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Stewart

$87+ Cheap flights from Wisconsin to New Windsor (SWF)

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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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Find flight deals from Wisconsin to Stewart

Cheapest flights from Wisconsin to Stewart
Explore the most affordable flight options available from Wisconsin to Stewart. 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 11/5. 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 11/205:00 amORD - SWF
1 stop28h 22mMultiple Airlines
Mon 11/2410:57 amSWF - ORD
1 stop23h 20mMultiple Airlines
Deal found 11/5$256
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2312:32 pmORD - SWF
2 stops20h 35mMultiple Airlines
Wed 11/2612:17 pmSWF - ORD
1 stop11h 56mMultiple Airlines
Deal found 11/6$328
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.
Sat 12/134:42 pmMSP - SWF
1 stop17h 21mMultiple Airlines
Mon 12/157:30 pmSWF - MSP
1 stop19h 48mMultiple 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.
Thu 11/2012:35 pmMKE - SWF
2 stops20h 47mMultiple Airlines
Sun 11/2311:43 amSWF - MKE
1 stop8h 05mMultiple Airlines
Deal found 11/5$395
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.
Sat 12/64:40 pmMSP - SWF
1 stop17h 23mMultiple Airlines
Mon 12/87:30 pmSWF - MSP
1 stop20h 36mMultiple Airlines
Deal found 11/5$403
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/195:30 amMSP - SWF
1 stop12h 51mMultiple Airlines
Mon 12/228:25 pmSWF - MSP
2 stops18h 47mMultiple Airlines
Deal found 11/4$413
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/201:55 pmMSP - SWF
2 stops19h 27mMultiple Airlines
Mon 12/15:49 pmSWF - MSP
2 stops26h 41mMultiple Airlines
Deal found 11/4$414
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.
Wed 12/106:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Fri 5/812:11 pmSWF - MSN
2 stops30h 45mBreeze Airways
Deal found 11/5$422
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 11/2511:41 amMSP - SWF
2 stops22h 46mMultiple Airlines
Wed 11/267:25 pmSWF - MSP
1 stop19h 45mMultiple Airlines
Deal found 11/5$430
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.
Sat 12/136:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Fri 5/812:11 pmSWF - MSN
2 stops30h 45mBreeze Airways
Deal found 11/5$433
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.
Sat 11/153:24 pmMSP - SWF
1 stop18h 39mMultiple Airlines
Sun 11/166:14 pmSWF - MSP
1 stop21h 10mMultiple Airlines
Deal found 11/6$454
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 11/2511:41 amMSP - SWF
2 stops22h 46mMultiple Airlines
Sun 11/308:41 pmSWF - MSP
1 stop26h 34mMultiple Airlines
Deal found 11/5$476

Cheap flight deals from Wisconsin to Stewart

Keep the following information in mind while searching for Wisconsin to Stewart flight deals. Data was last updated November 6, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$235
(Kiwi.com)

One-way from

$87
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$379
Provider with most accurate pricing for Milwaukee-Mitchell-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-New York (NYC) flights.
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From Wisconsin to New Windsor Stewart
Search Deals
One-way flight from Wisconsin to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Stewart 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 Wisconsin to New Windsor that are best for you.

Fly from

Wisconsin

Fly to

Stewart

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/20

5:00 am-10:22 am

1 stop28h 22m

New Windsor Stewart

Mon 11/24

10:57 am-9:17 am

1 stop23h 20m

$256

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 11/13

8:28 am-10:11 am

2 stops24h 43m

New Windsor Stewart

Mon 11/17

12:01 pm-12:27 am

1 stop13h 26m

$259

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/8

7:52 pm-10:19 am

1 stop13h 27m

New Windsor Stewart

Sun 1/11

12:13 pm-7:45 pm

1 stop8h 32m

$263

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Fri 1/30

7:24 am-5:12 pm

1 stop8h 48m

New Windsor Stewart

Sun 2/1

10:48 am-10:33 pm

1 stop12h 45m

$299

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 11/23

12:32 pm-10:07 am

2 stops20h 35m

New Windsor Stewart

Wed 11/26

12:17 pm-11:13 pm

1 stop11h 56m

$328

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

7:52 pm-10:19 am

1 stop13h 27m

New Windsor Stewart

Mon 1/19

11:09 am-6:47 pm

1 stop8h 38m

$334

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Sat 12/13

4:42 pm-11:03 am

1 stop17h 21m

New Windsor Stewart

Mon 12/15

7:30 pm-2:18 pm

1 stop19h 48m

$369

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 11/20

12:35 pm-10:22 am

2 stops20h 47m

New Windsor Stewart

Sun 11/23

11:43 am-6:48 pm

1 stop8h 05m

$395

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Sat 12/6

4:40 pm-11:03 am

1 stop17h 23m

New Windsor Stewart

Mon 12/8

7:30 pm-3:06 pm

1 stop20h 36m

$403

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Fri 12/19

5:30 am-7:21 pm

1 stop12h 51m

New Windsor Stewart

Mon 12/22

8:25 pm-2:12 pm

2 stops18h 47m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 50 results
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Best time to book a flight from Wisconsin to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Wisconsin 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 Wisconsin to New Windsor

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

Currently, April is the cheapest month in which you can book a flight from Wisconsin to New Windsor (average of $83). Flying from Wisconsin to New Windsor in December is currently the most expensive (average of $230). 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 Wisconsin to Stewart. 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 into for flights to New Windsor from Wisconsin?

    Most people fly into New Windsor Stewart (SWF) if they book a flight to New Windsor from Wisconsin. Stewart is conveniently located just 4.3 mi from New Windsor’s city center.

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

    Breeze Airways can get you from Wisconsin to New Windsor in just under 15h 55m. Your travel time can differ by up to . There are 785 mi between Wisconsin and New Windsor.

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

    The most popular route from Wisconsin to New Windsor is Minneapolis St Paul - New Windsor Stewart. You may also consider Chicago O'Hare Intl - New Windsor Stewart or Milwaukee-Mitchell - New Windsor Stewart.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Wisconsin to New Windsor (average of $83). Flying from Wisconsin to New Windsor in December is currently the most expensive (average of $230). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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