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$105+ 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 10/17. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Oct 22 — Oct 291
Wed 10/22
Wed 10/29
1 adult, Economy
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Cheap flight deals from Stewart to Wisconsin

Keep the following information in mind while searching for Stewart to Wisconsin flight deals. Data was last updated September 22, 2025.

Round-trip from

$220
(Kiwi.com)

One-way from

$105
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$363
From New Windsor Stewart to Wisconsin
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One-way flight from New Windsor Stewart to Wisconsin
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Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 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 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 September 22, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/1711:31 amSWF - ORD
1 stop24h 19mMultiple Airlines
Sun 10/197:43 pmORD - SWF
1 stop13h 28mMultiple Airlines
Deal found 9/20$220
This Mytrip deal was found by Cheapflights users on 9/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/3111:31 amSWF - ORD
1 stop14h 32mMultiple Airlines
Thu 11/65:59 pmORD - SWF
1 stop15h 42mMultiple Airlines
Deal found 9/21$221
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Fri 10/2411:31 amSWF - ORD
1 stop13h 14mMultiple Airlines
Mon 10/275:05 amORD - SWF
1 stop8h 06mMultiple Airlines
Deal found 9/21$226
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/312:11 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Sun 10/55:05 amORD - SWF
1 stop28h 06mMultiple Airlines
Deal found 9/20$228
This Mytrip deal was found by Cheapflights users on 9/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:41 amSWF - ORD
1 stop13h 04mMultiple Airlines
Thu 10/164:59 pmORD - SWF
1 stop16h 42mMultiple Airlines
Deal found 9/22$267
This Mytrip deal was found by Cheapflights users on 9/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1011:41 amSWF - ORD
1 stop13h 04mMultiple Airlines
Sun 10/124:59 pmORD - SWF
1 stop16h 12mMultiple Airlines
Deal found 9/22$293
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Thu 11/66:14 pmSWF - ATW
1 stop22h 32mAllegiant Air
Mon 11/105:39 pmATW - SWF
1 stop15h 47mAllegiant Air
Deal found 9/21$368
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/178:21 pmSWF - ATW
1 stop20h 44mAllegiant Air
Mon 10/206:01 pmATW - SWF
1 stop15h 25mAllegiant Air
Deal found 9/20$375
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Fri 10/108:21 pmSWF - ATW
1 stop20h 44mAllegiant Air
Mon 10/206:01 pmATW - SWF
1 stop15h 25mAllegiant Air
Deal found 9/21$413
This Mytrip deal was found by Cheapflights users on 9/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/2612:17 pmSWF - MSP
1 stop9h 36mMultiple Airlines
Sat 11/296:06 pmMSP - SWF
1 stop14h 16mMultiple Airlines
Deal found 9/21$502
This Kiwi.com deal was found by Cheapflights users on 9/21. 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.
Thu 10/97:11 pmSWF - ATW
1 stop24h 40mAllegiant Air
Mon 10/206:01 pmATW - SWF
1 stop15h 25mAllegiant Air
Deal found 9/21$511
This Kiwi.com deal was found by Cheapflights users on 9/20. 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 11/267:25 pmSWF - ATW
1 stop20h 49mAllegiant Air
Sun 11/309:00 amATW - SWF
1 stop23h 06mAllegiant Air
Deal found 9/20$515

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 September 22, 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 10/17

11:31 am-10:50 am

1 stop24h 19m

Chicago O'Hare Intl

Sun 10/19

7:43 pm-10:11 am

1 stop13h 28m

$220

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/24

11:31 am-11:45 pm

1 stop13h 14m

Chicago O'Hare Intl

Mon 10/27

5:05 am-2:11 pm

1 stop8h 06m

$226

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/3

12:11 pm-10:52 am

1 stop23h 41m

Chicago O'Hare Intl

Sun 10/5

5:05 am-10:11 am

1 stop28h 06m

$228

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/10

11:41 am-11:45 pm

1 stop13h 04m

Chicago O'Hare Intl

Thu 10/16

4:59 pm-10:41 am

1 stop16h 42m

$267

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 10/10

11:41 am-6:38 pm

1 stop7h 57m

Chicago O'Hare Intl

Sun 10/12

7:43 pm-10:11 am

1 stop13h 28m

$309

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Thu 11/6

6:14 pm-3:46 pm

1 stop22h 32m

Appleton Intl

Mon 11/10

5:39 pm-10:26 am

1 stop15h 47m

$368

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Fri 10/17

8:21 pm-4:05 pm

1 stop20h 44m

Appleton Intl

Mon 10/20

6:01 pm-10:26 am

1 stop15h 25m

$375

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/21

11:12 am-6:23 pm

1 stop8h 11m

Chicago O'Hare Intl

Sun 11/23

4:01 pm-10:07 am

2 stops17h 06m

$380

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Fri 10/10

8:21 pm-4:05 pm

1 stop20h 44m

Appleton Intl

Mon 10/20

6:01 pm-10:26 am

1 stop15h 25m

$413

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 10/23

11:43 am-9:33 pm

1 stop10h 50m

Chicago O'Hare Intl

Sat 10/25

7:43 pm-11:03 am

1 stop14h 20m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/20

Showing 1-10 of 51 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, February is the cheapest month in which you can book a flight from New Windsor to Wisconsin (average of $280). Flying from New Windsor to Wisconsin 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

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 22h 32m. 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 - Appleton Intl, 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, February is the cheapest month in which you can book a flight from New Windsor to Wisconsin (average of $280). Flying from New Windsor to Wisconsin 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.

See more FAQs

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