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Cheap flights from St. Maarten to Chicago from $208

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 5/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
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
6:00 pm - 9:50 am
SXM
-
ORD
16h 50m
1 stop
Air Canada Logo
8:40 pm - 5:00 pm
ORD
-
SXM
19h 20m
1 stop
$400Air Canada
Sat, Jun 13 - Fri, Jun 19
Multiple Airlines Logo
3:20 pm - 9:00 am
SXM
-
ORD
18h 40m
1 stop
Multiple Airlines Logo
8:20 pm - 5:00 pm
ORD
-
SXM
19h 40m
1 stop
$492Multiple Airlines
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
3:20 pm - 12:11 pm
SXM
-
ORD
21h 51m
2 stops
Multiple Airlines Logo
8:20 pm - 5:00 pm
ORD
-
SXM
19h 40m
1 stop
$523Multiple Airlines
Mon, Jun 1 - Wed, Jun 10
Multiple Airlines Logo
6:00 pm - 9:00 am
SXM
-
ORD
16h 00m
1 stop
Multiple Airlines Logo
1:57 pm - 5:00 pm
ORD
-
SXM
26h 03m
2 stops
$534Multiple Airlines
Sat, Jun 13 - Fri, Jun 19
Spirit Airlines Logo
2:35 pm - 8:22 am
SXM
-
ORD
18h 47m
1 stop
Spirit Airlines Logo
5:05 am - 1:30 pm
ORD
-
SXM
7h 25m
1 stop
$584Spirit Airlines
Sun, Jun 7 - Sun, Jun 14
Delta Logo
3:18 pm - 10:15 pm
SXM
-
MDW
7h 57m
1 stop
Delta Logo
6:05 am - 1:53 pm
MDW
-
SXM
6h 48m
1 stop
$681Delta
Tue, Jul 28 - Thu, Aug 6
Southwest Logo
1:55 pm - 11:45 pm
SXM
-
MDW
10h 50m
1 stop
Southwest Logo
9:05 pm - 1:25 pm
MDW
-
SXM
15h 20m
2 stops
$685Southwest
Sun, Jun 7 - Sun, Jun 14
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
Southwest Logo
5:20 am - 3:30 pm
MDW
-
SXM
9h 10m
1 stop
$695Southwest
Wed, Jun 3 - Sun, Jun 7
Delta Logo
3:18 pm - 10:17 pm
SXM
-
MDW
7h 59m
1 stop
Delta Logo
6:05 am - 1:53 pm
MDW
-
SXM
6h 48m
1 stop
$706Delta
Sat, Jun 13 - Fri, Jun 19
Southwest Logo
3:00 pm - 8:40 am
SXM
-
MDW
18h 40m
2 stops
Southwest Logo
8:45 pm - 2:05 pm
MDW
-
SXM
16h 20m
2 stops
$710Southwest
Tue, Jul 28 - Thu, Aug 6

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Delta flights from St. Maarten to Chicago

Our best Delta deals on St. Maarten to Chicago flight tickets
Delta
Jul 2
SXM3:18 pmSimpson Bay Princess Juliana
9h 41m
1 stop
ORD11:59 pmChicago O'Hare Intl
Jul 7
ORD5:15 amChicago O'Hare Intl
7h 38m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
$656
Delta
Jul 28
SXM3:18 pmSimpson Bay Princess Juliana
7h 57m
1 stop
MDW10:15 pmChicago Midway
Aug 6
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
$681
Delta
Jun 13
SXM3:18 pmSimpson Bay Princess Juliana
7h 59m
1 stop
MDW10:17 pmChicago Midway
Jun 19
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
$706

American Airlines flights from St. Maarten to Chicago

Our best American Airlines deals on St. Maarten to Chicago flight tickets
American Airlines
Jul 2
SXM4:46 pmSimpson Bay Princess Juliana
15h 06m
2 stops
ORD6:52 amChicago O'Hare Intl
Jul 7
ORD6:10 amChicago O'Hare Intl
8h 36m
1 stop
SXM3:46 pmSimpson Bay Princess Juliana
$670
American Airlines
Jul 28
SXM4:46 pmSimpson Bay Princess Juliana
17h 24m
1 stop
ORD9:10 amChicago O'Hare Intl
Aug 6
ORD8:58 pmChicago O'Hare Intl
15h 44m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
$695
American Airlines
Jul 28
SXM4:46 pmSimpson Bay Princess Juliana
15h 06m
2 stops
ORD6:52 amChicago O'Hare Intl
Aug 6
ORD8:58 pmChicago O'Hare Intl
15h 44m
2 stops
SXM1:42 pmSimpson Bay Princess Juliana
$735

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 April 25, 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

Sat 6/13

6:00 pm-9:50 am

1 stop16h 50m

Chicago O'Hare Intl

Fri 6/19

8:40 pm-5:00 pm

1 stop19h 20m

$400

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 6/1

3:20 pm-9:00 am

1 stop18h 40m

Chicago O'Hare Intl

Wed 6/10

8:20 pm-5:00 pm

1 stop19h 40m

$492

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Mon 6/1

3:20 pm-12:11 pm

2 stops21h 51m

Chicago O'Hare Intl

Wed 6/10

8:20 pm-5:00 pm

1 stop19h 40m

$523

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sat 6/13

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Fri 6/19

1:57 pm-5:00 pm

2 stops26h 03m

$534

Simpson BayChicago

SXM - ORD

SXMORD

Simpson Bay Princess Juliana

Sun 6/7

2:35 pm-8:22 am

1 stop18h 47m

Chicago O'Hare Intl

Sun 6/14

5:05 am-1:30 pm

1 stop7h 25m

$584
Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 7/28

3:18 pm-10:15 pm

1 stop7h 57m

Chicago Midway

Thu 8/6

6:05 am-1:53 pm

1 stop6h 48m

$681

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 6/7

1:55 pm-11:45 pm

1 stop10h 50m

Chicago Midway

Sun 6/14

9:05 pm-1:25 pm

2 stops15h 20m

$685

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 6/3

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Sun 6/7

5:20 am-3:30 pm

1 stop9h 10m

$695

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 6/13

3:18 pm-10:17 pm

1 stop7h 59m

Chicago Midway

Fri 6/19

6:05 am-1:53 pm

1 stop6h 48m

$706

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 7/28

3:00 pm-8:40 am

2 stops18h 40m

Chicago Midway

Thu 8/6

8:45 pm-2:05 pm

2 stops16h 20m

$710

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 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 54% 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

7h 57m

Direct flights

None
The fastest flight from St. Maarten to Chicago takes 7h 57m
There are no direct flights from St. Maarten to Chicago. Popular non-direct route for this connection is Simpson Bay Princess Juliana Airport - Chicago O'Hare Intl Airport.
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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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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