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$395+ Cheap flights from Simpson Bay (SXM) to Midway (MDW)

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.
SXM — MDW
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Find flight deals from Simpson Bay to Midway

Best flights from Simpson Bay to Midway
Discover carefully curated flight deals from Simpson Bay to Midway that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 28, 2025.

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.
Fri 3/64:26 pmSXM - MDW
2 stops24h 59mDelta
Tue 3/105:59 pmMDW - SXM
2 stops16h 16mDelta
Deal found 10/27$592

Cheap flight deals from Simpson Bay to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Simpson Bay (SXM) to Midway (MDW). 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 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$592
(Delta)

One-way from

$395
(Delta)
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago Midway flight deals.
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Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago Midway flights.
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From Simpson Bay Princess Juliana to Chicago Midway
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One-way flight from Simpson Bay Princess Juliana to Chicago Midway
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Simpson Bay to Midway 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 28, 2025.
Use the filters below to find and compare flights from Simpson Bay to Chicago Midway Airport that are best for you.

Fly from

Simpson Bay

Fly to

Midway

Route

Depart

Return

Price

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-3:25 pm

2 stops24h 59m

Chicago Midway

Tue 3/10

5:59 pm-11:15 am

2 stops16h 16m

$592

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 12/13

3:25 pm-11:47 pm

1 stop10h 22m

$395

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 11/28

4:20 pm-11:50 am

1 stop21h 30m

$404

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/20

12:45 pm-9:46 pm

1 stop10h 01m

$452

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 4/3

3:20 pm-1:08 pm

2 stops46h 48m

$490

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 4/4

3:40 pm-11:42 pm

1 stop9h 02m

$569

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Compare providers for flights from Simpson Bay to Midway

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 Simpson Bay to Midway in October.
ProviderPrice AccuracyTrust Score*
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice 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 Simpson Bay-Chicago Midway Airport flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Simpson Bay-Chicago Midway Airport flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Simpson Bay-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Simpson Bay-Chicago Midway Airport 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 Simpson Bay-Chicago Midway Airport 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 Simpson Bay to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Simpson Bay 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.

Related info for your journey

Find useful and relevant information for your journey from Simpson Bay to Midway. 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 from for flights from Simpson Bay to Chicago Midway?

    If you book a flight to Chicago Midway from Simpson Bay, you will be flying from Princess Juliana, which is the city’s only airport. Simpson Bay Princess Juliana (SXM) is located 0.5 mi from the center of Simpson Bay. There are 0 flights from Princess Juliana to Chicago Midway per day from 0 different airlines.

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

    There are many flights that can get you from Simpson Bay to Chicago Midway Airport in 24h 59m. Fly via Delta to get the fastest option. The distance between Simpson Bay and Chicago Midway Airport is about 2189 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Simpson Bay to Midway 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 Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor

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