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Simpson Bay

$253+ 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 8/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 July 3, 2025.

Round-trip from

$549
(Kiwi.com)

One-way from

$253
(Travelocity)

Popular in

March

Cheapest in

September

Average price

$695
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 ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/2. 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 7/319:12 pmMDW - SXM
2 stops15h 48mMultiple Airlines
Thu 8/72:10 pmSXM - MDW
1 stop19h 35mMultiple Airlines
Deal found 7/2$549
This Delta deal was found by Cheapflights users on 7/1. 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 8/186:04 amMDW - SXM
1 stop6h 52mDelta
Wed 8/273:10 pmSXM - MDW
2 stops22h 18mDelta
Deal found 7/1$580
This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/102:00 pmMDW - SXM
2 stops23h 17mWestJet
Mon 12/154:10 pmSXM - MDW
2 stops22h 59mWestJet
Deal found 7/3$3,142

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 July 3, 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

Thu 7/31

9:12 pm-2:00 pm

2 stops15h 48m

Simpson Bay Princess Juliana

Thu 8/7

2:10 pm-8:45 am

1 stop19h 35m

$549

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 8/18

6:04 am-1:56 pm

1 stop6h 52m

Simpson Bay Princess Juliana

Wed 8/27

3:10 pm-12:28 pm

2 stops22h 18m

$580

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 12/10

2:00 pm-3:17 pm

2 stops23h 17m

Simpson Bay Princess Juliana

Mon 12/15

4:10 pm-1:09 pm

2 stops22h 59m

$3,142

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/2

9:12 pm-5:21 pm

2 stops43h 09m

$253

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 9/8

6:00 am-1:45 pm

1 stop6h 45m

$293

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sat 8/2

9:12 pm-2:00 pm

3 stops39h 48m

$325

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 12/28

5:04 pm-3:17 pm

2 stops20h 13m

$1,685

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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 July 3, 2025.
See what other customers who have flown with Delta, WestJet, and Frontier 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
7,982 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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!
WestJet
7.2
Good
2,917 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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!
Frontier
5.9
Fair
3,286 reviews
Delta
8.0
Very good
7,982 reviews

Entertainment

7.9

Crew

8.5

Food

7.3

Comfort

7.9

Boarding

8.2

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Simpson Bay one-way?

    The cheapest airlines for a one-way flight from Chicago Midway Airport to Simpson Bay are Frontier ($253), Delta ($293), and WestJet ($1,685).

  • 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 $656). 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

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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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$622Average$637FlexibilityNo cancel feeOn-timeN/A

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