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).

How far in advance should I book a flight from New Windsor to Milwaukee?

To save on the cost of your flight from New Windsor to Milwaukee, book at least 60 days before your planned departure. Booking around this time can save you about 29% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $315 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $464.

What is the cheapest month to fly from New Windsor to Milwaukee?

Flights from New Windsor to Milwaukee lean towards being more expensive in December. Prices are generally better when you fly from New Windsor to Milwaukee in September, with the cheapest ticket starting at $105.

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.

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.

$250+ Flights from New Windsor to Milwaukee

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Cheap flight deals from Stewart to Milwaukee

Round-trip from	$587 (Kiwi.com)
One-way from	$250 (Kiwi.com)
Popular in	December
Cheapest in	September
Average price	$319

From New Windsor Stewart to Milwaukee-Mitchell

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

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Highest demand for flights based on searches. 3% potential increase in price ($12 potential increase over avg. RT price).

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Cheapest flight prices on average. 1% potential price decrease ($8 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 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 September 11, 2025.

Wed 12/245:34 pmSWF - MKE

1 stop28h 52mMultiple Airlines

Tue 12/307:48 pmMKE - SWF

1 stop19h 56mMultiple Airlines

Deal found 9/10

$587

Mon 12/227:10 pmSWF - MKE

1 stop18h 41mMultiple Airlines

Wed 12/311:56 pmMKE - SWF

1 stop20h 07mMultiple Airlines

Deal found 9/9

$628

Mon 12/227:10 pmSWF - MKE

1 stop18h 41mMultiple Airlines

Tue 12/301:56 pmMKE - SWF

1 stop25h 48mMultiple Airlines

Deal found 9/10

$631

Mon 12/227:10 pmSWF - MKE

1 stop18h 41mMultiple Airlines

Thu 1/11:56 pmMKE - SWF

2 stops20h 48mMultiple Airlines

Deal found 9/9

$642

Fri 12/1912:24 pmSWF - MKE

2 stops45h 43mMultiple Airlines

Wed 12/311:56 pmMKE - SWF

1 stop20h 07mMultiple Airlines

Deal found 9/8

$675

Wed 12/245:34 pmSWF - MKE

1 stop20h 17mMultiple Airlines

Sun 12/287:48 pmMKE - SWF

1 stop15h 14mMultiple Airlines

Deal found 9/10

$701

Sun 12/2111:43 amSWF - MKE

1 stop26h 08mMultiple Airlines

Sat 12/277:48 pmMKE - SWF

1 stop14h 15mMultiple Airlines

Deal found 9/9

$715

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 September 11, 2025.

Tue 11/259:33 amSWF - MKE

1 stop26h 29mMultiple Airlines

Sat 11/298:08 pmMKE - SWF

1 stop22h 43mMultiple Airlines

Deal found 9/8

$832

Wed 11/267:25 pmSWF - MKE

1 stop16h 37mMultiple Airlines

Sat 11/298:08 pmMKE - SWF

1 stop22h 43mMultiple Airlines

Deal found 9/8

$847

Mon 11/2410:57 amSWF - MKE

2 stops25h 05mMultiple Airlines

Sat 11/298:08 pmMKE - SWF

1 stop22h 43mMultiple Airlines

Deal found 9/8

$850

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 September 11, 2025.

Tue 11/259:33 amSWF - MKE

1 stop26h 29mMultiple Airlines

Deal found 9/9

$250

Mon 11/2410:57 amSWF - MKE

2 stops25h 05mMultiple Airlines

Deal found 9/9

$268

Sun 9/287:12 pmSWF - MKE

2 stops25h 07mMultiple Airlines

Deal found 9/9

$288

Thu 9/187:12 pmSWF - MKE

2 stops24h 29mMultiple Airlines

Deal found 9/9

$326

Sun 9/217:12 pmSWF - MKE

3 stops25h 07mMultiple Airlines

Deal found 9/10

$342

Sun 9/147:12 pmSWF - MKE

2 stops25h 07mMultiple Airlines

Deal found 9/9

$373

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

Tue 11/25

9:33 am-11:02 am

1 stop26h 29m

Milwaukee-Mitchell

Sat 11/29

8:08 pm-7:51 pm

1 stop22h 43m

$832

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Wed 11/26

7:25 pm-11:02 am

1 stop16h 37m

Milwaukee-Mitchell

Sat 11/29

8:08 pm-7:51 pm

1 stop22h 43m

$847

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Mon 11/24

10:57 am-11:02 am

2 stops25h 05m

Milwaukee-Mitchell

Sat 11/29

8:08 pm-7:51 pm

1 stop22h 43m

$850

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Tue 11/25

9:33 am-11:02 am

1 stop26h 29m

$250

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Mon 11/24

10:57 am-11:02 am

2 stops25h 05m

$268

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Sun 9/28

7:12 pm-7:19 pm

2 stops25h 07m

$288

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 9/18

7:12 pm-6:41 pm

2 stops24h 29m

$326

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Sun 9/21

7:12 pm-7:19 pm

3 stops25h 07m

$342

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Fri 12/19

6:56 pm-12:51 pm

2 stops18h 55m

$424

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Tue 12/23

11:43 am-12:51 pm

1 stop26h 08m

$443

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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, February is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $280). Flying from New Windsor to Milwaukee in June is currently the most expensive (average of $376). 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, February is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $280). Flying from New Windsor to Milwaukee in June is currently the most expensive (average of $376). 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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$250+ 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 11/25. 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

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find 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 September 11, 2025.

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 September 11, 2025.

Cheapflights Fare Finder

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

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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Alternative routes for Stewart to 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 September 11, 2025.