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Cheap flights from St. Maarten to Chicago from $197

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from St. Maarten to Chicago departing on 12/24. 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 St. Maarten to Chicago

Recent round-trip flight deals from St. Maarten to Chicago

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:20 pm - 11:13 pmSXM-ORD
9h 53m1 stop
Multiple Airlines Logo
11:48 am - 2:15 pmORD-SXM
24h 27m1 stop
$374Multiple Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Spirit Airlines Logo
3:20 pm - 9:01 amSXM-ORD
19h 41m2 stops
Spirit Airlines Logo
5:00 am - 2:15 pmORD-SXM
7h 15m1 stop
$397Spirit Airlines
Find Deal
Sat, Nov 22 - Sat, Nov 29
Spirit Airlines Logo
3:20 pm - 11:13 pmSXM-ORD
9h 53m1 stop
Spirit Airlines Logo
3:53 pm - 2:15 pmORD-SXM
20h 22m2 stops
$416Spirit Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
United Airlines Logo
2:52 pm - 11:13 pmSXM-ORD
10h 21m1 stop
United Airlines Logo
6:25 pm - 1:50 pmORD-SXM
17h 25m1 stop
$509United Airlines
Find Deal
Sat, Feb 14 - Sat, Feb 21
American Airlines Logo
3:00 pm - 6:54 pmSXM-ORD
5h 54mnonstop
American Airlines Logo
6:59 pm - 12:40 pmORD-SXM
15h 41m1 stop
$584American Airlines
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Sat, Feb 14 - Sat, Feb 21
United Airlines Logo
4:55 pm - 9:44 amSXM-ORD
18h 49m1 stop
United Airlines Logo
9:05 pm - 12:50 pmORD-SXM
14h 45m1 stop
$587United Airlines
Find Deal
Fri, Mar 6 - Tue, Mar 10
American Airlines Logo
5:05 pm - 11:40 pmSXM-ORD
8h 35m1 stop
American Airlines Logo
5:00 am - 4:22 pmORD-SXM
9h 22m1 stop
$625American Airlines
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Sat, Nov 22 - Sat, Nov 29
Delta Logo
4:26 pm - 3:23 pmSXM-MDW
24h 57m2 stops
Delta Logo
6:00 am - 1:53 pmMDW-SXM
6h 53m1 stop
$632Delta
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Fri, Mar 6 - Tue, Mar 10
Lufthansa Logo
5:00 pm - 7:41 amSXM-ORD
16h 41m1 stop
Lufthansa Logo
8:45 am - 3:57 pmORD-SXM
5h 12mnonstop
$635Lufthansa
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Sat, Nov 22 - Sat, Nov 29
Delta Logo
4:26 pm - 3:23 pmSXM-MDW
24h 57m2 stops
Delta Logo
9:20 am - 11:15 amMDW-SXM
24h 55m2 stops
$722Delta
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Fri, Mar 6 - Tue, Mar 10

United Airlines flights from St. Maarten to Chicago

Our best United Airlines deals on St. Maarten to Chicago flight tickets
United Airlines
Feb 14
SXM2:52 pmSimpson Bay Princess Juliana
10h 21m
1 stop
ORD11:13 pmChicago O'Hare Intl
Feb 21
ORD6:25 pmChicago O'Hare Intl
17h 25m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$509
Find similar
United Airlines
Mar 6
SXM4:55 pmSimpson Bay Princess Juliana
18h 49m
1 stop
ORD9:44 amChicago O'Hare Intl
Mar 10
ORD9:05 pmChicago O'Hare Intl
14h 45m
1 stop
SXM12:50 pmSimpson Bay Princess Juliana
$587
Find similar
United Airlines
Nov 22
SXM2:40 pmSimpson Bay Princess Juliana
6h 00m
ORD6:40 pmChicago O'Hare Intl
Nov 29
ORD8:45 amChicago O'Hare Intl
5h 12m
SXM3:57 pmSimpson Bay Princess Juliana
$689
Find similar

