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Simpson Bay

$163+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Mar 31 — Apr 71
Mon 3/31
Mon 4/7
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 March 26, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$433
(Frontier)

One-way from

$163
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$839
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. 5% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 26, 2025.

This Frontier deal was found by Cheapflights users on 3/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/309:12 pmMDW - SXM
1 stop13h 12mFrontier
Sat 6/1412:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 3/25$433
This Delta deal was found by Cheapflights users on 3/25. 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 9/66:00 amMDW - SXM
1 stop6h 48mDelta
Sat 9/133:15 pmSXM - MDW
1 stop7h 32mDelta
Deal found 3/25$710
This WestJet deal was found by Cheapflights users on 3/25. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2812:51 pmMDW - SXM
2 stops48h 25mWestJet
Fri 4/43:10 pmSXM - MDW
2 stops28h 23mWestJet
Deal found 3/25$3,279

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 March 26, 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

Fri 5/30

9:12 pm-11:24 am

1 stop13h 12m

Simpson Bay Princess Juliana

Sat 6/14

12:36 pm-8:17 pm

1 stop8h 41m

$433

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 9/6

6:00 am-1:48 pm

1 stop6h 48m

Simpson Bay Princess Juliana

Sat 9/13

3:15 pm-9:47 pm

1 stop7h 32m

$710

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 4/9

7:09 pm-2:16 pm

2 stops42h 07m

Simpson Bay Princess Juliana

Tue 4/15

3:10 pm-9:07 am

2 stops42h 57m

$3,430

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 5/15

1:19 pm-2:00 pm

2 stops23h 41m

$187

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 5/15

6:00 am-1:54 pm

1 stop6h 54m

$333

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

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 March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 starsTrust Score*1 star

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-Simpson Bay flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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 March 26, 2025.
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,891 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
KLM
7.8
Good
1,318 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
WestJet
7.2
Good
2,785 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Frontier
6.0
Okay
3,272 reviews
Delta
8.0
Very good
7,891 reviews

Comfort

8.0

Crew

8.5

Boarding

8.2

Entertainment

7.9

Overall

8.0

Food

7.3

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 0 different airlines.

  • What are the cheapest airlines flying from Chicago Midway Airport to Simpson Bay round-trip?

    Our cheapest airline available from Chicago Midway Airport to Simpson Bay is Frontier. Our recent data shows that you can find tickets from as low as $433 on this airline. Additional options worth looking into are Delta and KLM, starting at $622 and $1,058 round-trip.

  • 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 July is currently the most expensive (average of $679). 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.

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