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Cheap flights from St. Maarten to Chicago from $206

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 3/16. 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
12:25 pm - 11:59 pm
SXM
-
ORD
12h 34m
2 stops
Multiple Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$345Multiple Airlines
Thu, Apr 23 - Sun, May 3
Spirit Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Spirit Airlines Logo
5:05 am - 1:37 pm
ORD
-
SXM
7h 32m
1 stop
$370Spirit Airlines
Thu, Apr 23 - Sun, May 3
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
1:27 pm - 1:37 pm
ORD
-
SXM
23h 10m
1 stop
$407Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
5:57 pm - 1:37 pm
ORD
-
SXM
42h 40m
2 stops
$419Multiple Airlines
Sat, Apr 18 - Tue, Apr 28
Multiple Airlines Logo
2:42 pm - 12:24 am
SXM
-
ORD
10h 42m
1 stop
Multiple Airlines Logo
12:53 pm - 11:20 am
ORD
-
SXM
21h 27m
2 stops
$424Multiple Airlines
Sat, Apr 18 - Sat, Apr 25
Air Canada Logo
4:00 pm - 6:58 pm
SXM
-
ORD
27h 58m
2 stops
Air Canada Logo
2:00 pm - 2:55 pm
ORD
-
SXM
23h 55m
1 stop
$445Air Canada
Fri, Apr 17 - Sun, Apr 26
Southwest Logo
2:25 pm - 12:05 am
SXM
-
MDW
10h 40m
1 stop
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
$539Southwest
Thu, Apr 23 - Sun, May 3
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
$544Southwest
Thu, Apr 23 - Sun, May 3
Delta Logo
1:35 pm - 10:28 pm
SXM
-
MDW
9h 53m
1 stop
Delta Logo
6:00 am - 2:05 pm
MDW
-
SXM
7h 05m
1 stop
$625Delta
Fri, Apr 17 - Tue, Apr 28
Delta Logo
1:35 pm - 10:28 pm
SXM
-
MDW
9h 53m
1 stop
Delta Logo
10:41 am - 12:10 pm
MDW
-
SXM
24h 29m
2 stops
$630Delta
Fri, Apr 17 - Tue, Apr 28

Air Canada flights from St. Maarten to Chicago

Our best Air Canada deals on St. Maarten to Chicago flight tickets
Air Canada
Apr 17
SXM4:00 pmSimpson Bay Princess Juliana
27h 58m
2 stops
ORD6:58 pmChicago O'Hare Intl
Apr 26
ORD2:00 pmChicago O'Hare Intl
23h 55m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$445
Air Canada
Apr 20
SXM4:00 pmSimpson Bay Princess Juliana
19h 53m
2 stops
ORD10:53 amChicago O'Hare Intl
Apr 26
ORD9:50 amChicago O'Hare Intl
28h 05m
1 stop
SXM2:55 pmSimpson Bay Princess Juliana
$448
Air Canada
Apr 17
SXM4:00 pmSimpson Bay Princess Juliana
16h 58m
2 stops
ORD7:58 amChicago O'Hare Intl
Apr 24
ORD6:21 pmChicago O'Hare Intl
19h 34m
2 stops
SXM2:55 pmSimpson Bay Princess Juliana
$464

Spirit Airlines flights from St. Maarten to Chicago

Our best Spirit Airlines deals on St. Maarten to Chicago flight tickets
Spirit Airlines
Apr 23
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
May 3
ORD5:05 amChicago O'Hare Intl
7h 32m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$370
Spirit Airlines
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
10h 42m
1 stop
ORD12:24 amChicago O'Hare Intl
Apr 26
ORD5:05 amChicago O'Hare Intl
7h 32m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$431
Spirit Airlines
Apr 18
SXM2:42 pmSimpson Bay Princess Juliana
20h 41m
2 stops
ORD10:23 amChicago O'Hare Intl
Apr 26
ORD5:05 amChicago O'Hare Intl
7h 32m
1 stop
SXM1:37 pmSimpson Bay Princess Juliana
$458

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 March 1, 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

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

12:25 pm-11:59 pm

2 stops12h 34m

Chicago O'Hare Intl

Sun 5/3

5:05 am-1:30 pm

1 stop7h 25m

$345

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Thu 4/23

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sun 5/3

5:05 am-1:37 pm

1 stop7h 32m

$370

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

1:27 pm-1:37 pm

1 stop23h 10m

$407

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Tue 4/28

5:57 pm-1:37 pm

2 stops42h 40m

$419

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 4/18

2:42 pm-12:24 am

1 stop10h 42m

Chicago O'Hare Intl

Sat 4/25

12:53 pm-11:20 am

2 stops21h 27m

$424

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Fri 4/17

4:00 pm-6:58 pm

2 stops27h 58m

Chicago O'Hare Intl

Sun 4/26

2:00 pm-2:55 pm

1 stop23h 55m

$445

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:25 pm-12:05 am

1 stop10h 40m

Chicago Midway

Sun 5/3

5:05 am-2:25 pm

1 stop8h 20m

$539

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Sun 5/3

8:55 pm-1:30 pm

2 stops15h 35m

$544

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/17

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Tue 4/28

6:00 am-2:05 pm

1 stop7h 05m

$625

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/17

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Tue 4/28

10:41 am-12:10 pm

2 stops24h 29m

$630

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 Saturday, the most expensive travel day of the week, you can expect to see flight prices from St. Maarten to Chicago for around $610.

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 66% 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 46m

Direct flights

Mon and Sun

Airports in Chicago

3 airports
The fastest flight from St. Maarten to Chicago takes 5h 46m
Direct flights go from St. Maarten to Chicago on Monday 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

  • 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
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?

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