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Simpson Bay

$181+ 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$363
(Priceline)

One-way from

$181
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$719
Provider with most accurate pricing for Chicago Midway-Simpson Bay Princess Juliana flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-Simpson Bay Princess Juliana flights.
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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 ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($24 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 12/116:00 amMDW - SXM
1 stop6h 28mDelta
Wed 12/173:53 pmSXM - MDW
1 stop9h 54mDelta
Deal found 10/28$375
This Delta deal was found by Cheapflights users on 10/27. 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 11/236:48 pmMDW - SXM
2 stops18h 07mDelta
Tue 11/254:20 pmSXM - MDW
2 stops18h 34mDelta
Deal found 10/27$380
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 11/106:00 amMDW - SXM
1 stop6h 55mDelta
Fri 11/144:20 pmSXM - MDW
1 stop9h 20mDelta
Deal found 10/28$437
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/166:00 amMDW - SXM
1 stop6h 28mDelta
Thu 1/81:55 pmSXM - MDW
1 stop10h 14mDelta
Deal found 10/29$481
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/161:14 pmMDW - SXM
2 stops23h 14mDelta
Fri 1/94:20 pmSXM - MDW
2 stops20h 14mDelta
Deal found 10/29$486
This Delta deal was found by Cheapflights users on 10/28. 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 12/136:00 amMDW - SXM
1 stop6h 50mDelta
Sat 12/201:45 pmSXM - MDW
1 stop10h 37mDelta
Deal found 10/28$506
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/161:14 pmMDW - SXM
2 stops23h 14mDelta
Sat 1/105:28 pmSXM - MDW
2 stops21h 20mDelta
Deal found 10/29$511
This Delta deal was found by Cheapflights users on 10/29. 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.
Tue 12/166:00 amMDW - SXM
1 stop6h 28mDelta
Tue 1/64:20 pmSXM - MDW
2 stops20h 14mDelta
Deal found 10/29$526
This Delta deal was found by Cheapflights users on 10/28. 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 12/56:00 amMDW - SXM
1 stop6h 28mDelta
Wed 12/103:53 pmSXM - MDW
1 stop9h 54mDelta
Deal found 10/28$536
This Delta deal was found by Cheapflights users on 10/27. 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 11/236:48 pmMDW - SXM
2 stops18h 07mDelta
Mon 12/14:20 pmSXM - MDW
2 stops27h 40mDelta
Deal found 10/27$541
This Kiwi.com deal was found by Cheapflights users on 10/30. 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.
Thu 12/117:23 pmMDW - SXM
2 stops40h 52mMultiple Airlines
Wed 12/174:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Deal found 10/30$569

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 October 30, 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

Sun 12/14

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Wed 12/24

1:45 pm-10:22 pm

1 stop10h 37m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/17

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Tue 12/23

1:45 pm-10:22 pm

1 stop10h 37m

$375

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 11/23

6:48 pm-2:55 pm

2 stops18h 07m

Simpson Bay Princess Juliana

Tue 11/25

4:20 pm-11:40 pm

1 stop9h 20m

$380

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 11/23

6:48 pm-2:55 pm

2 stops18h 07m

Simpson Bay Princess Juliana

Wed 11/26

4:20 pm-8:54 am

2 stops18h 34m

$380

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 11/10

6:00 am-2:55 pm

1 stop6h 55m

Simpson Bay Princess Juliana

Fri 11/14

4:20 pm-11:40 pm

1 stop9h 20m

$437

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 12/11

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Wed 12/17

3:53 pm-11:47 pm

1 stop9h 54m

$463

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/17

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Thu 1/8

1:55 pm-10:09 pm

1 stop10h 14m

$481

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 12/16

1:14 pm-2:28 pm

2 stops23h 14m

Simpson Bay Princess Juliana

Fri 1/9

4:20 pm-10:34 am

2 stops20h 14m

$486

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Tue 12/16

1:14 pm-2:28 pm

2 stops23h 14m

Simpson Bay Princess Juliana

Thu 1/8

1:55 pm-10:09 pm

1 stop10h 14m

$486

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/17

6:00 am-2:28 pm

1 stop6h 28m

Simpson Bay Princess Juliana

Fri 1/9

4:20 pm-10:34 am

2 stops20h 14m

$486

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 18 results
1
2

Compare providers for flights from Midway to Simpson Bay

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Simpson Bay in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-Simpson Bay flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-Simpson Bay flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-Simpson Bay flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-Simpson Bay flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-Simpson Bay flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 30, 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
7.9
Good
7,998 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Boarding

8.2

Crew

8.5

Overall

7.9

Food

7.3

Comfort

7.9

Entertainment

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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?

    Delta can get you from Chicago Midway Airport to Simpson Bay in just under 6h 28m. Your travel time can differ by up to . The distance between Chicago Midway Airport and Simpson Bay is about 2189 mi.

  • 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.

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

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Alternative routes for Midway to Simpson Bay

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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