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$226+ 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 12/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/1811:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sat 12/208:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/10$580
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/245:34 pmSWF - MKE
1 stop26h 46mMultiple Airlines
Sun 12/288:06 pmMKE - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/10$581
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/245:34 pmSWF - MKE
1 stop26h 46mMultiple Airlines
Mon 12/298:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/10$602
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Mon 12/228:25 pmSWF - MKE
2 stops23h 55mMultiple Airlines
Sat 12/277:48 pmMKE - SWF
1 stop14h 15mMultiple Airlines
Deal found 12/10$621
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/245:34 pmSWF - MKE
1 stop26h 46mMultiple Airlines
Sat 12/277:48 pmMKE - SWF
1 stop14h 15mMultiple Airlines
Deal found 12/10$633
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sun 12/2111:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sat 1/37:58 pmMKE - SWF
1 stop14h 05mMultiple Airlines
Deal found 12/10$651
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sun 12/288:06 pmMKE - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/10$677
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Mon 12/298:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/10$697
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Tue 12/2311:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sat 12/277:48 pmMKE - SWF
1 stop14h 15mMultiple Airlines
Deal found 12/10$729
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/2511:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sun 12/288:06 pmMKE - SWF
1 stop14h 56mMultiple Airlines
Deal found 12/10$748
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/2511:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Mon 12/298:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/10$769
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/2511:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Sat 12/277:48 pmMKE - SWF
1 stop14h 15mMultiple Airlines
Deal found 12/10$800

Find flight deals from Stewart to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Milwaukee (MKE). 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 December 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$581
(Kiwi.com)

One-way from

$226
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$542
Provider with most accurate pricing for New Windsor Stewart-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Milwaukee-Mitchell flights.
Search Deals
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. 4% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Milwaukee 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 December 12, 2025.
Use the filters below to find and compare flights from New Windsor to Milwaukee that are best for you.

Fly from

Stewart

Fly to

Milwaukee

Route

Depart

Return

Price

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Wed 12/24

5:34 pm-7:20 pm

1 stop26h 46m

Milwaukee-Mitchell

Mon 12/29

8:15 pm-11:03 am

1 stop13h 48m

$602

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 1/1

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Sun 1/4

8:15 pm-11:44 am

2 stops14h 29m

$605

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Mon 12/22

8:25 pm-7:20 pm

2 stops23h 55m

Milwaukee-Mitchell

Sat 12/27

7:48 pm-11:03 am

1 stop14h 15m

$621

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Wed 12/24

5:34 pm-7:20 pm

1 stop26h 46m

Milwaukee-Mitchell

Sat 12/27

7:48 pm-11:03 am

1 stop14h 15m

$633

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Sun 12/21

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Sat 1/3

7:58 pm-11:03 am

1 stop14h 05m

$651

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Tue 12/23

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Sun 12/28

8:06 pm-12:02 pm

1 stop14h 56m

$677

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Tue 12/23

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Mon 12/29

8:15 pm-11:03 am

1 stop13h 48m

$697

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Tue 12/23

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Sat 12/27

7:48 pm-11:03 am

1 stop14h 15m

$729

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 12/25

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Sun 12/28

8:06 pm-12:02 pm

1 stop14h 56m

$748

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 12/25

11:43 am-7:20 pm

1 stop8h 37m

Milwaukee-Mitchell

Mon 12/29

8:15 pm-11:03 am

1 stop13h 48m

$769

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/9

Showing 1-10 of 15 results
1
2

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Milwaukee flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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, May is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $55). Flying from New Windsor to Milwaukee in July is currently the most expensive (average of $126). 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 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?

    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, May is the cheapest month in which you can book a flight from New Windsor to Milwaukee (average of $55). Flying from New Windsor to Milwaukee in July is currently the most expensive (average of $126). 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 Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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