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$121+ 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 3/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MDW
Mar 23 — Mar 301
Mon 3/23
Mon 3/30
1 adult, Economy
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Cheap 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 February 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Fri 3/2012:11 pm
SWF
-
MDW
2 stops9h 42m
Multiple Airlines
Fri 3/279:51 pm
MDW
-
SWF
1 stop11h 47m
Multiple Airlines
Deal found 2/18$483
This Kiwi.com deal was found by Cheapflights users on 2/18. 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 6/259:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Mon 6/297:41 pm
MDW
-
SWF
1 stop14h 27m
Multiple Airlines
Deal found 2/18$533
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 7/29:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Mon 7/67:41 pm
MDW
-
SWF
1 stop14h 27m
Multiple Airlines
Deal found 2/19$547
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 7/309:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Mon 8/37:41 pm
MDW
-
SWF
1 stop14h 27m
Multiple Airlines
Deal found 2/19$608
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 5/289:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Sun 5/317:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Deal found 2/19$630
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 6/259:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Sun 6/287:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Deal found 2/20$634
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/219:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Mon 5/257:41 pm
MDW
-
SWF
2 stops38h 44m
Multiple Airlines
Deal found 2/17$646
This Kiwi.com deal was found by Cheapflights users on 2/17. 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 5/249:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Sun 5/317:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Deal found 2/17$652

Find 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 February 21, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$483
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$216
Provider with most accurate pricing for New Windsor Stewart-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Chicago Midway flights.
Search Deals
From New Windsor Stewart to Chicago Midway
Search Deals
One-way flight from New Windsor Stewart to Chicago Midway
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

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 February 21, 2026.
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

Fri 3/20

12:11 pm-8:53 pm

2 stops9h 42m

Chicago Midway

Fri 3/27

9:51 pm-10:38 am

1 stop11h 47m

$483

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 5/21

9:38 am-6:36 pm

1 stop9h 58m

Chicago Midway

Mon 5/25

7:41 pm-11:25 am

2 stops38h 44m

$646

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Wed 5/13

12:05 pm-10:19 pm

2 stops11h 14m

$141

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Mon 3/9

12:11 pm-8:53 pm

2 stops9h 42m

$143

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 5/7

9:38 am-8:04 am

1 stop23h 26m

$148

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Fri 3/13

12:11 pm-11:51 pm

2 stops12h 40m

$149

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 4/19

11:45 am-10:19 pm

2 stops11h 34m

$151

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 4/30

11:45 am-10:19 pm

2 stops11h 34m

$152

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Fri 3/6

12:11 pm-11:51 pm

2 stops12h 40m

$152

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 3/5

11:48 am-1:08 pm

1 stop26h 20m

$155

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

Showing 1-10 of 11 results
1
2
  • Most accurate provider: When it comes to deals on New Windsor-Chicago Midway Airport flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on New Windsor-Chicago Midway Airport flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from New Windsor-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Chicago Midway Airport flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for New Windsor-Chicago Midway Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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, December is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $48). Flying from New Windsor to Chicago Midway Airport in August is currently the most expensive (average of $194). 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.

  • 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, December is the cheapest month in which you can book a flight from New Windsor to Chicago Midway Airport (average of $48). Flying from New Windsor to Chicago Midway Airport in August is currently the most expensive (average of $194). 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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