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$287+ 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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheap 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 December 14, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/14. 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 12/214:20 pmSXM - MDW
1 stop19h 45mMultiple Airlines
Sun 12/286:00 amMDW - SXM
2 stops30h 15mMultiple Airlines
Deal found 12/14$849
This Delta deal was found by Cheapflights users on 12/14. 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 12/211:45 pmSXM - MDW
1 stop10h 37mDelta
Sun 12/286:00 amMDW - SXM
1 stop6h 50mDelta
Deal found 12/14$1,274

Find 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 December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$492
(Delta)

One-way from

$287
(Delta)
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Simpson Bay Princess Juliana-Chicago (CHI) flights.
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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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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 December 14, 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

Wed 1/28

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Wed 2/4

6:00 am-2:55 pm

1 stop6h 55m

$492

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/26

1:05 pm-10:10 am

2 stops23h 05m

Chicago Midway

Mon 2/2

11:05 am-2:40 pm

3 stops25h 35m

$753

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/26

1:55 pm-10:22 pm

1 stop10h 27m

Chicago Midway

Mon 2/2

6:00 am-2:55 pm

1 stop6h 55m

$785

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Wed 1/28

1:05 pm-10:05 am

2 stops23h 00m

Chicago Midway

Wed 2/4

11:00 am-11:55 am

2 stops22h 55m

$993

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 1/22

4:20 pm-12:46 pm

2 stops22h 26m

Chicago Midway

Mon 1/26

9:33 am-3:21 pm

2 stops27h 48m

$3,186

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 1/26

4:20 pm-12:49 pm

2 stops22h 29m

Chicago Midway

Mon 2/2

1:26 pm-3:17 pm

2 stops23h 51m

$3,561

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 12/19

3:20 pm-9:04 pm

2 stops31h 44m

$344

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 3/22

11:30 am-1:41 pm

2 stops27h 11m

$381

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 4/26

3:35 pm-4:25 pm

2 stops25h 50m

$500

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sat 4/25

1:20 pm-10:15 pm

1 stop9h 55m

$555

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/12

Showing 1-10 of 15 results
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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 10h 27m. Fly via Delta or WestJet to get the fastest option. The distance between Simpson Bay and Chicago Midway Airport is about 2189 mi. This flight may include one or multiple stops.

  • 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.

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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Simpson Bay to O'Hare Intl flights

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