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$88+ Cheap flights from New Windsor (SWF) to Wisconsin

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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
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Cheap flight deals from Stewart to Wisconsin

Cheapest flights from Stewart to Wisconsin
Explore the most affordable flight options available from Stewart to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 23, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/22. 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 12/3011:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Wed 12/318:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/22$636
This Kiwi.com deal was found by Cheapflights users on 12/20. 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
Tue 12/308:15 pmMKE - SWF
1 stop19h 29mMultiple Airlines
Deal found 12/20$656
This Kiwi.com deal was found by Cheapflights users on 12/20. 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
Wed 12/318:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/20$664
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/236:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/21$703
This Kiwi.com deal was found by Cheapflights users on 12/20. 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
Tue 12/308:15 pmMKE - SWF
1 stop19h 29mMultiple Airlines
Deal found 12/20$741
This Kiwi.com deal was found by Cheapflights users on 12/20. 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
Wed 12/318:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Deal found 12/20$749
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/3011:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Thu 1/18:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
Deal found 12/21$766
This Kiwi.com deal was found by Cheapflights users on 12/20. 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
Thu 1/18:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
Deal found 12/20$810
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 - ORD
1 stop8h 19mMultiple Airlines
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/22$814
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 - ORD
1 stop21h 47mMultiple Airlines
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/22$877
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 12/236:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sat 12/275:08 pmORD - SWF
1 stop15h 51mMultiple Airlines
Deal found 12/21$888
This Kiwi.com deal was found by Cheapflights users on 12/22. 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
2 stops14h 38mMultiple Airlines
Deal found 12/22$910

Find flight deals from Stewart to Wisconsin

Keep the following information in mind while searching for Stewart to Wisconsin flight deals. Data was last updated December 23, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$175
(Mytrip)

One-way from

$88
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$558
Provider with most accurate pricing for New York (NYC)-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Milwaukee-Mitchell flights.
Search Deals
From New Windsor Stewart to Wisconsin
Search Deals
One-way flight from New Windsor Stewart to Wisconsin
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($26 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 December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Wisconsin 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 23, 2025.
Use the filters below to find and compare flights from New Windsor to Wisconsin that are best for you.

Fly from

Stewart

Fly to

Wisconsin

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-7:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 1/25

8:43 pm-10:19 am

1 stop12h 36m

$175

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/30

11:09 am-7:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 2/1

8:43 pm-10:19 am

1 stop12h 36m

$183

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 1/11

10:48 am-10:53 am

2 stops25h 05m

Chicago O'Hare Intl

Wed 1/14

10:48 am-11:33 am

1 stop23h 45m

$326

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 1/15

12:13 pm-7:41 pm

1 stop8h 28m

Chicago O'Hare Intl

Sun 1/18

8:43 pm-10:19 am

1 stop12h 36m

$368

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Fri 3/13

9:52 am-8:06 pm

1 stop11h 14m

Milwaukee-Mitchell

Sun 3/15

9:01 pm-9:02 am

1 stop11h 01m

$483

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Mon 3/23

9:47 am-7:35 pm

1 stop10h 48m

Milwaukee-Mitchell

Sat 3/28

9:01 pm-11:08 am

1 stop13h 07m

$499

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Thu 2/12

11:48 am-7:32 pm

1 stop8h 44m

Minneapolis St Paul

Sun 2/15

7:36 am-6:38 pm

1 stop10h 02m

$567

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Thu 2/12

7:28 pm-3:00 pm

1 stop20h 32m

Minneapolis St Paul

Mon 2/16

7:54 am-6:47 pm

1 stop9h 53m

$574

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Fri 3/27

9:47 am-8:06 pm

1 stop11h 19m

Milwaukee-Mitchell

Sun 3/29

9:01 pm-8:57 am

1 stop10h 56m

$699

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 1/23

11:09 am-9:03 pm

1 stop10h 54m

$88

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

Showing 1-10 of 32 results
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Best time to book a flight from Stewart to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin 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 Wisconsin

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Wisconsin (average of $55). Flying from New Windsor to Wisconsin in February is currently the most expensive (average of $232). 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 Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Windsor to Wisconsin?

    New Windsor Stewart (SWF) is the airport you will fly out of if you book a flight from New Windsor to Wisconsin. It is only a 4.3 mi journey to Stewart (SWF) from New Windsor’s city center.

  • What are the most popular routes from New Windsor to Wisconsin?

    While some choose either New Windsor Stewart - Milwaukee-Mitchell or New Windsor Stewart - Wausau Central Wisconsin, New Windsor Stewart - Chicago O'Hare Intl is the most popular route from New Windsor to Wisconsin.

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

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

  • How can I find direct flights from Stewart to Wisconsin?

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

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

    Yes. Cheapflights offers flight deals from Stewart to Wisconsin 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 Wisconsin?

    Currently, May is the cheapest month in which you can book a flight from New Windsor to Wisconsin (average of $55). Flying from New Windsor to Wisconsin in February is currently the most expensive (average of $232). 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

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See prices for flight routes from nearby airports that may be better suited for you.
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