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$388+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
SXM — MDW
ago. 3 — ago. 101
dom. 8/3
dom. 8/10
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 julio 29, 2025.

Round-trip from

$828
(Delta)

One-way from

$388
(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 julio 29, 2025.

This Delta deal was found by Cheapflights users on 7/28. 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.
sáb. 8/303:21 pmSXM - MDW
1 stop25h 02mDelta
sáb. 9/66:00 amMDW - SXM
1 stop6h 56mDelta
Deal found 7/28$828
This Mytrip deal was found by Cheapflights users on 7/28. 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.
sáb. 8/166:10 pmSXM - MDW
3 stops24h 27mMultiple Airlines
sáb. 8/231:43 pmMDW - SXM
2 stops22h 32mMultiple Airlines
Deal found 7/28$2,089

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 julio 29, 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

sáb. 8/30

3:21 pm-3:23 pm

1 stop25h 02m

Chicago Midway

sáb. 9/6

6:00 am-1:56 pm

1 stop6h 56m

$828

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 8/16

6:10 pm-5:37 pm

3 stops24h 27m

Chicago Midway

sáb. 8/23

1:43 pm-1:15 pm

2 stops22h 32m

$2,089

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

lun. 1/19

1:05 pm-10:05 am

2 stops23h 00m

$388

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

lun. 1/19

1:45 pm-9:46 pm

1 stop10h 01m

$485

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

sáb. 11/29

1:05 pm-3:20 pm

2 stops28h 15m

$576

Simpson BayChicago

SXM - MDW

SXMMDW

Simpson Bay Princess Juliana

dom. 11/30

4:20 pm-1:09 pm

2 stops22h 49m

$661

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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.

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 julio 29, 2025.
Peruse reviews from past customers who have flown with Delta, Air Transat, and WestJet from Simpson Bay to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Air Transat
7.7
Good
424 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,972 reviews
Delta
8.0
Very good
7,979 reviews

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

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 $485 on Delta. Other airlines that offer cheap prices include Air Transat from $576 and WestJet from $661 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 Chicago Midway Airport?

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

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