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Simpson Bay

$210+ 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 2/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Jan 27 — Feb 31
Mon 1/27
Mon 2/3
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 January 22, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$576
(Frontier)

One-way from

$210
(Kiwi.com)
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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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 January 22, 2025.

This Frontier deal was found by Cheapflights users on 1/22. 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 5/302:44 pmMDW - SXM
2 stops19h 14mFrontier
Sat 6/1412:18 pmSXM - MDW
2 stops12h 37mFrontier
Deal found 1/22$576
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Wed 3/265:35 pmMDW - SXM
2 stops16h 20mMultiple Airlines
Thu 4/312:05 pmSXM - MDW
2 stops29h 35mMultiple Airlines
Deal found 1/21$613
This Delta deal was found by Cheapflights users on 1/22. 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 2/196:00 amMDW - SXM
1 stop7h 16mDelta
Tue 2/251:40 pmSXM - MDW
1 stop10h 40mDelta
Deal found 1/22$642
This Mytrip deal was found by Cheapflights users on 1/21. 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.
Wed 3/2610:25 amMDW - SXM
3 stops26h 51mWestJet
Thu 4/33:10 pmSXM - MDW
2 stops24h 07mWestJet
Deal found 1/21$791

Find flights from Midway to Simpson Bay within your budget

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 January 22, 2025.

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Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 5/30

2:44 pm-10:58 am

2 stops19h 14m

Simpson Bay Princess Juliana

Sat 6/14

12:18 pm-11:55 pm

2 stops12h 37m

$576

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/26

5:35 pm-10:55 am

2 stops16h 20m

Simpson Bay Princess Juliana

Thu 4/3

12:05 pm-4:40 pm

2 stops29h 35m

$613

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 2/22

6:00 am-4:10 pm

1 stop8h 10m

Simpson Bay Princess Juliana

Fri 2/28

1:40 pm-10:20 pm

1 stop10h 40m

$667

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 3/26

10:25 am-2:16 pm

3 stops26h 51m

Simpson Bay Princess Juliana

Thu 4/3

3:10 pm-2:17 pm

2 stops24h 07m

$791

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Fri 2/21

12:26 pm-2:30 pm

3 stops24h 04m

$210

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/23

6:00 am-3:16 pm

1 stop7h 16m

$318

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/22

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 January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 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 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 January 22, 2025.
Delta
8.0
Very good
8,512 reviews

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

Delta
8.0
Very good
8,512 reviews
Delta
8.0
Very good
8,512 reviews

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

WestJet
7.2
Good
2,829 reviews
Delta
8.0
Very good
8,512 reviews

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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

Frontier
6.1
Okay
3,441 reviews
Delta
8.0
Very good
8,512 reviews

Overall

8.0

Crew

8.6

Entertainment

7.9

Comfort

8.0

Boarding

8.2

Food

7.3

Reviews

1 / 10

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 $576 on this airline. Additional options worth looking into are Delta and WestJet, starting at $642 and $791 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 $684). 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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