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Stewart

$116+ Cheap flights from Midway (MDW) to New Windsor (SWF)

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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
1 adult, Economy
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Cheap flight deals from Midway to Stewart

Cheapest flights from Midway to Stewart
Explore the most affordable flight options available from Midway to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/287:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Sun 5/319:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Deal found 3/9$406
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Tue 6/239:16 pm
MDW
-
SWF
2 stops13h 09m
Multiple Airlines
Thu 6/259:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Deal found 3/8$575
This Kiwi.com deal was found by Cheapflights users on 3/9. 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 3/202:41 pm
MDW
-
SWF
2 stops41h 58m
Multiple Airlines
Mon 3/237:51 pm
SWF
-
MDW
1 stop17h 23m
Multiple Airlines
Deal found 3/9$611
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 7/167:41 pm
MDW
-
SWF
2 stops14h 54m
Multiple Airlines
Sun 7/199:38 am
SWF
-
MDW
1 stop9h 58m
Multiple Airlines
Deal found 3/8$799

Find flight deals from Midway to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Stewart (SWF). 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 March 12, 2026.

Most accurate provider

Expedia
1 star

Most trusted provider

Expedia
3 stars

Round-trip from

$406
(Kiwi.com)

One-way from

$116
(Kiwi.com)

Popular in

March

Cheapest in

January

Average price

$243
Provider with most accurate pricing for Chicago Midway-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-New Windsor Stewart flights.
Search Deals
From Chicago Midway to New Windsor Stewart
Search Deals
One-way flight from Chicago Midway to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Stewart 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 March 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 5/28

7:41 pm-8:51 am

1 stop12h 10m

New Windsor Stewart

Sun 5/31

9:38 am-6:36 pm

1 stop9h 58m

$414

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 3/20

2:41 pm-9:39 am

2 stops41h 58m

New Windsor Stewart

Mon 3/23

7:51 pm-12:14 pm

1 stop17h 23m

$611
Cheapest one-way

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 4/8

2:56 pm-10:55 am

2 stops18h 59m

$171

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 6/10

9:16 pm-8:49 am

2 stops34h 33m

$173

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sat 5/9

6:00 am-8:58 am

2 stops25h 58m

$173

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 5/17

2:20 pm-10:55 am

2 stops19h 35m

$175

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 5/29

7:41 pm-11:25 am

2 stops14h 44m

$178

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 5/3

8:39 am-10:50 am

1 stop25h 11m

$179

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Tue 5/5

12:27 pm-11:25 am

3 stops21h 58m

$185
Quickest one-way

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 5/24

7:41 pm-8:51 am

1 stop12h 10m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 13 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on Chicago Midway Airport-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Chicago Midway Airport-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Chicago Midway Airport-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-New Windsor 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 Chicago Midway Airport-New Windsor 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 Midway to Stewart

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

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

Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $57). Flying from Chicago Midway Airport to New Windsor in February is currently the most expensive (average of $232). 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 Midway to Stewart. 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 into for flights to New Windsor from Chicago Midway?

    Located just 4.3 mi from the city center, New Windsor Stewart is the airport most travelers will use when flying to New Windsor from Chicago Midway. Booking flights from Chicago Midway to Stewart (SWF) should be relatively easy as there are 0 daily inbound flights from Chicago Midway from 0 different airlines.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $57). Flying from Chicago Midway Airport to New Windsor in February is currently the most expensive (average of $232). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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