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Midway

$284+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Find flight deals from Simpson Bay to Midway

One-way flights from Simpson Bay to Midway
Search for one-way flight options from Simpson Bay to Midway. Find affordable one-way fares based on user searches. Data last updated June 12, 2025.

This Priceline deal was found by Cheapflights users on 6/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2112:36 pmSXM - MDW
1 stop8h 41mFrontier
Deal found 6/11$284
This Mytrip deal was found by Cheapflights users on 6/11. 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 6/222:10 pmSXM - MDW
1 stop19h 35mMultiple Airlines
Deal found 6/11$357
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Sun 6/222:10 pmSXM - MDW
2 stops44h 31mWestJet
Deal found 6/11$526
This Delta deal was found by Cheapflights users on 6/11. 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 7/113:21 pmSXM - MDW
1 stop19h 24mDelta
Deal found 6/11$777

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 June 12, 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

Sat 6/21

12:36 pm-8:17 pm

1 stop8h 41m

$284

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 6/22

2:10 pm-8:45 am

1 stop19h 35m

$357

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 6/22

2:10 pm-9:41 am

2 stops44h 31m

$526

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 7/11

3:21 pm-9:45 am

1 stop19h 24m

$777

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Cheapflights Insights

Everything you need to know about your flight from Simpson Bay to Chicago Midway Airport

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 June 12, 2025.
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
7,950 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
2,868 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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
3,295 reviews
Delta
8.0
Very good
7,950 reviews

Boarding

8.2

Food

7.3

Crew

8.5

Comfort

7.9

Overall

8.0

Entertainment

7.9

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 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.

  • 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 $284 on Frontier. Other airlines that offer cheap prices include WestJet from $526 and Delta from $777 one-way.

  • 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.

  • 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 $160). Flying from Simpson Bay to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Simpson Bay?

Book flights to Simpson Bay if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Simpson Bay to Midway

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