When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?

Prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport refresh daily.

How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport to Chicago Midway Airport.

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

The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

$236 Cheap Flights from Simpson Bay to Chicago Midway Airport in 2026/27

Find the cheapest flights from Simpson Bay to Chicago

Round-trip

One-way

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:05 pm - 10:54 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 49m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:49 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 49m1 stop Atlanta Hartsfield-Jackson

$626Delta

Thu, Dec 17 - Wed, Dec 23

4:05 pm - 10:54 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

8h 49m1 stop Atlanta Hartsfield-Jackson

6:00 am - 2:49 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 49m1 stop Atlanta Hartsfield-Jackson

$646Delta

Thu, Dec 17 - Wed, Dec 23

3:15 pm - 11:00 pmSXM Simpson Bay Princess Juliana-MDW Chicago Midway

9h 45m1 stop Orlando

3:15 pm - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

21h 00m2 stops Denver Intl Orlando

$692Southwest

Thu, Dec 17 - Wed, Dec 23

3:15 pm - 8:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

19h 25m2 stops Orlando Baltimore/Washington

4:10 pm - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

20h 05m2 stops Las Vegas Harry Reid Intl Orlando

$852Southwest

Sun, Nov 29 - Wed, Dec 2

3:15 pm - 8:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

19h 25m2 stops Orlando Baltimore/Washington

8:50 pm - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

15h 25m2 stops Phoenix Sky Harbor Intl Orlando

$861Southwest

Sun, Nov 29 - Thu, Dec 3

3:15 pm - 8:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

19h 25m2 stops Orlando Baltimore/Washington

5:20 am - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 55m1 stop Orlando

$865Southwest

Sun, Nov 29 - Wed, Dec 2

4:40 pm - 12:05 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

9h 25m1 stop Baltimore/Washington

4:10 pm - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

20h 05m2 stops Las Vegas Harry Reid Intl Orlando

$872Southwest

Sun, Nov 29 - Wed, Dec 2

3:15 pm - 8:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

19h 25m2 stops Orlando Baltimore/Washington

5:20 am - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 55m1 stop Orlando

$908Southwest

Sun, Nov 29 - Wed, Dec 2

4:40 pm - 12:05 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

9h 25m1 stop Baltimore/Washington

5:20 am - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 55m1 stop Orlando

$923Southwest

Sun, Nov 29 - Wed, Dec 2

3:15 pm - 12:40 amSXM Simpson Bay Princess Juliana-MDW Chicago Midway

11h 25m1 stop Orlando

5:20 am - 2:15 pmMDW Chicago Midway-SXM Simpson Bay Princess Juliana

6h 55m1 stop Orlando

$938Southwest

Sun, Nov 29 - Wed, Dec 2

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Southwest flights from Simpson Bay to Chicago Midway Airport

