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.

$298 Cheap Flights from St. Maarten to Chicago Midway Airport in 2026

1 adult

0 bags

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 - 7:35 am

SXM

MDW

18h 10m

2 stops

9:05 pm - 2:00 pm

MDW

SXM

15h 55m

2 stops

$695Southwest

Tue, Jun 2 - Tue, Jun 9

1:20 pm - 10:35 pm

SXM

MDW

10h 15m

1 stop

4:35 pm - 12:25 pm

MDW

SXM

18h 50m

2 stops

$820Southwest

Sat, May 9 - Fri, May 15

1:20 pm - 10:35 pm

SXM

MDW

10h 15m

1 stop

9:25 pm - 12:25 pm

MDW

SXM

14h 00m

1 stop

$835Southwest

Sat, May 9 - Fri, May 15

2:25 pm - 7:35 am

SXM

MDW

18h 10m

2 stops

5:10 am - 2:00 pm

MDW

SXM

7h 50m

1 stop

$965Southwest

Tue, Jun 2 - Tue, Jun 9

1:20 pm - 10:35 pm

SXM

MDW

10h 15m

1 stop

8:10 pm - 3:30 pm

MDW

SXM

18h 20m

2 stops

$1,055Southwest

Sat, May 30 - Sat, Jun 6

1:20 pm - 10:35 pm

SXM

MDW

10h 15m

1 stop

5:15 am - 1:15 pm

MDW

SXM

7h 00m

1 stop

$1,110Southwest

Sat, May 30 - Sat, Jun 6

6:10 pm - 2:35 pm

SXM

MDW

21h 25m

2 stops

10:30 am - 9:25 am

MDW

SXM

21h 55m

2 stops

$1,205Multiple Airlines

Sat, May 9 - Fri, May 15

6:00 pm - 12:42 pm

SXM

MDW

19h 42m

2 stops

6:36 pm - 2:20 pm

MDW

SXM

18h 44m

2 stops

$1,513Multiple Airlines

Sat, May 30 - Sat, Jun 6

6:00 pm - 6:33 pm

SXM

MDW

25h 33m

3 stops

6:36 pm - 2:20 pm

MDW

SXM

18h 44m

3 stops

$1,533Multiple Airlines

Sat, May 30 - Sat, Jun 6

6:10 pm - 6:33 pm

SXM

MDW

25h 23m

3 stops

9:22 am - 9:25 am

MDW

SXM

23h 03m

3 stops

$1,593Multiple Airlines

Sat, May 9 - Fri, May 15

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Southwest flights from St. Maarten to Chicago Midway Airport

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

Southwest

Jun 2

SXM2:25 pmSimpson Bay Princess Juliana

18h 10m

2 stops

MDW7:35 amChicago Midway

Jun 9

MDW9:05 pmChicago Midway

15h 55m

2 stops

SXM2:00 pmSimpson Bay Princess Juliana

$695

Southwest

May 9

SXM1:20 pmSimpson Bay Princess Juliana

10h 15m

1 stop

MDW10:35 pmChicago Midway

May 15

MDW4:35 pmChicago Midway

18h 50m

2 stops

SXM12:25 pmSimpson Bay Princess Juliana

$820

Southwest

May 9

SXM1:20 pmSimpson Bay Princess Juliana

10h 15m

1 stop

MDW10:35 pmChicago Midway

May 15

MDW9:25 pmChicago Midway

14h 00m

1 stop

SXM12:25 pmSimpson Bay Princess Juliana

$835

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

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 6/2

2:25 pm-7:35 am

2 stops18h 10m

Chicago Midway

Tue 6/9

9:05 pm-2:00 pm

2 stops15h 55m

$695

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/9

1:20 pm-10:35 pm

1 stop10h 15m

Chicago Midway

Fri 5/15

4:35 pm-12:25 pm

2 stops18h 50m

$820

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/9

1:20 pm-10:35 pm

1 stop10h 15m

Chicago Midway

Fri 5/15

9:25 pm-12:25 pm

1 stop14h 00m

$835

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 6/2

2:25 pm-7:35 am

2 stops18h 10m

Chicago Midway

Tue 6/9

5:10 am-2:00 pm

1 stop7h 50m

$965

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/30

1:20 pm-10:35 pm

1 stop10h 15m

Chicago Midway

Sat 6/6

8:10 pm-3:30 pm

2 stops18h 20m

$1,055

Quickest round-trip

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/30

1:20 pm-10:35 pm

1 stop10h 15m

Chicago Midway

Sat 6/6

5:15 am-1:15 pm

1 stop7h 00m

$1,110

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/9

6:10 pm-2:35 pm

2 stops21h 25m

Chicago Midway

Fri 5/15

10:30 am-9:25 am

2 stops21h 55m

$1,205

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/30

6:00 pm-12:42 pm

2 stops19h 42m

Chicago Midway

Sat 6/6

6:36 pm-2:20 pm

2 stops18h 44m

$1,513

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/30

6:00 pm-6:33 pm

3 stops25h 33m

Chicago Midway

Sat 6/6

6:36 pm-2:20 pm

3 stops18h 44m

$1,533

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 5/9

6:10 pm-6:33 pm

3 stops25h 23m

Chicago Midway

Fri 5/15

9:22 am-9:25 am

3 stops23h 03m

$1,593

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

Fastest flight time	18h 10m
Direct flights	None

The fastest flight from St. Maarten to Chicago Midway Airport takes 18h 10m

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.

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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.