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$396+ 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 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Nov 3 — Nov 101
Sun 11/3
Sun 11/10
1 adult, Economy
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SXM - MDW
Nov 3 - Nov 10

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Find flight deals from Simpson Bay to Midway

Cheapest flights from Simpson Bay to Midway
Explore the most affordable flight options available from Simpson Bay to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 29, 2024.

This Delta deal was found by Cheapflights users on 10/28. 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 11/144:00 pmSXM - MDW
1 stop7h 46mDelta
Mon 11/186:00 amMDW - SXM
1 stop6h 35mDelta
Deal found 10/28$781
This Kissandfly.com deal was found by Cheapflights users on 10/28. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/264:00 pmSXM - MDW
1 stop7h 46mKLM
Sat 11/306:00 amMDW - SXM
1 stop6h 52mKLM
Deal found 10/28$926
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Tue 11/264:10 pmSXM - MDW
2 stops23h 25mWestJet
Sat 11/302:17 pmMDW - SXM
2 stops23h 00mWestJet
Deal found 10/28$1,698
This Mytrip deal was found by Cheapflights users on 10/28. 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.
Tue 11/264:10 pmSXM - MDW
2 stops23h 25mMultiple Airlines
Sat 11/302:17 pmMDW - SXM
3 stops23h 38mMultiple Airlines
Deal found 10/28$1,744

Find flights from Simpson Bay to Midway within your budget

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 2,539,541 searches. Data last updated October 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$781 - $1,744

Route

Depart

Return

Price

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 11/14

1 stop7h 46m

Chicago Midway

Mon 11/18

1 stop6h 35m

$781

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 11/26

1 stop7h 46m

Chicago Midway

Sat 11/30

1 stop6h 52m

$926

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 11/26

2 stops23h 25m

Chicago Midway

Sat 11/30

2 stops23h 00m

$1,698

Simpson Bay Princess JulianaChicago Midway

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 11/26

2 stops23h 25m

Chicago Midway

Sat 11/30

3 stops23h 38m

$1,744

Flights are sorted by cheapest first

Deals found on 10/28

  • 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.

Travel insights for flights from Simpson Bay to Midway

Get recent, data-driven insights about flights from Simpson Bay to Midway including ideal travel times, pricing trends, and more.

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated October 29, 2024.
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Delta
8.0
Very good
8,845 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

KLM
7.8
Good
1,351 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

WestJet
7.3
Good
2,801 reviews
Delta
8.0
Very good
8,845 reviews

Overall

8.0

Food

7.3

Crew

8.5

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Reviews

1 / 10

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • Can I find flights from Simpson Bay to Chicago Midway Airport for under $800 on Cheapflights?

    Yes, there are multiple flights from Simpson Bay to Chicago Midway Airport for under $800. The cheapest flight booked recently is on Delta for just $781, but on average you can expect to pay $1,287.

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

    One-way options have recently been found by users for as low as $428 on Delta. Other airlines that offer cheap prices include KLM from $490 and WestJet from $1,987 one-way.

  • What does SXM to MDW mean?

    SXM and MDW are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. SXM to MDW refers to a flight route from Simpson Bay Princess Juliana Airport to Chicago Midway Airport.

  • Can I find deals for flights from Simpson Bay to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Simpson Bay to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Simpson Bay to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Simpson Bay to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Simpson Bay to Midway that allow pets onboard?

    Many airlines flying from Simpson Bay to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Simpson Bay to Midway?

    Yes, you can often find last-minute deals on Simpson Bay to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Simpson Bay to Chicago Midway Airport flight deals updated?

    The Simpson Bay to Chicago Midway Airport flight deals you see on this page were last updated on 10/28.

  • What is the cheapest month to book a flight from Simpson Bay to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Simpson Bay to Chicago Midway Airport (average of $159). Flying from Simpson Bay to Chicago Midway Airport in July is currently the most expensive (average of $231). 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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