Our best Southwest deals on Simpson Bay to Chicago Midway Airport flight tickets

Southwest

Dec 17

SXM3:15 pmSimpson Bay Princess Juliana

11h 55m

2 stops

MDW1:10 amChicago Midway

Dec 23

MDW9:05 pmChicago Midway

15h 10m

2 stops

SXM2:15 pmSimpson Bay Princess Juliana

$692

Southwest

Nov 29

SXM3:15 pmSimpson Bay Princess Juliana

19h 25m

2 stops

MDW8:40 amChicago Midway

Dec 2

MDW4:10 pmChicago Midway

20h 05m

2 stops

SXM2:15 pmSimpson Bay Princess Juliana

$852

Southwest

Nov 29

SXM3:15 pmSimpson Bay Princess Juliana

19h 25m

2 stops

MDW8:40 amChicago Midway

Dec 3

MDW8:50 pmChicago Midway

15h 25m

2 stops

SXM2:15 pmSimpson Bay Princess Juliana

$861

Delta flights from Simpson Bay to Chicago Midway Airport

Our best Delta deals on Simpson Bay to Chicago Midway Airport flight tickets

Delta

Dec 17

SXM4:05 pmSimpson Bay Princess Juliana

8h 49m

1 stop

MDW10:54 pmChicago Midway

Dec 23

MDW6:00 amChicago Midway

6h 49m

1 stop

SXM2:49 pmSimpson Bay Princess Juliana

$626

Delta

Dec 17

SXM4:05 pmSimpson Bay Princess Juliana

8h 49m

1 stop

MDW10:54 pmChicago Midway

Dec 23

MDW6:00 amChicago Midway

6h 49m

1 stop

SXM2:49 pmSimpson Bay Princess Juliana

$646

Delta

Dec 12

SXM3:36 pmSimpson Bay Princess Juliana

9h 18m

1 stop

MDW10:54 pmChicago Midway

Dec 19

MDW6:00 amChicago Midway

7h 59m

1 stop

SXM3:59 pmSimpson Bay Princess Juliana

$1,010

momondo Fare Finder

Use the filters below to find and compare flights from Simpson Bay 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

Thu 12/17

4:05 pm-10:54 pm

1 stop8h 49m

Chicago Midway

Wed 12/23

6:00 am-2:49 pm

1 stop6h 49m

$626

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 12/17

4:05 pm-10:54 pm

1 stop8h 49m

Chicago Midway

Wed 12/23

6:00 am-2:49 pm

1 stop6h 49m

$646

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Thu 12/17

3:15 pm-11:00 pm

1 stop9h 45m

Chicago Midway

Wed 12/23

3:15 pm-2:15 pm

2 stops21h 00m

$692

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

3:15 pm-8:40 am

2 stops19h 25m

Chicago Midway

Wed 12/2

4:10 pm-2:15 pm

2 stops20h 05m

$852

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

3:15 pm-8:40 am

2 stops19h 25m

Chicago Midway

Thu 12/3

8:50 pm-2:15 pm

2 stops15h 25m

$861

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

3:15 pm-8:40 am

2 stops19h 25m

Chicago Midway

Wed 12/2

5:20 am-2:15 pm

1 stop6h 55m

$865

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

4:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

Wed 12/2

4:10 pm-2:15 pm

2 stops20h 05m

$872

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

3:15 pm-8:40 am

2 stops19h 25m

Chicago Midway

Wed 12/2

5:20 am-2:15 pm

1 stop6h 55m

$908

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

4:40 pm-12:05 am

1 stop9h 25m

Chicago Midway

Wed 12/2

5:20 am-2:15 pm

1 stop6h 55m

$923

Simpson BayChicago

SXM Simpson Bay Princess Juliana - MDW Chicago Midway

SXMMDW

Simpson Bay Princess Juliana

Sun 11/29

3:15 pm-12:40 am

1 stop11h 25m

Chicago Midway

Wed 12/2

5:20 am-2:15 pm

1 stop6h 55m

$938

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 Simpson Bay 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 Simpson Bay Princess Juliana to Chicago Midway?

Delta and Southwest are the most popular carriers operating from Simpson Bay Princess Juliana to Chicago Midway

When to book flights from Simpson Bay to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Simpson Bay to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Simpson Bay to Chicago Midway Airport (SXM to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Simpson Bay to Chicago Midway Airport

Best Price Found	$236
Fastest flight time	8h 49m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Simpson Bay in the past 72 hours is $236. The best round-trip flight deal from Simpson Bay to Chicago Midway Airport found on momondo in the last 72 hours is $626.

The fastest flight from Simpson Bay to Chicago Midway Airport takes 8h 49m

There are no direct flights from Simpson Bay to Chicago Midway Airport. There are no popular flight routes from Simpson Bay to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from Simpson Bay to Chicago Midway Airport

How far is Simpson Bay Princess Juliana to Chicago Midway by plane?
The distance between Simpson Bay Princess Juliana and Chicago Midway is about 2188.7 mi. Typically, this will take 8h 49m by plane in normal conditions.
When did momondo last update prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?
Prices for flights from Simpson Bay Princess Juliana Airport to Chicago Midway Airport refresh daily.
How old do you have to be to fly from Simpson Bay Princess Juliana Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Simpson Bay Princess Juliana Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek 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 Simpson Bay to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Simpson Bay.

Can I find flights from Simpson Bay to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Simpson Bay with this policy.

How can momondo help me find flights from Simpson Bay to Chicago?

Once you have performed a search for Simpson Bay to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Simpson Bay to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Simpson Bay and alert you when they change.