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Stewart

$170+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$575
(Kiwi.com)

One-way from

$170
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$299
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. 4% potential increase in price ($15 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 September 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 September 11, 2025.

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.
Wed 11/2611:57 amMKE - SWF
1 stop22h 06mMultiple Airlines
Sun 11/3011:43 amSWF - MKE
1 stop26h 08mMultiple Airlines
Deal found 9/11$781

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 September 11, 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

Wed 11/26

11:57 am-11:03 am

1 stop22h 06m

New Windsor Stewart

Sun 11/30

11:43 am-12:51 pm

1 stop26h 08m

$781

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 2/12

8:24 pm-11:32 am

1 stop14h 08m

$179

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 10/23

7:38 pm-10:41 am

2 stops14h 03m

$204

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 11/20

11:57 am-10:22 am

2 stops21h 25m

$206

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 11/9

11:57 am-11:11 am

2 stops22h 14m

$222

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Wed 12/17

1:56 pm-11:03 am

1 stop20h 07m

$228

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 12/7

10:19 am-11:37 am

2 stops24h 18m

$229

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 11/2

6:25 pm-10:26 am

3 stops39h 01m

$230

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 10/19

7:38 pm-10:26 am

2 stops37h 48m

$254

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Fri 10/10

7:38 pm-11:03 am

3 stops38h 25m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 11 results
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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, October is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $109). Flying from Milwaukee 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 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, October is the cheapest month in which you can book a flight from Milwaukee to New Windsor (average of $109). Flying from Milwaukee 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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