In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

What is the cheapest time of day to fly from SWF to MKE?

When flying from New Windsor to Milwaukee, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Most trusted provider : When it comes to deals on New Windsor-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub 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 New Windsor-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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

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

How can I find direct flights from Stewart to Milwaukee?

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

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

Yes. Cheapflights offers flight deals from Stewart to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$323+ Flights from New Windsor to Milwaukee

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1. Tell us where you want to go

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2. Select your favorite providers

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Cheap flight deals from Stewart to Milwaukee

Cheapest flights from Stewart to Milwaukee
Explore the most affordable flight options available from Stewart to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

Sun 3/811:48 am

SWF

MKE

1 stop9h 18m

Multiple Airlines

Sat 3/149:01 pm

MKE

SWF

1 stop13h 07m

Multiple Airlines

Deal found 1/25

$721

Thu 3/2611:48 am

SWF

MKE

1 stop9h 18m

Multiple Airlines

Sun 3/299:01 pm

MKE

SWF

2 stops13h 30m

Multiple Airlines

Deal found 1/24

$999

Best flights from Stewart to Milwaukee
Discover carefully curated flight deals from Stewart to Milwaukee that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 26, 2026.

Sun 3/811:48 am

SWF

MKE

1 stop9h 18m

Multiple Airlines

Sat 3/149:01 pm

MKE

SWF

1 stop13h 07m

Multiple Airlines

Deal found 1/25

$721

Thu 3/2611:48 am

SWF

MKE

1 stop9h 18m

Multiple Airlines

Sun 3/299:01 pm

MKE

SWF

2 stops13h 30m

Multiple Airlines

Deal found 1/24

$999

Last-minute flights from Stewart to Milwaukee
Discover last-minute flight deals from Stewart to Milwaukee. Data last updated January 26, 2026 and is based on user searches.

Mon 1/267:33 pm

SWF

MKE

1 stop23h 25m

Multiple Airlines

Wed 1/286:56 pm

MKE

SWF

1 stop15h 37m

Multiple Airlines

Deal found 1/26

$758

One-way flights from Stewart to Milwaukee
Search for one-way flight options from Stewart to Milwaukee. Find affordable one-way fares based on user searches. Data last updated January 26, 2026.

Thu 2/1211:48 am

SWF

MKE

1 stop22h 55m

Multiple Airlines

Deal found 1/24

$323

Fri 2/1312:11 pm

SWF

MKE

2 stops31h 41m

Multiple Airlines

Deal found 1/24

$626

Find flight deals from Stewart to Milwaukee

Most accurate provider	FlightHub 3 stars
Most trusted provider	FlightHub 3 stars
Round-trip from	$721 (Kiwi.com)
One-way from	$323 (Kiwi.com)
Popular in	December
Cheapest in	April
Average price	$404

Provider with most accurate pricing for New Windsor Stewart-Milwaukee-Mitchell flight deals.

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Provider most trusted by Cheapflights users for New Windsor Stewart-Milwaukee-Mitchell flights.

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From New Windsor Stewart to Milwaukee-Mitchell

Search Deals

One-way flight from New Windsor Stewart to Milwaukee-Mitchell

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in January 2026

Search Deals

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Milwaukee that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Sun 3/8

11:48 am-8:06 pm

1 stop9h 18m

Milwaukee-Mitchell

Sat 3/14

9:01 pm-11:08 am

1 stop13h 07m

$721

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 3/26

11:48 am-8:06 pm

1 stop9h 18m

Milwaukee-Mitchell

Sun 3/29

9:01 pm-11:31 am

2 stops13h 30m

$999

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 2/12

11:48 am-9:43 am

1 stop22h 55m

$323

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Fri 2/13

12:11 pm-6:52 pm

2 stops31h 41m

$626

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

Compare providers for flights from Stewart to Milwaukee

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Milwaukee in January.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust 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 New Windsor-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Milwaukee flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on New Windsor-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub 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 New Windsor-Milwaukee 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 Stewart to Milwaukee

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

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

Currently, December is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $48). Flying from New Windsor to Milwaukee in July is currently the most expensive (average of $119). 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

Can I find deals for flights from Stewart to Milwaukee that include hotel bookings?
Yes. In addition to deals on Stewart to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Milwaukee?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Milwaukee.
Can I find deals for business class flights from Stewart to Milwaukee?
Yes. Cheapflights offers flight deals from Stewart to Milwaukee 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 New Windsor to Milwaukee?
Currently, December is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $48). Flying from New Windsor to Milwaukee in July is currently the most expensive (average of $119). 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.

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$323+ Cheap flights from New Windsor to Milwaukee (SWF - MKE)

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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Milwaukee with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Milwaukee

Cheapest flights from Stewart to MilwaukeeExplore the most affordable flight options available from Stewart to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

Explore the most affordable flight options available from Stewart to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

Find flight deals from Stewart to Milwaukee

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Windsor to Milwaukee that are best for you.

Compare providers for flights from Stewart to Milwaukee

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 Stewart to Milwaukee in January.

Best time to book a flight from Stewart to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Stewart with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New Windsor to Milwaukee

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

Related info for your journey

Find useful and relevant information for your journey from Stewart to Milwaukee. 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 Stewart to Milwaukee that include hotel bookings?

How can I find direct flights from Stewart to Milwaukee?

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

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

Traveling to a place near Milwaukee?

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Cheapest flights from Stewart to Milwaukee
Explore the most affordable flight options available from Stewart to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.