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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 11/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — SWF
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
1 adult, Economy
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Cheap 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 septiembre 11, 2025.

Round-trip from

$340
(Kiwi.com)

One-way from

$121
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$167
From Chicago Midway to New Windsor Stewart
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One-way flight from Chicago Midway to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($4 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 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 Midway to Stewart

One-way flights from Midway to Stewart
Search for one-way flight options from Midway to Stewart. Find affordable one-way fares based on user searches. Data last updated septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
dom. 11/94:33 pmMDW - SWF
1 stop25h 19mAllegiant Air
Deal found 9/10$121
This Kiwi.com deal was found by Cheapflights users on 9/10. 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.
lun. 11/106:06 pmMDW - SWF
1 stop15h 20mMultiple Airlines
Deal found 9/10$133
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
jue. 10/165:40 pmMDW - SWF
1 stop24h 51mAllegiant Air
Deal found 9/9$140
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
dom. 10/56:21 amMDW - SWF
1 stop11h 00mMultiple Airlines
Deal found 9/8$145
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
sáb. 9/2710:51 amMDW - SWF
1 stop23h 12mMultiple Airlines
Deal found 9/9$150
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
mié. 12/38:00 amMDW - SWF
2 stops25h 19mMultiple Airlines
Deal found 9/9$158
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
sáb. 9/2011:23 amMDW - SWF
2 stops22h 40mMultiple Airlines
Deal found 9/8$164
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
jue. 10/1612:30 pmMDW - SWF
2 stops21h 11mMultiple Airlines
Deal found 9/9$169
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
mié. 12/108:00 amMDW - SWF
2 stops25h 19mMultiple Airlines
Deal found 9/11$170

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 septiembre 11, 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

dom. 11/9

4:33 pm-6:52 pm

1 stop25h 19m

$125

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

lun. 11/10

6:06 pm-10:26 am

1 stop15h 20m

$133

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

dom. 10/26

5:20 am-6:21 pm

1 stop12h 01m

$150

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

sáb. 9/20

10:51 am-11:03 am

1 stop23h 12m

$151

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

dom. 10/5

6:21 am-6:21 pm

1 stop11h 00m

$155

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

jue. 10/2

4:46 pm-7:31 pm

1 stop25h 45m

$161

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

mié. 12/3

8:00 am-10:19 am

3 stops25h 19m

$173

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

dom. 10/19

5:40 pm-7:31 pm

1 stop24h 51m

$180

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

dom. 10/12

5:20 am-6:21 pm

1 stop12h 01m

$182

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

vie. 10/10

12:13 pm-11:03 am

2 stops45h 50m

$184

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 $109). Flying from Chicago Midway Airport to New Windsor in December is currently the most expensive (average of $202). 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 $109). Flying from Chicago Midway Airport to New Windsor in December is currently the most expensive (average of $202). 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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