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Cheap flights from Chicago Midway Airport to Simpson Bay from $213

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Simpson Bay departing on 4/27. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Chicago Midway Airport to Simpson Bay

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 7:35 am
SXM
-
MDW
18h 10m
2 stops
$520Southwest
Sun, Apr 26 - Tue, Apr 28
Southwest Logo
5:05 am - 2:25 pm
MDW
-
SXM
8h 20m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$570Southwest
Sun, May 3 - Fri, May 29
Southwest Logo
8:55 pm - 1:30 pm
MDW
-
SXM
15h 35m
2 stops
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$575Southwest
Sun, May 3 - Fri, May 29
Southwest Logo
5:15 am - 1:40 pm
MDW
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$590Southwest
Sat, May 2 - Thu, May 7
Southwest Logo
6:00 am - 1:30 pm
MDW
-
SXM
6h 30m
1 stop
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$620Southwest
Wed, May 13 - Wed, May 20
Southwest Logo
5:15 am - 1:40 pm
MDW
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 12:15 am
SXM
-
MDW
10h 50m
1 stop
$622Southwest
Sat, May 2 - Thu, May 7
Southwest Logo
5:15 am - 1:40 pm
MDW
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 7:10 am
SXM
-
MDW
17h 45m
2 stops
$627Southwest
Sat, May 2 - Thu, May 7
Southwest Logo
8:50 pm - 2:00 pm
MDW
-
SXM
16h 10m
2 stops
Southwest Logo
2:25 pm - 7:15 am
SXM
-
MDW
17h 50m
2 stops
$630Southwest
Mon, Jul 27 - Fri, Jul 31
Southwest Logo
5:20 am - 3:30 pm
MDW
-
SXM
9h 10m
1 stop
Southwest Logo
2:25 pm - 12:40 am
SXM
-
MDW
11h 15m
1 stop
$645Southwest
Sun, Jul 5 - Fri, Jul 10
Southwest Logo
9:05 pm - 2:00 pm
MDW
-
SXM
15h 55m
2 stops
Southwest Logo
3:00 pm - 10:00 pm
SXM
-
MDW
8h 00m
1 stop
$650Southwest
Tue, Jun 23 - Tue, Jun 30

Southwest flights from Chicago Midway Airport to Simpson Bay

Our best Southwest deals on Chicago Midway Airport to Simpson Bay flight tickets
Southwest
Apr 26
MDW8:55 pmChicago Midway
15h 35m
2 stops
SXM1:30 pmSimpson Bay Princess Juliana
Apr 28
SXM2:25 pmSimpson Bay Princess Juliana
18h 10m
2 stops
MDW7:35 amChicago Midway
$520
Southwest
May 3
MDW5:05 amChicago Midway
8h 20m
1 stop
SXM2:25 pmSimpson Bay Princess Juliana
May 29
SXM2:25 pmSimpson Bay Princess Juliana
10h 50m
1 stop
MDW12:15 amChicago Midway
$570
Southwest
May 3
MDW8:55 pmChicago Midway
15h 35m
2 stops
SXM1:30 pmSimpson Bay Princess Juliana
May 29
SXM2:25 pmSimpson Bay Princess Juliana
10h 50m
1 stop
MDW12:15 amChicago Midway
$575

Delta flights from Chicago Midway Airport to Simpson Bay

Our best Delta deals on Chicago Midway Airport to Simpson Bay flight tickets
Delta
May 24
MDW6:36 pmChicago Midway
18h 15m
2 stops
SXM1:51 pmSimpson Bay Princess Juliana
Jun 3
SXM3:20 pmSimpson Bay Princess Juliana
18h 23m
2 stops
MDW8:43 amChicago Midway
$670
Delta
May 3
MDW6:00 amChicago Midway
7h 05m
1 stop
SXM2:05 pmSimpson Bay Princess Juliana
May 30
SXM3:35 pmSimpson Bay Princess Juliana
21h 21m
2 stops
MDW11:56 amChicago Midway
$681
Delta
Jul 2
MDW6:05 amChicago Midway
6h 48m
1 stop
SXM1:53 pmSimpson Bay Princess Juliana
Jul 9
SXM3:18 pmSimpson Bay Princess Juliana
7h 57m
1 stop
MDW10:15 pmChicago Midway
$690

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Simpson Bay that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 5, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to Simpson Bay that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 4/26

8:55 pm-1:30 pm

2 stops15h 35m

Simpson Bay Princess Juliana

Tue 4/28

2:25 pm-7:35 am

2 stops18h 10m

$520

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 5/3

5:05 am-2:25 pm

1 stop8h 20m

Simpson Bay Princess Juliana

Fri 5/29

2:25 pm-12:15 am

1 stop10h 50m

$570

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 5/3

8:55 pm-1:30 pm

2 stops15h 35m

Simpson Bay Princess Juliana

Fri 5/29

2:25 pm-12:15 am

1 stop10h 50m

$575
Quickest round-trip

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 5/2

5:15 am-1:40 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 5/7

2:25 pm-12:15 am

1 stop10h 50m

$590

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 5/13

6:00 am-1:30 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Wed 5/20

2:25 pm-7:10 am

2 stops17h 45m

$620

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 5/2

5:15 am-1:40 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 5/7

2:25 pm-12:15 am

1 stop10h 50m

$622

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 5/2

5:15 am-1:40 pm

1 stop7h 25m

Simpson Bay Princess Juliana

Thu 5/7

2:25 pm-7:10 am

2 stops17h 45m

$627

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 7/27

8:50 pm-2:00 pm

2 stops16h 10m

Simpson Bay Princess Juliana

Fri 7/31

2:25 pm-7:15 am

2 stops17h 50m

$630

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 7/5

5:20 am-3:30 pm

1 stop9h 10m

Simpson Bay Princess Juliana

Fri 7/10

2:25 pm-12:40 am

1 stop11h 15m

$645

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 6/23

9:05 pm-2:00 pm

2 stops15h 55m

Simpson Bay Princess Juliana

Tue 6/30

3:00 pm-10:00 pm

1 stop8h 00m

$650

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Simpson Bay from

How to get the cheapest flight ticket from Chicago Midway Airport to Simpson Bay

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 day to depart on your flight to Simpson Bay?

Our data shows that Sunday is the least expensive day to fly to Simpson Bay. Tickets to fly out on this day can be as low as $617. Flights from Chicago Midway Airport to Simpson Bay on a Saturday will generally be more expensive and average around $795. Keep in mind that these prices on both days could fluctuate depending on the season and the demand.

When to book flights from Chicago Midway Airport to Simpson Bay

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

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

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

Fastest flight time

6h 48m

Direct flights

None
The fastest flight from Chicago Midway Airport to Simpson Bay takes 6h 48m
There are no direct flights from Chicago Midway Airport to Simpson Bay. There are no popular flight routes from Chicago Midway Airport to Simpson Bay.
Search flight deals

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

  • How far is Chicago Midway to Simpson Bay Princess Juliana by plane?

    Simpson Bay Princess Juliana is 2188.7 mi away from Chicago Midway. Typically, this will take 6h 48m by plane in normal conditions.

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

    Prices for flights from Chicago Midway Airport to Simpson Bay Princess Juliana Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Chicago Midway Airport to Simpson Bay Princess Juliana Airport?

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

  • What documentation or ID do you need to fly to Simpson Bay Princess Juliana Airport?

    The necessary travel and health documents for your Simpson Bay Princess Juliana 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.

  • What is the most popular airline from Chicago Midway Airport to Simpson Bay?

Best airlines flying from Chicago Midway Airport to Simpson Bay

Compare and see reviews for airlines that fly from Chicago Midway Airport to Simpson Bay with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $512Free CancellationRating
7.9
8,387 reviews
Search Delta flights

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Philipsburg

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Simpson Bay?

It is quick and easy to find Chicago to Simpson Bay flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Simpson Bay that suits you.

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

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

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

Once all potential Chicago to Simpson Bay flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

If you are not ready to book a flight from Chicago to Simpson Bay now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Simpson Bay and let you know when they change.

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