What is the cheapest airline that flies from St. Maarten to Chicago?

Air Canada, JetBlue, and Southwest are the most popular carriers operating 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.

$192 Cheap Flights from St. Maarten to Chicago in 2026

Find the cheapest flights from St. Maarten to Chicago

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One-way

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Direct

Recent round-trip flight deals from St. Maarten to Chicago

Enter your travel dates to find the best prices.

3:45 pm - 11:07 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

21h 22m1 stop Montreal Pierre Elliott Trudeau Intl

4:30 pm - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

21h 15m1 stop Toronto Pearson Intl

$307Air Canada

Thu, Nov 19 - Sun, Nov 22

3:45 pm - 11:07 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

21h 22m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 pm - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$324Air Canada

Thu, Nov 19 - Sun, Nov 22

3:45 pm - 9:23 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

19h 38m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

3:45 pm - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$332Air Canada

Thu, Nov 19 - Sun, Nov 22

2:40 pm - 3:52 pmSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

26h 12m1 stop Montreal Pierre Elliott Trudeau Intl

10:15 am - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

27h 30m1 stop Toronto Pearson Intl

$355Air Canada

Sat, Oct 31 - Sat, Nov 7

2:40 pm - 12:07 pmSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

22h 27m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 pm - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$368Air Canada

Sat, Oct 31 - Sat, Nov 7

2:40 pm - 10:23 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

20h 43m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

3:45 pm - 3:45 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

22h 00m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl

$376Air Canada

Sat, Oct 31 - Sat, Nov 7

6:00 pm - 9:00 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

16h 00m1 stop Toronto Pearson Intl

6:00 am - 2:00 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

7h 00m1 stop Fort Lauderdale

$429Multiple Airlines

Thu, Oct 1 - Mon, Oct 5

6:00 pm - 10:12 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

41h 12m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl

6:00 am - 2:00 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

7h 00m1 stop Fort Lauderdale

$434Multiple Airlines

Thu, Oct 1 - Mon, Oct 5

12:35 pm - 1:05 amSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

13h 30m1 stop Panama City Tocumen Intl

3:13 pm - 11:30 amORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

19h 17m1 stop Panama City Tocumen Intl

$447Copa Airlines

Wed, Oct 28 - Sat, Oct 31

2:10 pm - 6:11 pmSXM Simpson Bay Princess Juliana-ORD Chicago O'Hare Intl

6h 01mnonstop

8:40 am - 3:57 pmORD Chicago O'Hare Intl-SXM Simpson Bay Princess Juliana

5h 17mnonstop

$488United Airlines

Thu, Dec 17 - Mon, Dec 21

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Air Canada flights from St. Maarten to Chicago

