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.

$256 Cheap Flights from St. Maarten to Chicago Midway Airport in 2026

1 adult

0 bags

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

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.

2:25 pm - 7:10 am

SXM

MDW

17h 45m

2 stops

8:50 pm - 1:30 pm

MDW

SXM

15h 40m

2 stops

$522Southwest

Wed, May 6 - Wed, May 13

2:25 pm - 12:05 am

SXM

MDW

10h 40m

1 stop

5:05 am - 2:25 pm

MDW

SXM

8h 20m

1 stop

$539Southwest

Thu, Apr 23 - Sun, May 3

2:25 pm - 7:10 am

SXM

MDW

17h 45m

2 stops

8:55 pm - 1:30 pm

MDW

SXM

15h 35m

2 stops

$544Southwest

Thu, Apr 23 - Sun, May 3

2:25 pm - 7:10 am

SXM

MDW

17h 45m

2 stops

6:00 am - 1:30 pm

MDW

SXM

6h 30m

1 stop

$566Southwest

Wed, May 6 - Wed, May 13

3:20 pm - 11:40 pm

SXM

MDW

9h 20m

1 stop

5:05 am - 2:25 pm

MDW

SXM

8h 20m

1 stop

$581Southwest

Sun, Apr 19 - Sun, Apr 26

1:35 pm - 10:28 pm

SXM

MDW

9h 53m

1 stop

6:00 am - 2:05 pm

MDW

SXM

7h 05m

1 stop

$625Delta

Fri, Apr 17 - Tue, Apr 28

3:30 pm - 4:26 pm

SXM

MDW

25h 56m

2 stops

12:52 pm - 12:10 pm

MDW

SXM

22h 18m

2 stops

$630Delta

Fri, Apr 17 - Mon, Apr 27

1:35 pm - 10:28 pm

SXM

MDW

9h 53m

1 stop

6:00 am - 2:05 pm

MDW

SXM

7h 05m

1 stop

$650Delta

Fri, Apr 17 - Sat, Apr 25

3:21 pm - 12:30 pm

SXM

MDW

22h 09m

2 stops

5:59 pm - 1:56 pm

MDW

SXM

18h 57m

2 stops

$655Delta

Wed, Aug 12 - Sat, Aug 29

1:35 pm - 10:28 pm

SXM

MDW

9h 53m

1 stop

6:00 am - 2:05 pm

MDW

SXM

7h 05m

1 stop

$666Delta

Sat, Apr 18 - Sat, Apr 25

WestJet flights from St. Maarten to Chicago Midway Airport

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

WestJet

May 14

SXM2:40 pmSimpson Bay Princess Juliana

19h 03m

3 stops

MDW8:43 amChicago Midway

May 20

MDW6:36 pmChicago Midway

18h 14m

3 stops

SXM1:50 pmSimpson Bay Princess Juliana

$1,229

WestJet

Apr 21

SXM3:20 pmSimpson Bay Princess Juliana

27h 38m

2 stops

MDW5:58 pmChicago Midway

Apr 25

MDW7:16 pmChicago Midway

41h 34m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

$3,154

WestJet

Apr 17

SXM3:20 pmSimpson Bay Princess Juliana

27h 38m

2 stops

MDW5:58 pmChicago Midway

Apr 24

MDW7:16 pmChicago Midway

41h 34m

2 stops

SXM1:50 pmSimpson Bay Princess Juliana

$3,252

Southwest flights from St. Maarten to Chicago Midway Airport

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

Southwest

May 6

SXM2:25 pmSimpson Bay Princess Juliana

17h 45m

2 stops

MDW7:10 amChicago Midway

May 13

MDW8:50 pmChicago Midway

15h 40m

2 stops

SXM1:30 pmSimpson Bay Princess Juliana

$522

Southwest

May 6

SXM2:25 pmSimpson Bay Princess Juliana

17h 45m

2 stops

MDW7:10 amChicago Midway

May 13

MDW6:00 amChicago Midway

6h 30m

1 stop

SXM1:30 pmSimpson Bay Princess Juliana

$566

Southwest

Apr 19

SXM3:20 pmSimpson Bay Princess Juliana

9h 20m

1 stop

MDW11:40 pmChicago Midway

Apr 26

MDW5:05 amChicago Midway

8h 20m

1 stop

SXM2:25 pmSimpson Bay Princess Juliana

$581

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

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 5/6

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Wed 5/13

8:50 pm-1:30 pm

2 stops15h 40m

$522

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:25 pm-12:05 am

1 stop10h 40m

Chicago Midway

Sun 5/3

5:05 am-2:25 pm

1 stop8h 20m

$539

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/23

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Sun 5/3

8:55 pm-1:30 pm

2 stops15h 35m

$544

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 5/6

2:25 pm-7:10 am

2 stops17h 45m

Chicago Midway

Wed 5/13

6:00 am-1:30 pm

1 stop6h 30m

$566

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 4/19

3:20 pm-11:40 pm

1 stop9h 20m

Chicago Midway

Sun 4/26

5:05 am-2:25 pm

1 stop8h 20m

$581

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/17

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Tue 4/28

6:00 am-2:05 pm

1 stop7h 05m

$625

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/17

3:30 pm-4:26 pm

2 stops25h 56m

Chicago Midway

Mon 4/27

12:52 pm-12:10 pm

2 stops22h 18m

$630

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/17

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Sat 4/25

6:00 am-2:05 pm

1 stop7h 05m

$650

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 8/12

3:21 pm-12:30 pm

2 stops22h 09m

Chicago Midway

Sat 8/29

5:59 pm-1:56 pm

2 stops18h 57m

$655

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 4/18

1:35 pm-10:28 pm

1 stop9h 53m

Chicago Midway

Sat 4/25

6:00 am-2:05 pm

1 stop7h 05m

$666

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 is the most popular carrier 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

Fastest flight time	17h 45m
Direct flights	None

The fastest flight from St. Maarten to Chicago Midway Airport takes 17h 45m

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

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.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

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.