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Cheap flights from St. Maarten to Chicago from $238

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
4:45 pm - 9:08 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
18h 23m1 stop Toronto Pearson Intl
Air Canada Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$449Air Canada
Fri, Jan 15 - Fri, Jan 22
Air Canada Logo
4:45 pm - 11:07 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 22m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
1:55 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
22h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$452Air Canada
Fri, Jan 15 - Fri, Jan 22
American Airlines Logo
5:33 pm - 12:44 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
9h 11m1 stop Miami
American Airlines Logo
6:00 am - 4:31 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 31m1 stop Miami
$457American Airlines
Fri, Nov 6 - Mon, Nov 9
American Airlines Logo
3:26 pm - 11:56 pmSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
10h 30m1 stop Miami
American Airlines Logo
6:00 am - 4:31 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 31m1 stop Miami
$457American Airlines
Fri, Nov 6 - Mon, Nov 9
Air Canada Logo
4:45 pm - 9:08 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
18h 23m1 stop Toronto Pearson Intl
Air Canada Logo
8:50 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
16h 55m1 stop Toronto Pearson Intl
$457Air Canada
Fri, Feb 5 - Tue, Feb 9
Air Canada Logo
4:45 pm - 11:07 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 22m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
4:30 pm - 3:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
21h 15m1 stop Toronto Pearson Intl
$460Air Canada
Fri, Feb 5 - Tue, Feb 9
Air Canada Logo
4:45 pm - 11:07 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
20h 22m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:50 pm - 2:45 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
15h 55m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$460Air Canada
Fri, Jan 15 - Fri, Jan 22
American Airlines Logo
4:22 pm - 9:30 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
18h 08m1 stop Miami
American Airlines Logo
6:58 pm - 11:37 amORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
15h 39m1 stop Miami
$461American Airlines
Thu, Apr 1 - Sun, Apr 11
American Airlines Logo
5:33 pm - 7:25 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 52m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
5:00 am - 2:26 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
7h 26m1 stop Miami
$462American Airlines
Fri, Nov 6 - Mon, Nov 9
American Airlines Logo
5:33 pm - 7:25 amSXM  Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl
15h 52m2 stops Miami Washington, D.C. Reagan-National
American Airlines Logo
6:00 am - 4:31 pmORD  Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana
8h 31m1 stop Miami
$462American Airlines
Fri, Nov 6 - Mon, Nov 9

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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
Dec 1
SXM2:52 pmSimpson Bay Princess Juliana
18h 53m
1 stop
ORD7:45 amChicago O'Hare Intl
Dec 8
ORD7:54 pmChicago O'Hare Intl
15h 56m
1 stop
SXM1:50 pmSimpson Bay Princess Juliana
$583
United Airlines
Dec 16
SXM2:52 pmSimpson Bay Princess Juliana
19h 00m
1 stop
ORD7:52 amChicago O'Hare Intl
Dec 22
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM3:57 pmSimpson Bay Princess Juliana
$608
United Airlines
Dec 16
SXM2:52 pmSimpson Bay Princess Juliana
19h 00m
1 stop
ORD7:52 amChicago O'Hare Intl
Dec 23
ORD8:40 amChicago O'Hare Intl
5h 17m
SXM3:57 pmSimpson Bay Princess Juliana
$670

American Airlines flights from St. Maarten to Chicago

Our best American Airlines deals on St. Maarten to Chicago flight tickets
American Airlines
Nov 6
SXM5:33 pmSimpson Bay Princess Juliana
9h 11m
1 stop
ORD12:44 amChicago O'Hare Intl
Nov 9
ORD6:00 amChicago O'Hare Intl
8h 31m
1 stop
SXM4:31 pmSimpson Bay Princess Juliana
$457
American Airlines
Apr 1
SXM4:22 pmSimpson Bay Princess Juliana
18h 08m
1 stop
ORD9:30 amChicago O'Hare Intl
Apr 11
ORD6:58 pmChicago O'Hare Intl
15h 39m
1 stop
SXM11:37 amSimpson Bay Princess Juliana
$461
American Airlines
Nov 6
SXM5:33 pmSimpson Bay Princess Juliana
15h 52m
2 stops
ORD7:25 amChicago O'Hare Intl
Nov 9
ORD6:00 amChicago O'Hare Intl
8h 31m
1 stop
SXM4:31 pmSimpson Bay Princess Juliana
$462

momondo Fare Finder

 
Use the filters below to find and compare flights from St. Maarten to Chicago that are best for you.

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Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 1/15

4:45 pm-9:08 am

1 stop18h 23m

Chicago O'Hare Intl

Fri 1/22

1:55 pm-2:45 pm

1 stop22h 50m

$449

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 1/15

4:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Fri 1/22

1:55 pm-2:45 pm

1 stop22h 50m

$452
Quickest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-12:44 am

1 stop9h 11m

Chicago O'Hare Intl

Mon 11/9

6:00 am-4:31 pm

1 stop8h 31m

$457

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

3:26 pm-11:56 pm

1 stop10h 30m

Chicago O'Hare Intl

Mon 11/9

6:00 am-4:31 pm

1 stop8h 31m

$457

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 2/5

4:45 pm-9:08 am

1 stop18h 23m

Chicago O'Hare Intl

Tue 2/9

8:50 pm-3:45 pm

1 stop16h 55m

$457

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 2/5

4:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Tue 2/9

4:30 pm-3:45 pm

1 stop21h 15m

$460

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 1/15

4:45 pm-11:07 am

2 stops20h 22m

Chicago O'Hare Intl

Fri 1/22

8:50 pm-2:45 pm

2 stops15h 55m

$460

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Thu 4/1

4:22 pm-9:30 am

1 stop18h 08m

Chicago O'Hare Intl

Sun 4/11

6:58 pm-11:37 am

1 stop15h 39m

$461

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-7:25 am

2 stops15h 52m

Chicago O'Hare Intl

Mon 11/9

5:00 am-2:26 pm

1 stop7h 26m

$462

Simpson BayChicago

SXM Simpson Bay Princess Juliana - ORD Chicago O'Hare Intl

SXMORD

Simpson Bay Princess Juliana

Fri 11/6

5:33 pm-7:25 am

2 stops15h 52m

Chicago O'Hare Intl

Mon 11/9

6:00 am-4:31 pm

1 stop8h 31m

$462

Flights are sorted by cheapest round-trip flights 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 31% 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

Best Price Found

$238

Fastest flight time

6h 01m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from St. Maarten in the past 72 hours is $238. The best round-trip flight deal from St. Maarten to Chicago found on momondo in the last 72 hours is $449.
The fastest flight from St. Maarten to Chicago takes 6h 01m
Direct flights go from St. Maarten to Chicago on Monday, Tuesday, Thursday, Friday, Saturday 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
Saint Joseph
Benton Harbor
Lansing
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

Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport