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Simpson Bay

$219+ Cheap flights from Midway (MDW) to Simpson Bay (SXM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Midway to Simpson Bay

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Simpson Bay (SXM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 17, 2025.

Round-trip from

$365
(Frontier)

One-way from

$219
(Cheapflightsfares)

Popular in

December

Cheapest in

August

Average price

$612
From Chicago Midway to Simpson Bay Princess Juliana
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One-way flight from Chicago Midway to Simpson Bay Princess Juliana
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Highest demand for flights based on searches. 8% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Midway to Simpson Bay

Cheapest flights from Midway to Simpson Bay
Explore the most affordable flight options available from Midway to Simpson Bay. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Mytrip deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/279:20 amMDW - SXM
2 stops28h 01mWestJet
Fri 10/313:20 pmSXM - MDW
2 stops22h 48mWestJet
Deal found 9/16$639
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/196:00 amMDW - SXM
1 stop6h 55mDelta
Sun 11/234:20 pmSXM - MDW
1 stop9h 12mDelta
Deal found 9/15$757
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Wed 11/54:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$762
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/186:00 amMDW - SXM
1 stop6h 49mDelta
Sat 10/253:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$787
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/511:00 amMDW - SXM
1 stop26h 21mMultiple Airlines
Tue 11/114:20 pmSXM - MDW
2 stops42h 52mMultiple Airlines
Deal found 9/15$811
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/316:00 amMDW - SXM
1 stop6h 49mDelta
Fri 11/74:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$857
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:00 amMDW - SXM
1 stop6h 49mDelta
Sat 11/13:14 pmSXM - MDW
1 stop8h 00mDelta
Deal found 9/15$897
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/296:00 amMDW - SXM
1 stop6h 55mDelta
Sat 12/63:25 pmSXM - MDW
1 stop10h 07mDelta
Deal found 9/14$922
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - SXM
2 stops11h 52mMultiple Airlines
Mon 12/294:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 9/15$928

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway 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, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Simpson Bay that are best for you.

Fly from

Midway

Fly to

Simpson Bay

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 10/27

9:20 am-2:21 pm

2 stops28h 01m

Simpson Bay Princess Juliana

Fri 10/31

3:20 pm-1:08 pm

2 stops22h 48m

$639

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/19

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sun 11/23

4:20 pm-11:32 pm

1 stop9h 12m

$757

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 11/1

6:00 am-1:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Wed 11/5

4:14 pm-10:14 pm

1 stop8h 00m

$762

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 10/18

6:00 am-1:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Sat 10/25

3:14 pm-10:14 pm

1 stop8h 00m

$787

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 11/5

11:00 am-3:21 pm

1 stop26h 21m

Simpson Bay Princess Juliana

Tue 11/11

4:20 pm-10:05 am

1 stop19h 45m

$817

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 11/6

6:00 am-2:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Thu 11/13

4:20 pm-11:32 pm

1 stop9h 12m

$857

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 11/29

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Sat 12/6

3:25 pm-11:32 pm

1 stop10h 07m

$922

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 11/8

6:00 am-2:49 pm

1 stop6h 49m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-11:32 pm

1 stop9h 12m

$942

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 9/30

1:08 pm-1:50 pm

2 stops23h 42m

Simpson Bay Princess Juliana

Sun 10/12

3:14 pm-10:14 pm

1 stop8h 00m

$947

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 10/3

6:00 am-1:50 pm

1 stop6h 50m

Simpson Bay Princess Juliana

Wed 10/8

3:14 pm-10:14 pm

1 stop8h 00m

$987

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 12 results
1
2

Best time to book a flight from Midway to Simpson Bay

Have a flexible travel schedule? Discover the best time to fly to Simpson Bay from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Reviews of airlines servicing Simpson Bay

Get insights into the airlines that provide service to Simpson Bay. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Simpson Bay. Reviews last updated September 17, 2025.
See what other customers who have flown with Delta from Chicago Midway Airport to Simpson Bay have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Crew

8.5

Food

7.3

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Midway to Simpson Bay. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Simpson Bay from Chicago Midway?

    Located just 0.5 mi from the city center, Simpson Bay Princess Juliana is the airport most travelers will use when flying to Simpson Bay from Chicago Midway. Booking flights from Chicago Midway to Princess Juliana (SXM) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 1 airline.

  • How long is the flight from Chicago Midway Airport to Simpson Bay?

    WestJet and Delta can get you from Chicago Midway Airport to Simpson Bay in just under 6h 55m. Your travel time can differ by up to 21h 06m. The distance between Chicago Midway Airport and Simpson Bay is about 2189 mi. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Simpson Bay that include hotel bookings?

    Yes. In addition to deals on Midway to Simpson Bay flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Simpson Bay?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Simpson Bay.

  • Can I find deals for business class flights from Midway to Simpson Bay?

    Yes. Cheapflights offers flight deals from Midway to Simpson Bay by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Simpson Bay?

    Currently, September is the cheapest month in which you can book a flight from Chicago Midway Airport to Simpson Bay (average of $459). Flying from Chicago Midway Airport to Simpson Bay in March is currently the most expensive (average of $652). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Simpson Bay?

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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Midway to Simpson Bay

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Simpson Bay flights

Top airline flying from Midway to Simpson Bay

Discover the top airline that operate flights from Midway to Simpson Bay. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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