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$131+ Cheap flights from New Windsor (SWF) 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MDW
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap flight deals from Stewart to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) 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 17, 2025.

Round-trip from

$328
(Kiwi.com)

One-way from

$131
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$213
From New Windsor Stewart to Chicago Midway
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One-way flight from New Windsor Stewart to Chicago Midway
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Highest demand for flights based on searches. 6% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Stewart to Midway

Cheapest flights from Stewart to Midway
Explore the most affordable flight options available from Stewart to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Thu 10/27:11 pmSWF - MDW
1 stop18h 33mMultiple Airlines
Sun 10/56:21 amMDW - SWF
1 stop11h 00mMultiple Airlines
Deal found 9/16$328
This Mytrip deal was found by Cheapflights users on 9/16. 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.
Thu 10/27:11 pmSWF - MDW
2 stops22h 23mAllegiant Air
Mon 10/612:08 pmMDW - SWF
2 stops21h 18mAllegiant Air
Deal found 9/16$477

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart 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 17, 2025.
Use the filters below to find and compare flights from New Windsor to Chicago Midway Airport that are best for you.

Fly from

Stewart

Fly to

Midway

Route

Depart

Return

Price

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/2

7:11 pm-12:44 pm

1 stop18h 33m

Chicago Midway

Sun 10/5

6:21 am-6:21 pm

1 stop11h 00m

$328

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/2

7:11 pm-4:34 pm

2 stops22h 23m

Chicago Midway

Mon 10/6

12:08 pm-10:26 am

2 stops21h 18m

$477

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Fri 10/17

11:31 am-11:46 pm

2 stops13h 15m

$131

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 10/5

7:11 pm-12:41 pm

1 stop18h 30m

$159

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 9/28

11:43 am-7:23 am

1 stop20h 40m

$161

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Fri 10/10

11:41 am-5:13 pm

2 stops30h 32m

$170

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/2

7:11 pm-12:44 pm

1 stop18h 33m

$172

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 10/9

11:43 am-11:46 pm

2 stops13h 03m

$191

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Best time to book a flight from Stewart to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Stewart 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 New Windsor to Chicago Midway Airport

What is the cheapest month to book a flight from New Windsor to Chicago Midway Airport?

Currently, April is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $160). Flying from New Windsor 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.

Related info for your journey

Find useful and relevant information for your journey from Stewart 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 New Windsor to Chicago Midway?

    For a flight from New Windsor to Chicago Midway, you will be flying from Stewart. New Windsor Stewart (SWF) is just 4.3 mi from the center of the city. Stewart is the only New Windsor airport and it handles 0 outbound flights to Chicago Midway per day. 0 airlines have flights to Chicago Midway from New Windsor Stewart on a regular basis.

  • How long is the flight from New Windsor to Chicago Midway Airport?

    Departing from New Windsor to Chicago Midway Airport will take you 22h 23m. The distance between New Windsor and Chicago Midway Airport is about 704 mi.

  • Can I find deals for flights from Stewart to Midway that include hotel bookings?

    Yes. In addition to deals on Stewart to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Stewart to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Midway.

  • Can I find deals for business class flights from Stewart to Midway?

    Yes. Cheapflights offers flight deals from Stewart 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 New Windsor to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $160). Flying from New Windsor 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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