American Airlines flights from St. Maarten to Chicago

Our best American Airlines deals on St. Maarten to Chicago flight tickets
American Airlines
Feb 14
SXM3:00 pmSimpson Bay Princess Juliana
5h 54m
ORD6:54 pmChicago O'Hare Intl
Feb 21
ORD6:59 pmChicago O'Hare Intl
15h 41m
1 stop
SXM12:40 pmSimpson Bay Princess Juliana
$584
Find similar
American Airlines
Nov 22
SXM5:05 pmSimpson Bay Princess Juliana
8h 35m
1 stop
ORD11:40 pmChicago O'Hare Intl
Nov 29
ORD5:00 amChicago O'Hare Intl
9h 22m
1 stop
SXM4:22 pmSimpson Bay Princess Juliana
$625
Find similar
American Airlines
Feb 14
SXM3:00 pmSimpson Bay Princess Juliana
5h 54m
ORD6:54 pmChicago O'Hare Intl
Feb 21
ORD6:59 pmChicago O'Hare Intl
15h 41m
1 stop
SXM12:40 pmSimpson Bay Princess Juliana
$629
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from St. Maarten to Chicago 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 4, 2025.
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/21

3:20 pm-11:13 pm

1 stop9h 53m

Chicago O'Hare Intl

Sun 11/23

11:48 am-2:15 pm

1 stop24h 27m

$374

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

3:20 pm-9:01 am

2 stops19h 41m

Chicago O'Hare Intl

Sat 11/29

5:00 am-2:15 pm

1 stop7h 15m

$397

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 11/21

3:20 pm-11:13 pm

1 stop9h 53m

Chicago O'Hare Intl

Sun 11/23

3:53 pm-2:15 pm

2 stops20h 22m

$416

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

2:52 pm-11:13 pm

1 stop10h 21m

Chicago O'Hare Intl

Sat 2/21

6:25 pm-1:50 pm

1 stop17h 25m

$509

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 2/14

3:00 pm-6:54 pm

Nonstop5h 54m

Chicago O'Hare Intl

Sat 2/21

6:59 pm-12:40 pm

1 stop15h 41m

$584

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 3/6

4:55 pm-9:44 am

1 stop18h 49m

Chicago O'Hare Intl

Tue 3/10

9:05 pm-12:50 pm

1 stop14h 45m

$587

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

5:05 pm-11:40 pm

1 stop8h 35m

Chicago O'Hare Intl

Sat 11/29

5:00 am-4:22 pm

1 stop9h 22m

$625

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:23 pm

2 stops24h 57m

Chicago Midway

Tue 3/10

6:00 am-1:53 pm

1 stop6h 53m

$632

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 11/22

5:00 pm-7:41 am

1 stop16h 41m

Chicago O'Hare Intl

Sat 11/29

8:45 am-3:57 pm

Nonstop5h 12m

$635

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:23 pm

2 stops24h 57m

Chicago Midway

Tue 3/10

9:20 am-11:15 am

2 stops24h 55m

$722

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 Chicago from

How to get the cheapest flight ticket from St. Maarten to Chicago

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 Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as $372. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from St. Maarten to Chicago for around $773.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from St. Maarten to Chicago during this time can be as low as $402. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $614.

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

Fly from Simpson Bay Princess Juliana to Chicago O'Hare Intl for the best St. Maarten - Chicago flight prices

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

There are 3 cabin classes available to choose from on St. Maarten to Chicago 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 St. Maarten to Chicago flights?

You could potentially save up to 5% on your flight if you consider stops on a St. Maarten to Chicago flight.

Cheap St. Maarten to Chicago flight deals and tips

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

Fastest flight time

5h 39m

Direct flights

Mon and Sun

Airports in Chicago

1 airport
The fastest flight from St. Maarten to Chicago takes 5h 39m
Direct flights go from St. Maarten to Chicago on Monday and Sunday. There are no airlines offering direct flights.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
Search flight deals

  • When did momondo last update prices for flights from St. Maarten to Chicago?

    Prices for flights from St. Maarten to Chicago were last updated today.

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from St. Maarten to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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

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

All flight searches from St. Maarten to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from St. Maarten.

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

Yes. momondo can track prices for St. Maarten to Chicago 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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport