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$236+ 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 11/19. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$598
(Delta)

One-way from

$236
(Kiwi.com)
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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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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/9. 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 10/313:14 pmSXM - MDW
1 stop8h 00mDelta
Mon 11/36:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$598
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/293:14 pmSXM - MDW
1 stop8h 00mDelta
Mon 11/36:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$600
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/293:14 pmSXM - MDW
1 stop8h 00mDelta
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$757
This Delta deal was found by Cheapflights users on 9/10. 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.
Sat 10/253:14 pmSXM - MDW
1 stop8h 00mDelta
Sat 11/16:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/10$818
This Delta deal was found by Cheapflights users on 9/9. 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.
Wed 10/293:14 pmSXM - MDW
1 stop8h 00mDelta
Sun 11/25:00 amMDW - SXM
1 stop6h 49mDelta
Deal found 9/9$826
This Kiwi.com deal was found by Cheapflights users on 9/9. 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 10/263:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 11/211:00 amMDW - SXM
2 stops21h 50mMultiple Airlines
Deal found 9/9$909
This Delta deal was found by Cheapflights users on 9/9. 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.
Sun 10/263:14 pmSXM - MDW
2 stops28h 11mDelta
Sun 11/26:23 pmMDW - SXM
2 stops18h 26mDelta
Deal found 9/9$910

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 September 11, 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 10/31

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

Mon 11/3

6:00 am-2:49 pm

1 stop6h 49m

$598

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 10/31

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

Sun 11/2

6:23 pm-2:49 pm

2 stops18h 26m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 10/29

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

Sun 11/2

6:23 pm-2:49 pm

2 stops18h 26m

$600

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 10/29

3:14 pm-12:28 pm

2 stops22h 14m

Chicago Midway

Mon 11/3

6:00 am-2:49 pm

1 stop6h 49m

$612

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/6

4:26 pm-12:01 pm

2 stops21h 35m

Chicago Midway

Tue 3/10

1:00 pm-11:15 am

2 stops21h 15m

$652

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 10/29

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

Sat 11/1

6:00 am-1:49 pm

1 stop6h 49m

$757

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 10/25

3:14 pm-10:14 pm

1 stop8h 00m

Chicago Midway

Sat 11/1

6:00 am-1:49 pm

1 stop6h 49m

$818

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 10/26

3:20 pm-10:05 am

1 stop19h 45m

Chicago Midway

Sun 11/2

11:00 am-10:50 am

2 stops21h 50m

$909

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 11/18

4:20 pm-10:05 am

1 stop19h 45m

$361

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 11/18

4:20 pm-1:07 pm

2 stops22h 47m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 14 results
1
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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 8h. 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.

  • 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 Chicago Midway Airport?

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

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