11:46 pm

1 stop10h 37m

$287

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Thu 1/29

1:55 pm-10:22 pm

1 stop10h 27m

$355

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 1/25

1:26 pm-12:30 pm

2 stops21h 04m

Simpson Bay Princess Juliana

Thu 1/29

4:20 pm-5:55 pm

2 stops27h 35m

$360

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 1/18

6:02 pm-12:58 pm

1 stop16h 56m

Simpson Bay Princess Juliana

Fri 1/23

2:42 pm-10:44 pm

1 stop10h 02m

$465

St. LouisSimpson Bay

STL - SXM

STLSXM

Lambert-St Louis

Sun 1/18

3:37 pm-1:42 pm

2 stops20h 05m

Simpson Bay Princess Juliana

Fri 1/23

5:33 pm-9:40 am

2 stops18h 07m

$470

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 Illinois 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 Illinois 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 Illinois 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 Illinois. 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 $892.

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 Illinois 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 $876.

What is the cheapest Illinois to St. Maarten flight route?

Fly from Chicago O'Hare Intl to Simpson Bay Princess Juliana for the best Illinois - 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 Illinois when booking weeks ahead of your departure date. In general, you can expect to find flights to St. Maarten for around $693 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to St. Maarten from Illinois for as low as $524 on momondo.

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

There are 2 cabin classes available to choose from on Illinois 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 Illinois to St. Maarten flights?

No. A direct flight is the cheapest option for a flight between Illinois to St. Maarten.

Cheap Illinois to St. Maarten flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Illinois to St. Maarten

Best Price Found

$420

Fastest flight time

4h 45m

Direct flights

Mon and Sun

Airports in St. Maarten

1 airport
The best flight deal from Illinois to St. Maarten found on momondo in the last 72 hours is $420
The fastest flight from Illinois to St. Maarten takes 4h 45m
Direct flights go from Illinois 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 Illinois to St. Maarten?

    Prices for flights from Illinois to St. Maarten are updated daily.

  • How many operators does momondo search for flights from Illinois to St. Maarten?

  • How old do you have to be to fly from Illinois 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 Illinois to St. Maarten.

  • What documentation or ID do you need to fly to St. Maarten?

    The required travel and health documents for your St. Maarten trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at St. Maarten. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from Illinois to St. Maarten?

Best airlines flying from Illinois to St. Maarten

Compare and see reviews for airlines that fly from Illinois to St. Maarten with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $316Free CancellationRating
6.3
8,160 reviews
Search Spirit Airlines flights
DeltaPriceFrom $318Free CancellationRating
7.9
8,000 reviews
Search Delta flights
United AirlinesPriceFrom $420Free CancellationRating
7.4
9,036 reviews
Search United Airlines flights
JetBluePriceFrom $535Free CancellationRating
7.2
2,901 reviews
Search JetBlue flights
American AirlinesPriceFrom $585Free CancellationRating
7.2
11,047 reviews
Search American Airlines flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Illinois to St. Maarten. Millions of users trust and use momondo every year so you are in good hands.

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

Flights from Illinois to St. Maarten with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Illinois to St. Maarten?

Once you have performed a search for Illinois to St. Maarten flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Illinois to St. Maarten right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Illinois 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 cities in St. Maarten

Popular flights according to clicks in the last 7 days on momondo
Flights to Simpson Bayfrom $178