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Stewart

$121+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/256:12 amMDW - SWF
2 stops27h 55mMultiple Airlines
Mon 12/2910:20 amSWF - MDW
1 stop23h 33mMultiple Airlines
Deal found 12/10$696
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Mon 12/226:12 amMDW - SWF
2 stops27h 51mMultiple Airlines
Tue 12/3011:43 amSWF - MDW
1 stop11h 15mMultiple Airlines
Deal found 12/11$727
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1810:13 amMDW - SWF
1 stop29h 25mMultiple Airlines
Fri 1/211:57 amSWF - MDW
2 stops26h 24mMultiple Airlines
Deal found 12/10$769

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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$696
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$232
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. 6% potential increase in price ($13 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 December 2025
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 December 12, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to New Windsor that are best for you.

Fly from

Midway

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 12/25

6:12 am-11:07 am

2 stops27h 55m

New Windsor Stewart

Mon 12/29

10:20 am-8:53 am

1 stop23h 33m

$696

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Mon 12/22

6:12 am-11:03 am

2 stops27h 51m

New Windsor Stewart

Tue 12/30

11:43 am-9:58 pm

1 stop11h 15m

$727

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 2/8

5:01 pm-11:31 am

3 stops17h 30m

$121

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 1/14

11:39 am-11:33 am

2 stops22h 54m

$131

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 1/21

1:20 pm-11:33 am

2 stops21h 13m

$138

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Wed 12/31

3:10 pm-11:03 am

1 stop18h 53m

$195

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 12/25

6:12 am-11:07 am

2 stops27h 55m

$202

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Thu 12/18

6:33 pm-8:55 am

2 stops37h 22m

$241

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 2/22

7:30 am-11:31 am

2 stops27h 01m

$256

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Sun 12/14

10:13 am-4:30 pm

1 stop29h 17m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 11 results
1
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Compare providers for flights from Midway to Stewart

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to Stewart in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-New Windsor flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-New Windsor flight deals on Cheapflights vs. eDreams >95% 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 eDreams the most. eDreams 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $44). Flying from Chicago Midway Airport to New Windsor in August is currently the most expensive (average of $227). 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, October is the cheapest month in which you can book a flight from Chicago Midway Airport to New Windsor (average of $44). Flying from Chicago Midway Airport to New Windsor in August is currently the most expensive (average of $227). 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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