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Stewart

$217+ 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 1/286:56 pm
MKE
-
SWF
1 stop15h 37m
Multiple Airlines
Thu 2/511:48 am
SWF
-
MKE
2 stops23h 10m
Multiple Airlines
Deal found 1/24$564
This Kiwi.com deal was found by Cheapflights users on 1/23. 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.
Wed 3/186:35 pm
MKE
-
SWF
1 stop15h 33m
Multiple Airlines
Sun 3/2211:48 am
SWF
-
MKE
1 stop9h 18m
Multiple Airlines
Deal found 1/23$653
This Kiwi.com deal was found by Cheapflights users on 1/24. 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.
Wed 1/286:56 pm
MKE
-
SWF
1 stop15h 37m
Multiple Airlines
Fri 1/3011:09 am
SWF
-
MKE
2 stops32h 44m
Multiple Airlines
Deal found 1/24$690
This Kiwi.com deal was found by Cheapflights users on 1/24. 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 3/269:01 pm
MKE
-
SWF
2 stops13h 30m
Multiple Airlines
Sun 3/2911:48 am
SWF
-
MKE
1 stop9h 18m
Multiple Airlines
Deal found 1/24$1,081

Find 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 January 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$1,081
(Kiwi.com)

One-way from

$217
(Kiwi.com)

Popular in

November

Cheapest in

January

Average price

$329
Provider with most accurate pricing for Milwaukee-Mitchell-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-New Windsor Stewart flights.
Search Deals
From Milwaukee-Mitchell to New Windsor Stewart
Search Deals
One-way flight from Milwaukee-Mitchell to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 26, 2026.
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

Wed 3/18

6:35 pm-11:08 am

1 stop15h 33m

New Windsor Stewart

Sun 3/22

11:48 am-8:06 pm

1 stop9h 18m

$653

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 3/26

9:01 pm-11:31 am

2 stops13h 30m

New Windsor Stewart

Sun 3/29

11:48 am-8:06 pm

1 stop9h 18m

$1,081

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Wed 2/18

4:39 pm-11:08 am

1 stop17h 29m

$217

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 2/15

6:37 pm-10:14 am

1 stop14h 37m

$219

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Wed 2/11

4:39 pm-11:08 am

1 stop17h 29m

$231

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Wed 2/4

6:56 pm-11:08 am

1 stop15h 12m

$267

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 2/5

7:13 pm-6:43 pm

1 stop22h 30m

$271

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sat 1/31

7:48 pm-11:33 am

1 stop14h 45m

$390

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/26

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 January.
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, January is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $37). Flying from Milwaukee to New Windsor in July is currently the most expensive (average of $103). 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, January is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $37). Flying from Milwaukee to New Windsor in July is currently the most expensive (average of $103). 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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