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Cheap flights from St. Maarten to Chicago from $239

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 7/9. 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
1 adult, Economy, 0 bags

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.
Southwest Logo
2:25 pm - 9:25 pm
SXM
-
MDW
8h 00m
1 stop
Southwest Logo
8:50 pm - 3:05 pm
MDW
-
SXM
17h 15m
2 stops
$542Southwest
vie., jul. 17 - vie., jul. 24
Southwest Logo
2:25 pm - 7:15 am
SXM
-
MDW
17h 50m
2 stops
Southwest Logo
8:50 pm - 3:05 pm
MDW
-
SXM
17h 15m
2 stops
$570Southwest
vie., jul. 17 - vie., jul. 24
Southwest Logo
2:15 pm - 11:20 pm
SXM
-
MDW
10h 05m
2 stops
Southwest Logo
6:15 pm - 12:55 pm
MDW
-
SXM
17h 40m
2 stops
$652Southwest
sáb., ago. 1 - vie., ago. 7
Delta Logo
3:20 pm - 10:15 pm
SXM
-
MDW
7h 55m
1 stop
Delta Logo
6:05 am - 1:53 pm
MDW
-
SXM
6h 48m
1 stop
$656Delta
sáb., ago. 1 - vie., ago. 7
Southwest Logo
2:15 pm - 11:45 pm
SXM
-
MDW
10h 30m
1 stop
Southwest Logo
6:15 pm - 12:55 pm
MDW
-
SXM
17h 40m
2 stops
$672Southwest
sáb., ago. 1 - vie., ago. 7
Southwest Logo
2:25 pm - 12:45 am
SXM
-
MDW
11h 20m
1 stop
Southwest Logo
5:10 am - 1:25 pm
MDW
-
SXM
7h 15m
1 stop
$769Southwest
vie., jul. 17 - vie., jul. 24

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Southwest flights from St. Maarten to Chicago Midway Airport

Our best Southwest deals on St. Maarten to Chicago Midway Airport flight tickets
Southwest
Jul 17
SXM2:25 pmSimpson Bay Princess Juliana
8h 00m
1 stop
MDW9:25 pmChicago Midway
Jul 24
MDW8:50 pmChicago Midway
17h 15m
2 stops
SXM3:05 pmSimpson Bay Princess Juliana
$542
Southwest
Jul 17
SXM2:25 pmSimpson Bay Princess Juliana
17h 50m
2 stops
MDW7:15 amChicago Midway
Jul 24
MDW8:50 pmChicago Midway
17h 15m
2 stops
SXM3:05 pmSimpson Bay Princess Juliana
$570
Southwest
Aug 1
SXM2:15 pmSimpson Bay Princess Juliana
10h 05m
2 stops
MDW11:20 pmChicago Midway
Aug 7
MDW6:15 pmChicago Midway
17h 40m
2 stops
SXM12:55 pmSimpson Bay Princess Juliana
$652

momondo Fare Finder

 
Customize your flight search to find flights from St. Maarten to Chicago Midway Airport 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 junio 13, 2026.
Use the filters below to find and compare flights from St. Maarten to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

vie. 7/17

2:25 pm-9:25 pm

1 stop8h 00m

Chicago Midway

vie. 7/24

8:50 pm-3:05 pm

2 stops17h 15m

$542

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

vie. 7/17

2:25 pm-7:15 am

2 stops17h 50m

Chicago Midway

vie. 7/24

8:50 pm-3:05 pm

2 stops17h 15m

$570

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 8/1

2:15 pm-11:20 pm

2 stops10h 05m

Chicago Midway

vie. 8/7

6:15 pm-12:55 pm

2 stops17h 40m

$652
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 8/1

3:20 pm-10:15 pm

1 stop7h 55m

Chicago Midway

vie. 8/7

6:05 am-1:53 pm

1 stop6h 48m

$656

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 8/1

2:15 pm-11:45 pm

1 stop10h 30m

Chicago Midway

vie. 8/7

6:15 pm-12:55 pm

2 stops17h 40m

$672

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

vie. 7/17

2:25 pm-12:45 am

1 stop11h 20m

Chicago Midway

vie. 7/24

5:10 am-1:25 pm

1 stop7h 15m

$769
Cheapest one-way
Quickest one-way

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

jue. 7/9

2:25 pm-9:25 pm

1 stop8h 00m

$239

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

jue. 7/9

2:25 pm-7:10 am

2 stops17h 45m

$275

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

vie. 7/10

2:25 pm-12:45 am

1 stop11h 20m

$320

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

vie. 7/10

2:25 pm-12:10 am

2 stops10h 45m

$339

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
1
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See travel insights to Chicago from

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

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 airline that flies from St. Maarten to Chicago Midway?

Southwest is the most popular carrier operating from St. Maarten to Chicago Midway

Cheap St. Maarten to Chicago Midway Airport flight deals and tips

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

Fastest flight time

11h 20m

Direct flights

None
The fastest flight from St. Maarten to Chicago Midway Airport takes 11h 20m
There are no direct flights from St. Maarten to Chicago Midway Airport. There are no popular flight routes from St. Maarten to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from St. Maarten to Chicago Midway Airport

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

    Prices for flights from St. Maarten to Chicago Midway Airport refresh daily.

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

    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 St. Maarten to Chicago Midway Airport.

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

    The necessary travel and health documents for your Chicago Midway Airport 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.

Traveling to a place near Chicago?

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

Why use momondo?

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

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from St. Maarten to Chicago for you.

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

Yes. All flights to Chicago from St. Maarten on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

momondo helps you find the best flight between St. Maarten and Chicago 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 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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1 adult
lun. 7/13
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