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.

$303 Cheap Flights from St. Maarten to Chicago Midway Airport in 2026/27

Find the cheapest flights from St. Maarten to Chicago

Round-trip

One-way

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

Enter your travel dates to find the best prices.

4:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 40m1 stop Atlanta Hartsfield-Jackson

$460Delta

Fri, Nov 6 - Mon, Nov 9

4:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 40m1 stop Atlanta Hartsfield-Jackson

$468Delta

Fri, Nov 6 - Mon, Nov 9

4:05 pm - 10:33 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 28m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:40 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 40m1 stop Atlanta Hartsfield-Jackson

$478Delta

Fri, Nov 6 - Mon, Nov 9

3:36 pm - 10:54 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

9h 18m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:45 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 45m1 stop Atlanta Hartsfield-Jackson

$654Delta

Sat, Dec 5 - Sat, Dec 12

3:15 pm - 1:10 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

11h 55m2 stops Orlando Houston Hobby

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

16h 35m2 stops Baltimore/Washington Orlando

$667Southwest

Fri, Dec 11 - Fri, Dec 18

3:15 pm - 1:10 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

11h 55m2 stops Orlando Dallas Love Field

9:05 pm - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

15h 10m2 stops Baltimore/Washington Orlando

$672Southwest

Thu, Dec 17 - Wed, Dec 23

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

$677Southwest

Thu, Dec 17 - Wed, Dec 23

2:55 pm - 11:55 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

11h 00m1 stop Orlando

5:20 am - 2:50 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

7h 30m1 stop Orlando

$690Southwest

Fri, Feb 12 - Sat, Feb 20

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

$700Southwest

Thu, Dec 17 - Wed, Dec 23

2:55 pm - 11:10 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

10h 15m2 stops Orlando Atlanta Hartsfield-Jackson

5:20 am - 2:50 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

7h 30m1 stop Orlando

$708Southwest

Fri, Feb 12 - Sat, Feb 20

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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

Nov 6

SXM4:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Nov 9

MDW6:00 amChicago Midway

6h 40m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

$460

Delta

Nov 6

SXM4:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Nov 9

MDW6:00 amChicago Midway

6h 40m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

$468

Delta

Nov 6

SXM4:05 pmSimpson Bay Princess Juliana

8h 28m

1 stop

MDW10:33 pmChicago Midway

Nov 9

MDW6:00 amChicago Midway

6h 40m

1 stop

SXM2:40 pmSimpson Bay Princess Juliana

$478

Southwest flights from St. Maarten to Chicago Midway Airport

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

Southwest

Dec 11

SXM3:15 pmSimpson Bay Princess Juliana

11h 55m

2 stops

MDW1:10 amChicago Midway

Dec 18

MDW9:05 pmChicago Midway

16h 35m

2 stops

SXM3:40 pmSimpson Bay Princess Juliana

$667

Southwest

Dec 17

SXM3:15 pmSimpson Bay Princess Juliana

9h 45m

1 stop

MDW11:00 pmChicago Midway

Dec 23

MDW3:15 pmChicago Midway

21h 00m

2 stops

SXM2:15 pmSimpson Bay Princess Juliana

$672

Southwest

Dec 17

SXM4:40 pmSimpson Bay Princess Juliana

8h 30m

1 stop

MDW11:10 pmChicago Midway

Dec 23

MDW5:25 amChicago Midway

8h 15m

1 stop

SXM3:40 pmSimpson Bay Princess Juliana

$677

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

Fri 11/6

4:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$460

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 11/6

4:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$468

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 11/6

4:05 pm-10:33 pm

1 stop8h 28m

Chicago Midway

Mon 11/9

6:00 am-2:40 pm

1 stop6h 40m

$478

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sat 12/5

3:36 pm-10:54 pm

1 stop9h 18m

Chicago Midway

Sat 12/12

6:00 am-2:45 pm

1 stop6h 45m

$654

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 12/11

3:15 pm-1:10 am

2 stops11h 55m

Chicago Midway

Fri 12/18

9:05 pm-3:40 pm

2 stops16h 35m

$667

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 12/17

3:15 pm-1:10 am

2 stops11h 55m

Chicago Midway

Wed 12/23

9:05 pm-2:15 pm

2 stops15h 10m

$672

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 12/17

4:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Wed 12/23

5:25 am-3:40 pm

1 stop8h 15m

$677

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 2/12

2:55 pm-11:55 pm

1 stop11h 00m

Chicago Midway

Sat 2/20

5:20 am-2:50 pm

1 stop7h 30m

$690

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 12/17

4:40 pm-11:10 pm

1 stop8h 30m

Chicago Midway

Wed 12/23

5:25 am-3:40 pm

1 stop8h 15m

$700

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Fri 2/12

2:55 pm-11:10 pm

2 stops10h 15m

Chicago Midway

Sat 2/20

5:20 am-2:50 pm

1 stop7h 30m

$708

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?

Delta and Southwest 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	$303
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 $303. The best round-trip flight deal from St. Maarten to Chicago Midway Airport found on momondo in the last 72 hours is $460.

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.