How old do you have to be to fly from St. Maarten to Chicago Midway Airport?

The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St. Maarten to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport 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.

$283 Cheap Flights from St. Maarten to Chicago Midway Airport in 2026

Find the cheapest flights from St. Maarten to Chicago

Round-trip

One-way

Last minute

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

Enter your travel dates to find the best prices.

3:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:04 am - 1:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 36m1 stop Atlanta Hartsfield-Jackson

$512Delta

Wed, Oct 14 - Mon, Oct 19

3:20 pm - 11:50 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

22h 30m2 stops Orlando Las Vegas Harry Reid Intl

9:05 pm - 2:20 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

15h 15m2 stops Baltimore/Washington Orlando

$588Southwest

Wed, Dec 16 - Wed, Dec 30

3:20 pm - 5:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

16h 20m2 stops Orlando Las Vegas Harry Reid Intl

9:05 pm - 3:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

16h 35m2 stops Baltimore/Washington Orlando

$616Southwest

Tue, Dec 15 - Sun, Dec 20

3:20 pm - 12:15 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 55m2 stops Orlando Nashville Intl

9:05 pm - 2:20 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

15h 15m2 stops Baltimore/Washington Orlando

$624Southwest

Wed, Dec 23 - Wed, Dec 30

4:40 pm - 11:10 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 30m1 stop Baltimore/Washington

5:25 am - 3:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

8h 15m1 stop Orlando

$786Southwest

Wed, Dec 23 - Wed, Dec 30

3:20 pm - 5:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

16h 20m2 stops Orlando Las Vegas Harry Reid Intl

5:25 am - 3:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

8h 15m1 stop Orlando

$791Southwest

Wed, Dec 16 - Wed, Dec 30

3:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:04 am - 2:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 36m1 stop Atlanta Hartsfield-Jackson

$801Delta

Sat, Oct 31 - Sat, Nov 7

4:05 pm - 10:55 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 50m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:50 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 50m1 stop Atlanta Hartsfield-Jackson

$811Delta

Wed, Dec 16 - Wed, Dec 30

3:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:04 am - 2:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 36m1 stop Atlanta Hartsfield-Jackson

$830Delta

Sat, Oct 31 - Sat, Nov 7

4:05 pm - 10:55 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 50m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:50 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 50m1 stop Atlanta Hartsfield-Jackson

$1,242Delta

Wed, Dec 16 - Mon, Dec 21

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Delta flights from St. Maarten to Chicago Midway Airport

Our best Delta deals on St. Maarten to Chicago Midway Airport flight tickets

Delta

Oct 14

SXM3:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Oct 19

MDW6:04 amChicago Midway

6h 36m

1 stop

SXM1:40 pmSimpson Bay Princess Juliana

$512

Delta

Oct 31

SXM3:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Nov 7

MDW6:04 amChicago Midway

6h 36m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

$801

Delta

Dec 16

SXM4:05 pmSimpson Bay Princess Juliana

8h 50m

1 stop

MDW10:55 pmChicago Midway

Dec 30

MDW6:00 amChicago Midway

6h 50m

1 stop

SXM2:50 pmSimpson Bay Princess Juliana

$811

Southwest flights from St. Maarten to Chicago Midway Airport

Our best Southwest deals on St. Maarten to Chicago Midway Airport flight tickets

Southwest

Dec 16

SXM3:20 pmSimpson Bay Princess Juliana

22h 30m

2 stops

MDW11:50 amChicago Midway

Dec 30

MDW9:05 pmChicago Midway

15h 15m

2 stops

SXM2:20 pmSimpson Bay Princess Juliana

$588

Southwest

Dec 15

SXM3:20 pmSimpson Bay Princess Juliana

16h 20m

2 stops

MDW5:40 amChicago Midway

Dec 20

MDW9:05 pmChicago Midway

16h 35m

2 stops

SXM3:40 pmSimpson Bay Princess Juliana

$616

Southwest

Dec 23

SXM3:20 pmSimpson Bay Princess Juliana

10h 55m

2 stops

MDW12:15 amChicago Midway

Dec 30

MDW9:05 pmChicago Midway

15h 15m

2 stops

SXM2:20 pmSimpson Bay Princess Juliana

$624

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 10/14

3:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 10/19

6:04 am-1:40 pm

1 stop6h 36m

$512

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/16

3:20 pm-11:50 am

2 stops22h 30m

Chicago Midway

Wed 12/30

9:05 pm-2:20 pm

2 stops15h 15m

$588

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Tue 12/15

3:20 pm-5:40 am

2 stops16h 20m

Chicago Midway

Sun 12/20

9:05 pm-3:40 pm

2 stops16h 35m

$616

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/23

3:20 pm-12:15 am

2 stops10h 55m

Chicago Midway

Wed 12/30

9:05 pm-2:20 pm

2 stops15h 15m

$624

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/23

4:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Wed 12/30

5:25 am-3:40 pm

1 stop8h 15m

$786

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/16

3:20 pm-5:40 am

2 stops16h 20m

Chicago Midway

Wed 12/30

5:25 am-3:40 pm

1 stop8h 15m

$791

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sat 10/31

3:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Sat 11/7

6:04 am-2:40 pm

1 stop6h 36m

$801

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/16

4:05 pm-10:55 pm

1 stop8h 50m

Chicago Midway

Wed 12/30

6:00 am-2:50 pm

1 stop6h 50m

$811

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sat 10/31

3:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Sat 11/7

6:04 am-2:40 pm

1 stop6h 36m

$830

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Wed 12/16

4:05 pm-10:55 pm

1 stop8h 50m

Chicago Midway

Mon 12/21

6:00 am-2:50 pm

1 stop6h 50m

$1,242

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 Midway Airport

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 airline that flies from St. Maarten to Chicago Midway?

Southwest and Delta are the most popular carriers operating from St. Maarten to Chicago Midway

Cheap St. Maarten to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from St. Maarten to Chicago Midway Airport

Best Price Found	$283
Fastest flight time	8h 28m
Direct flights	None

The best one-way flight to Chicago Midway Airport from St. Maarten in the past 72 hours is $283. The best round-trip flight deal from St. Maarten to Chicago Midway Airport found on momondo in the last 72 hours is $512.

The fastest flight from St. Maarten to Chicago Midway Airport takes 8h 28m

There are no direct flights from St. Maarten to Chicago Midway Airport. There are no popular flight routes from St. Maarten to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from St. Maarten to Chicago Midway Airport

When did momondo last update prices for flights from St. Maarten to Chicago Midway Airport?
Prices for flights from St. Maarten to Chicago Midway Airport refresh daily.
How old do you have to be to fly from St. Maarten to Chicago Midway Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from St. Maarten to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport 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.

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Why use momondo?

Why should I use momondo to find a flight deal from St. Maarten to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from St. Maarten to Chicago for you.

Can I find flights from St. Maarten to Chicago with flexible booking policies on momondo?

Yes. All flights to Chicago from St. Maarten on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from St. Maarten to Chicago?

momondo helps you find the best flight between St. Maarten and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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.