Our best Air Canada deals on St. Maarten to Chicago flight tickets

Air Canada

Nov 19

SXM3:45 pmSimpson Bay Princess Juliana

21h 22m

1 stop

ORD11:07 amChicago O'Hare Intl

Nov 22

ORD4:30 pmChicago O'Hare Intl

21h 15m

1 stop

SXM3:45 pmSimpson Bay Princess Juliana

$307

Air Canada

Nov 19

SXM3:45 pmSimpson Bay Princess Juliana

21h 22m

1 stop

ORD11:07 amChicago O'Hare Intl

Nov 22

ORD3:45 pmChicago O'Hare Intl

22h 00m

2 stops

SXM3:45 pmSimpson Bay Princess Juliana

$324

Air Canada

Nov 19

SXM3:45 pmSimpson Bay Princess Juliana

19h 38m

2 stops

ORD9:23 amChicago O'Hare Intl

Nov 22

ORD3:45 pmChicago O'Hare Intl

22h 00m

2 stops

SXM3:45 pmSimpson Bay Princess Juliana

$332

United Airlines flights from St. Maarten to Chicago

Our best United Airlines deals on St. Maarten to Chicago flight tickets

United Airlines

Dec 17

SXM2:10 pmSimpson Bay Princess Juliana

6h 01m

ORD6:11 pmChicago O'Hare Intl

Dec 21

ORD8:40 amChicago O'Hare Intl

5h 17m

SXM3:57 pmSimpson Bay Princess Juliana

$488

United Airlines

Dec 17

SXM5:00 pmSimpson Bay Princess Juliana

9h 01m

1 stop

ORD12:01 amChicago O'Hare Intl

Dec 21

ORD8:40 amChicago O'Hare Intl

5h 17m

SXM3:57 pmSimpson Bay Princess Juliana

$499

United Airlines

Jan 16

SXM2:10 pmSimpson Bay Princess Juliana

6h 01m

ORD6:11 pmChicago O'Hare Intl

Jan 23

ORD8:40 amChicago O'Hare Intl

5h 17m

SXM3:57 pmSimpson Bay Princess Juliana

$576

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 11/19

3:45 pm-11:07 am

1 stop21h 22m

Chicago O'Hare Intl

Sun 11/22

4:30 pm-3:45 pm

1 stop21h 15m

$307

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 11/19

3:45 pm-11:07 am

1 stop21h 22m

Chicago O'Hare Intl

Sun 11/22

3:45 pm-3:45 pm

2 stops22h 00m

$324

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 11/19

3:45 pm-9:23 am

2 stops19h 38m

Chicago O'Hare Intl

Sun 11/22

3:45 pm-3:45 pm

2 stops22h 00m

$332

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-3:52 pm

1 stop26h 12m

Chicago O'Hare Intl

Sat 11/7

10:15 am-3:45 pm

1 stop27h 30m

$355

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-12:07 pm

1 stop22h 27m

Chicago O'Hare Intl

Sat 11/7

3:45 pm-3:45 pm

2 stops22h 00m

$368

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Sat 10/31

2:40 pm-10:23 am

2 stops20h 43m

Chicago O'Hare Intl

Sat 11/7

3:45 pm-3:45 pm

2 stops22h 00m

$376

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 10/1

6:00 pm-9:00 am

1 stop16h 00m

Chicago O'Hare Intl

Mon 10/5

6:00 am-2:00 pm

1 stop7h 00m

$429

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 10/1

6:00 pm-10:12 am

2 stops41h 12m

Chicago O'Hare Intl

Mon 10/5

6:00 am-2:00 pm

1 stop7h 00m

$434

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Wed 10/28

12:35 pm-1:05 am

1 stop13h 30m

Chicago O'Hare Intl

Sat 10/31

3:13 pm-11:30 am

1 stop19h 17m

$447

Quickest round-trip

Simpson BayChicago

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

SXMORD

Simpson Bay Princess Juliana

Thu 12/17

2:10 pm-6:11 pm

Nonstop6h 01m

Chicago O'Hare Intl

Mon 12/21

8:40 am-3:57 pm

Nonstop5h 17m

$488

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

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 29% 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	$192
Fastest flight time	6h 01m
Direct flights	Mon, Tue, Fri and Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from St. Maarten in the past 72 hours is $192. The best round-trip flight deal from St. Maarten to Chicago found on momondo in the last 72 hours is $307.

The fastest flight from St. Maarten to Chicago takes 6h 01m

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?
Based on momondo bookings for flights between St. Maarten and Chicago, the leading plane model is Boeing 737-700, making up 30.00% of the total bookings. Other popular models include Boeing 737 MAX 8 with 20.00%, Airbus A319 with 20.00%, and Airbus A320-100/200 with 20.00%.

Merrillville

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Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

Griffith

Saint John

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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.

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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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Cheap flights from St. Maarten to Chicago from $192

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 12/5. 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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Air Canada flights from St. Maarten to Chicago

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

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Can stopping save me money on St. Maarten to Chicago flights?

What is the cheapest airline that flies from St. Maarten to Chicago?

Cheap St. Maarten to Chicago flight deals and tips

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Frequently asked questions about flying from St. Maarten to Chicago

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Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

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