HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Simpson Bay

$236+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SXM
Dec 25 — Jan 11
Wed 12/25
Wed 1/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Midway to Simpson Bay with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$490
(FlightHub)

One-way from

$236
(Kiwi.com)
Provider with most accurate pricing for Chicago Midway-Simpson Bay Princess Juliana flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-Simpson Bay Princess Juliana flights.
Search Deals
From Chicago Midway to Simpson Bay Princess Juliana
Search Deals
One-way flight from Chicago Midway to Simpson Bay Princess Juliana
Search Deals

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 December 20, 2024.

This Mytrip deal was found by Cheapflights users on 12/19. 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.
Sun 12/225:04 pmMDW - SXM
2 stops21h 11mMultiple Airlines
Sun 12/294:55 pmSXM - MDW
2 stops25h 45mMultiple Airlines
Deal found 12/19$1,184
This Delta deal was found by Cheapflights users on 12/19. 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 12/196:00 amMDW - SXM
1 stop7h 11mDelta
Fri 12/271:50 pmSXM - MDW
1 stop10h 16mDelta
Deal found 12/19$1,190
This Mytrip deal was found by Cheapflights users on 12/19. 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.
Sun 12/295:04 pmMDW - SXM
2 stops20h 13mWestJet
Tue 12/314:10 pmSXM - MDW
3 stops20h 58mWestJet
Deal found 12/19$1,720

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 December 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Thu 2/13

4:13 pm-5:09 pm

2 stops22h 56m

Simpson Bay Princess Juliana

Mon 2/17

6:31 pm-3:13 pm

2 stops22h 42m

$490

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/22

6:00 am-3:16 pm

1 stop7h 16m

Simpson Bay Princess Juliana

Wed 1/29

1:40 pm-10:20 pm

1 stop10h 40m

$630

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/2

7:25 am-10:50 am

2 stops25h 25m

Simpson Bay Princess Juliana

Sun 2/9

12:21 pm-12:17 am

2 stops37h 56m

$653

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Mon 2/3

1:26 pm-3:16 pm

2 stops23h 50m

Simpson Bay Princess Juliana

Mon 2/10

4:10 pm-5:43 pm

2 stops27h 33m

$741

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Sun 2/2

10:58 am-2:26 pm

2 stops25h 28m

$236

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/22

6:00 am-3:16 pm

1 stop7h 16m

$312

ChicagoSimpson Bay

MDW - SXM

MDWSXM

Chicago Midway

Wed 1/22

10:19 am-3:17 pm

2 stops26h 58m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

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 December.
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 December 20, 2024.
Peruse reviews from past customers who have flown with Delta and WestJet from Chicago to Simpson Bay to help guide your decision. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,601 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

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
8,601 reviews
Delta
8.0
Very good
8,601 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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

WestJet
7.3
Good
2,816 reviews
Delta
8.0
Very good
8,601 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

Reviews

1 / 10

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

Frontier
6.1
Okay
3,475 reviews
Delta
8.0
Very good
8,601 reviews

Crew

8.6

Entertainment

7.9

Boarding

8.2

Comfort

8.0

Food

7.3

Overall

8.0

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 $490 on this airline. Additional options worth looking into are Delta and WestJet, starting at $630 and $741 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 March is currently the most expensive (average of $690). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.