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$255+ 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 2/22. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
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 January 28, 2026.

This Delta deal was found by Cheapflights users on 1/27. 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 2/141:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Sat 2/216:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 1/27$576
This Delta deal was found by Cheapflights users on 1/26. 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 2/121:38 pm
SXM
-
MDW
1 stop10h 53m
Delta
Sun 2/156:00 am
MDW
-
SXM
1 stop6h 50m
Delta
Deal found 1/26$786
This Delta deal was found by Cheapflights users on 1/27. 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 3/1312:55 pm
SXM
-
MDW
1 stop10h 36m
Delta
Sat 3/216:00 am
MDW
-
SXM
1 stop8h 08m
Delta
Deal found 1/27$1,432
This WestJet deal was found by Cheapflights users on 1/27. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/133:20 pm
SXM
-
MDW
2 stops46h 09m
WestJet
Sat 3/212:05 pm
MDW
-
SXM
2 stops23h 12m
WestJet
Deal found 1/27$3,244

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 January 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$576
(Delta)

One-way from

$255
(Kiwi.com)
Provider with most accurate pricing for Simpson Bay Princess Juliana-Chicago (CHI) flight deals.
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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 January 28, 2026.
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 2/14

1:38 pm-10:31 pm

1 stop10h 53m

Chicago Midway

Sat 2/21

6:00 am-2:50 pm

1 stop6h 50m

$576

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 2/12

1:38 pm-10:31 pm

1 stop10h 53m

Chicago Midway

Sun 2/15

6:00 am-2:50 pm

1 stop6h 50m

$786

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/13

12:55 pm-10:31 pm

1 stop10h 36m

Chicago Midway

Sat 3/21

6:00 am-3:08 pm

1 stop8h 08m

$1,432

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Fri 3/13

3:20 pm-12:29 pm

2 stops46h 09m

Chicago Midway

Sat 3/21

2:05 pm-2:17 pm

2 stops23h 12m

$3,244

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 2/22

3:20 pm-7:47 pm

2 stops30h 27m

$255

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Tue 4/7

2:14 pm-8:07 pm

2 stops30h 53m

$260

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Thu 4/9

2:14 pm-11:13 pm

2 stops33h 59m

$261

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 4/13

2:14 pm-1:00 pm

2 stops23h 46m

$262

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Sun 4/12

2:14 pm-8:07 pm

2 stops30h 53m

$274

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

Mon 4/6

2:14 pm-8:07 pm

2 stops30h 53m

$293

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 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 53m. 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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