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$95+ 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 1/19. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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 12/1212:27 pmSWF - ORD
1 stop23h 41mMultiple Airlines
Sun 12/143:20 pmORD - SWF
1 stop19h 17mMultiple Airlines
Deal found 11/3$206
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/2111:12 amSWF - ORD
1 stop23h 05mMultiple Airlines
Tue 11/2511:48 amORD - SWF
1 stop22h 39mMultiple Airlines
Deal found 11/6$243
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/2011:43 amSWF - ORD
1 stop20h 43mMultiple Airlines
Sun 11/235:00 amORD - SWF
1 stop28h 07mMultiple Airlines
Deal found 11/5$315
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/2011:43 amSWF - ORD
1 stop12h 23mMultiple Airlines
Mon 11/246:48 amORD - SWF
1 stop25h 05mMultiple Airlines
Deal found 11/4$331
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/1811:16 amSWF - MSN
1 stop22h 52mMultiple Airlines
Wed 11/196:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 11/5$350
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/1411:01 amSWF - ORD
1 stop14h 26mMultiple Airlines
Sun 11/1610:52 amORD - SWF
1 stop23h 19mMultiple Airlines
Deal found 11/4$365
This Mytrip deal was found by Cheapflights users on 11/5. 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 - ORD
1 stop17h 18mMultiple Airlines
Sun 12/2812:09 pmORD - SWF
2 stops21h 38mMultiple Airlines
Deal found 11/5$367
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sat 12/209:45 amSWF - MSP
1 stop13h 38mMultiple Airlines
Sat 1/246:30 amMSP - SWF
1 stop26h 28mMultiple Airlines
Deal found 11/4$368
This Kiwi.com deal was found by Cheapflights users on 11/6. 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 11/2111:12 amSWF - MSP
1 stop28h 36mMultiple Airlines
Tue 11/2511:41 amMSP - SWF
2 stops22h 46mMultiple Airlines
Deal found 11/6$369
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/2111:12 amSWF - MSP
2 stops45h 34mMultiple Airlines
Mon 11/242:30 pmMSP - SWF
1 stop17h 23mMultiple Airlines
Deal found 11/5$377
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/2011:06 amSWF - MSP
2 stops24h 35mMultiple Airlines
Mon 11/242:30 pmMSP - SWF
1 stop17h 23mMultiple Airlines
Deal found 11/5$380
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 11/2711:43 amSWF - MSN
2 stops26h 59mMultiple Airlines
Sat 12/66:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 11/4$409

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 November 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(Kiwi.com)

One-way from

$95
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$459
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.
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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. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
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 November 2025
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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 November 6, 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 12/12

12:27 pm-11:08 am

1 stop23h 41m

Chicago O'Hare Intl

Sun 12/14

3:20 pm-11:37 am

1 stop19h 17m

$206

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 11/21

11:12 am-9:17 am

1 stop23h 05m

Chicago O'Hare Intl

Tue 11/25

11:48 am-11:27 am

1 stop22h 39m

$243

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 11/20

11:43 am-7:26 am

1 stop20h 43m

Chicago O'Hare Intl

Sun 11/23

5:00 am-10:07 am

1 stop28h 07m

$315

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 11/20

11:43 am-11:06 pm

1 stop12h 23m

Chicago O'Hare Intl

Mon 11/24

6:48 am-8:53 am

1 stop25h 05m

$331

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 11/18

11:16 am-9:08 am

1 stop22h 52m

Madison Truax Field

Wed 11/19

6:08 pm-11:03 am

1 stop15h 55m

$350

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 12/19

6:56 pm-11:14 am

1 stop17h 18m

Chicago O'Hare Intl

Sun 12/28

12:09 pm-10:47 am

2 stops21h 38m

$367

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Sat 12/20

9:45 am-10:23 pm

1 stop13h 38m

Minneapolis St Paul

Sat 1/24

6:30 am-9:58 am

1 stop26h 28m

$368

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Fri 11/21

11:12 am-2:48 pm

1 stop28h 36m

Minneapolis St Paul

Tue 11/25

11:41 am-11:27 am

2 stops22h 46m

$369

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Fri 11/21

11:12 am-7:46 am

2 stops45h 34m

Minneapolis St Paul

Mon 11/24

2:30 pm-8:53 am

1 stop17h 23m

$377

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Thu 11/20

11:06 am-10:41 am

2 stops24h 35m

Minneapolis St Paul

Mon 11/24

2:30 pm-8:53 am

1 stop17h 23m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 60 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 April 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 28h 06m. Fly via Allegiant Air or Breeze Airways to get the fastest option. Airlines will cover a distance of 753 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    While some choose either New Windsor Stewart - Minneapolis St Paul 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, 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 April 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.

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