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Cheap flights from St. Maarten to Chicago from $252

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 10/15. 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.
Air Canada Logo
3:45 pm - 9:23 am
SXM
-
ORD
18h 38m
1 stop
Air Canada Logo
9:05 pm - 3:45 pm
ORD
-
SXM
17h 40m
1 stop
$440Air Canada
Sun, Oct 25 - Sat, Oct 31
Air Canada Logo
3:45 pm - 11:07 am
SXM
-
ORD
20h 22m
2 stops
Air Canada Logo
4:30 pm - 3:45 pm
ORD
-
SXM
22h 15m
1 stop
$444Air Canada
Sun, Oct 25 - Sat, Oct 31
Air Canada Logo
3:45 pm - 11:07 am
SXM
-
ORD
20h 22m
2 stops
Air Canada Logo
3:45 pm - 3:45 pm
ORD
-
SXM
23h 00m
2 stops
$447Air Canada
Sun, Oct 25 - Sat, Oct 31
Air Canada Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Air Canada Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
$464Air Canada
Sat, Sep 5 - Fri, Sep 11
Air Canada Logo
6:00 pm - 10:19 am
SXM
-
ORD
17h 19m
2 stops
Air Canada Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
$467Air Canada
Sat, Sep 5 - Fri, Sep 11
Southwest Logo
1:55 pm - 9:00 pm
SXM
-
MDW
8h 05m
1 stop
Southwest Logo
7:55 pm - 12:55 pm
MDW
-
SXM
16h 00m
2 stops
$521Southwest
Sat, Sep 5 - Fri, Sep 11
Southwest Logo
1:55 pm - 9:00 pm
SXM
-
MDW
8h 05m
1 stop
Southwest Logo
5:00 am - 2:05 pm
MDW
-
SXM
8h 05m
1 stop
$566Southwest
Sat, Sep 5 - Fri, Sep 11
Delta Logo
3:14 pm - 10:25 pm
SXM
-
MDW
8h 11m
1 stop
Delta Logo
6:00 am - 1:49 pm
MDW
-
SXM
6h 49m
1 stop
$656Delta
Fri, Oct 23 - Sat, Oct 31
Delta Logo
3:14 pm - 10:25 pm
SXM
-
MDW
8h 11m
1 stop
Delta Logo
6:00 am - 2:49 pm
MDW
-
SXM
6h 49m
1 stop
$665Delta
Thu, Oct 22 - Mon, Nov 2
Multiple Airlines Logo
6:00 pm - 11:00 am
SXM
-
MDW
18h 00m
1 stop
Multiple Airlines Logo
5:03 pm - 5:00 pm
MDW
-
SXM
22h 57m
3 stops
$1,028Multiple Airlines
Sat, Sep 5 - Fri, Sep 11

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United Airlines flights from St. Maarten to Chicago

Our best United Airlines deals on St. Maarten to Chicago flight tickets
United Airlines
Oct 27
SXM1:52 pmSimpson Bay Princess Juliana
9h 26m
1 stop
ORD10:18 pmChicago O'Hare Intl
Nov 1
ORD7:00 amChicago O'Hare Intl
28h 50m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$687
United Airlines
Oct 25
SXM1:52 pmSimpson Bay Princess Juliana
18h 39m
1 stop
ORD7:31 amChicago O'Hare Intl
Oct 31
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM2:57 pmSimpson Bay Princess Juliana
$741
United Airlines
Oct 25
SXM1:52 pmSimpson Bay Princess Juliana
9h 26m
1 stop
ORD10:18 pmChicago O'Hare Intl
Oct 28
ORD9:35 pmChicago O'Hare Intl
14h 15m
1 stop
SXM12:50 pmSimpson Bay Princess Juliana
$745

Air Canada flights from St. Maarten to Chicago

Our best Air Canada deals on St. Maarten to Chicago flight tickets
Air Canada
Oct 25
SXM3:45 pmSimpson Bay Princess Juliana
18h 38m
1 stop
ORD9:23 amChicago O'Hare Intl
Oct 31
ORD9:05 pmChicago O'Hare Intl
17h 40m
1 stop
SXM3:45 pmSimpson Bay Princess Juliana
$440
Air Canada
Oct 25
SXM3:45 pmSimpson Bay Princess Juliana
20h 22m
2 stops
ORD11:07 amChicago O'Hare Intl
Oct 31
ORD4:30 pmChicago O'Hare Intl
22h 15m
1 stop
SXM3:45 pmSimpson Bay Princess Juliana
$444
Air Canada
Oct 25
SXM3:45 pmSimpson Bay Princess Juliana
20h 22m
2 stops
ORD11:07 amChicago O'Hare Intl
Oct 31
ORD3:45 pmChicago O'Hare Intl
23h 00m
2 stops
SXM3:45 pmSimpson Bay Princess Juliana
$447

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 July 26, 2026.
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

Cheapest round-trip

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/25

3:45 pm-9:23 am

1 stop18h 38m

Chicago O'Hare Intl

Sat 10/31

9:05 pm-3:45 pm

1 stop17h 40m

$440

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/25

3:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Sat 10/31

4:30 pm-3:45 pm

1 stop22h 15m

$444

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 10/25

3:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Sat 10/31

3:45 pm-3:45 pm

2 stops23h 00m

$447

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/5

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 9/11

8:40 pm-5:00 pm

1 stop19h 20m

$464

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 9/5

6:00 pm-10:19 am

2 stops17h 19m

Chicago O'Hare Intl

Fri 9/11

8:40 pm-5:00 pm

1 stop19h 20m

$467

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/5

1:55 pm-9:00 pm

1 stop8h 05m

Chicago Midway

Fri 9/11

7:55 pm-12:55 pm

2 stops16h 00m

$521

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/5

1:55 pm-9:00 pm

1 stop8h 05m

Chicago Midway

Fri 9/11

5:00 am-2:05 pm

1 stop8h 05m

$566
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 10/23

3:14 pm-10:25 pm

1 stop8h 11m

Chicago Midway

Sat 10/31

6:00 am-1:49 pm

1 stop6h 49m

$656

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 10/22

3:14 pm-10:25 pm

1 stop8h 11m

Chicago Midway

Mon 11/2

6:00 am-2:49 pm

1 stop6h 49m

$665

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 9/5

6:00 pm-11:00 am

1 stop18h 00m

Chicago Midway

Fri 9/11

5:03 pm-5:00 pm

3 stops22h 57m

$1,028

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 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 is only 1 cabin class 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 3% 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

8h 05m

Direct flights

Mon, Tue, Fri and Sun

Airports in Chicago

3 airports
The fastest flight from St. Maarten to Chicago takes 8h 05m
Direct flights go from St. Maarten to Chicago on Monday, Tuesday, Friday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From St. Maarten there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from St. Maarten to Chicago

  • 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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