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Stewart

$151+ Cheap flights from Milwaukee to New Windsor (MKE - 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 12/14. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
1 adult, Economy
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Cheap flight deals from Milwaukee to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) 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 octubre 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$517
(Kiwi.com)

One-way from

$151
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$368
Provider with most accurate pricing for Milwaukee-Mitchell-New Windsor Stewart flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-New Windsor Stewart flights.
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From Milwaukee-Mitchell to New Windsor Stewart
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One-way flight from Milwaukee-Mitchell to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Milwaukee to Stewart

Cheapest flights from Milwaukee to Stewart
Explore the most affordable flight options available from Milwaukee to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/26. 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. 12/188:15 pmMKE - SWF
1 stop22h 06mMultiple Airlines
sáb. 12/209:45 amSWF - MKE
1 stop10h 35mMultiple Airlines
Deal found 10/26$517
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
mar. 12/238:15 pmMKE - SWF
1 stop19h 29mMultiple Airlines
mar. 12/3011:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 10/27$553
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
vie. 12/198:15 pmMKE - SWF
1 stop11h 40mMultiple Airlines
dom. 12/2111:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 10/27$643
This Kiwi.com deal was found by Cheapflights users on 10/27. 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. 12/188:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
dom. 12/2111:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 10/27$864
This Kiwi.com deal was found by Cheapflights users on 10/26. 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. 12/258:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
dom. 1/411:43 amSWF - MKE
1 stop12h 31mMultiple Airlines
Deal found 10/26$900
This Kiwi.com deal was found by Cheapflights users on 10/26. 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. 12/258:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
dom. 12/2811:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 10/26$1,018

Cheapflights Fare Finder

 
Customize your flight search to find flights from Milwaukee 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 octubre 28, 2025.
Use the filters below to find and compare flights from Milwaukee to New Windsor that are best for you.

Fly from

Milwaukee

Fly to

Stewart

Route

Depart

Return

Price

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

jue. 12/18

8:15 pm-7:21 pm

1 stop22h 06m

New Windsor Stewart

sáb. 12/20

9:45 am-7:20 pm

1 stop10h 35m

$517

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

mar. 12/23

8:15 pm-4:44 pm

1 stop19h 29m

New Windsor Stewart

mar. 12/30

11:43 am-7:20 pm

1 stop8h 37m

$553

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

vie. 12/19

8:15 pm-8:55 am

1 stop11h 40m

New Windsor Stewart

dom. 12/21

11:43 am-7:20 pm

1 stop8h 37m

$643

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

jue. 12/18

8:15 pm-11:44 am

2 stops14h 29m

New Windsor Stewart

dom. 12/21

11:43 am-7:20 pm

1 stop8h 37m

$864

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

jue. 12/25

8:15 pm-11:44 am

2 stops14h 29m

New Windsor Stewart

dom. 1/4

11:43 am-11:14 pm

1 stop12h 31m

$889

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

jue. 12/25

8:15 pm-11:44 am

2 stops14h 29m

New Windsor Stewart

dom. 12/28

11:43 am-7:20 pm

1 stop8h 37m

$1,018

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

dom. 12/14

10:34 am-11:37 am

2 stops24h 03m

$151

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

jue. 11/13

7:03 pm-11:44 am

2 stops15h 41m

$191

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

dom. 11/2

7:03 pm-11:44 am

2 stops15h 41m

$255

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

vie. 12/5

10:34 am-10:19 am

3 stops46h 45m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 14 results
1
2

Compare providers for flights from Milwaukee 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 Milwaukee to Stewart in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 Milwaukee-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-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 Milwaukee-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 Milwaukee to Stewart

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

What is the cheapest month to book a flight from Milwaukee to New Windsor?

Currently, November is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $50). Flying from Milwaukee to New Windsor in July is currently the most expensive (average of $104). 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 Milwaukee to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee 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 Milwaukee to New Windsor?

    Currently, November is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $50). Flying from Milwaukee to New Windsor in July is currently the most expensive (average of $104). 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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