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$84+ 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 2/2. 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 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 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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 - ORD
1 stop20h 17mMultiple Airlines
Sun 1/48:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Deal found 12/9$432
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Fri 12/198:11 pmSWF - ORD
1 stop19h 38mMultiple Airlines
Sun 1/48:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/9$440
This Kiwi.com deal was found by Cheapflights users on 12/9. 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.
Fri 12/198:11 pmSWF - MSN
1 stop22h 17mMultiple Airlines
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 12/9$464
This Booking.com deal was found by Cheapflights users on 12/9. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:27 pmSWF - ORD
1 stop8h 34mMultiple Airlines
Sun 12/141:52 pmORD - SWF
2 stops20h 45mMultiple Airlines
Deal found 12/9$468
This Mytrip deal was found by Cheapflights users on 12/9. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:27 pmSWF - ORD
1 stop12h 42mMultiple Airlines
Fri 12/197:30 amORD - SWF
1 stop9h 36mMultiple Airlines
Deal found 12/9$472
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 12/216:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sun 1/44:44 pmORD - SWF
1 stop17h 03mMultiple Airlines
Deal found 12/9$484
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/196:56 pmSWF - MSP
2 stops27h 54mMultiple Airlines
Thu 1/228:24 amMSP - SWF
2 stops24h 55mMultiple Airlines
Deal found 12/10$536
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 - MSN
2 stops46h 03mMultiple Airlines
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 12/9$538
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 - ORD
1 stop20h 17mMultiple Airlines
Sun 12/284:44 pmORD - SWF
1 stop17h 03mMultiple Airlines
Deal found 12/9$572
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 12/9. 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 12/216:28 pmSWF - ORD
2 stops25h 11mMultiple Airlines
Sun 12/288:09 pmORD - SWF
1 stop14h 53mMultiple Airlines
Deal found 12/9$598

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 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$171
(Mytrip)

One-way from

$84
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$542
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. 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 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 12, 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 1/9

11:09 am-7:38 pm

1 stop9h 29m

Chicago O'Hare Intl

Sun 1/11

8:43 pm-10:19 am

1 stop12h 36m

$171

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

5:32 pm-10:19 am

1 stop15h 47m

$172

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

$190

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

$325

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Fri 1/30

11:09 am-12:06 am

2 stops13h 57m

Minneapolis St Paul

Mon 2/2

6:24 am-6:43 pm

1 stop11h 19m

$369

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/22

8:25 pm-3:42 pm

1 stop20h 17m

Chicago O'Hare Intl

Sun 1/4

8:09 pm-11:44 am

2 stops14h 35m

$432

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Sun 12/21

6:28 pm-6:39 pm

2 stops25h 11m

Chicago O'Hare Intl

Sun 1/4

4:44 pm-10:47 am

1 stop17h 03m

$484

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 12/22

8:25 pm-3:42 pm

1 stop20h 17m

Chicago O'Hare Intl

Tue 12/30

7:01 pm-4:44 pm

1 stop20h 43m

$484

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Mon 12/22

8:25 pm-5:28 pm

2 stops46h 03m

Madison Truax Field

Wed 12/31

6:08 pm-11:03 am

1 stop15h 55m

$538

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Thu 1/1

11:43 am-11:39 pm

1 stop12h 56m

Appleton Intl

Fri 1/2

7:00 am-7:28 pm

1 stop11h 28m

$573

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

Showing 1-10 of 54 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 $231). 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.

  • How long is the flight from New Windsor to Wisconsin?

    There are many flights that can get you from New Windsor to Wisconsin in 7h 13m. Fly via Allegiant Air to get the fastest option. Airlines will cover a distance of 753 mi.

  • 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 $231). 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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