HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Stewart

$89+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 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.
Mon 12/298:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Thu 1/111:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 12/22$675
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 12/316:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Fri 1/28:18 pmSWF - MSN
1 stop13h 50mMultiple Airlines
Deal found 12/22$685
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.
Mon 12/228:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Mon 12/2912:52 pmSWF - MKE
1 stop30h 34mMultiple Airlines
Deal found 12/21$730
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.
Sat 12/277:48 pmMKE - SWF
1 stop14h 15mMultiple Airlines
Tue 12/3011:43 amSWF - MKE
1 stop8h 37mMultiple Airlines
Deal found 12/21$757
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.
Sun 12/288:15 pmMKE - SWF
2 stops14h 29mMultiple Airlines
Sun 1/411:43 amSWF - MKE
1 stop8h 38mMultiple Airlines
Deal found 12/21$764
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.
Sat 12/276:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Fri 1/28:18 pmSWF - MSN
1 stop13h 50mMultiple Airlines
Deal found 12/22$931
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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Thu 1/111:43 amSWF - ORD
1 stop8h 19mMultiple Airlines
Deal found 12/21$972
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.
Sat 12/276:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Tue 12/304:50 pmSWF - MSN
1 stop17h 18mMultiple Airlines
Deal found 12/22$1,049
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.
Sat 12/278:42 pmMSP - SWF
2 stops13h 21mMultiple Airlines
Tue 12/3011:43 amSWF - MSP
1 stop28h 17mMultiple Airlines
Deal found 12/20$1,055
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.
Mon 12/292:18 pmMSP - SWF
1 stop19h 45mMultiple Airlines
Fri 1/212:24 pmSWF - MSP
2 stops11h 05mMultiple Airlines
Deal found 12/21$1,082
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.
Sun 12/288:09 pmORD - SWF
2 stops14h 35mMultiple Airlines
Sun 1/411:43 amSWF - ORD
1 stop8h 16mMultiple Airlines
Deal found 12/21$1,166
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.
Mon 12/228:15 pmMKE - SWF
1 stop13h 48mMultiple Airlines
Sun 12/2811:43 amSWF - MKE
1 stop8h 38mMultiple Airlines
Deal found 12/21$1,407

Find flight deals from Wisconsin to Stewart

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

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$189
(Kiwi.com)

One-way from

$89
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$439
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.
Search Deals
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. 3% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 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 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 December 23, 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 1/22

2:52 pm-10:19 am

1 stop18h 27m

New Windsor Stewart

Mon 1/26

11:09 am-11:22 am

1 stop25h 13m

$189

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Mon 1/19

11:09 am-11:47 am

2 stops25h 38m

$197

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 2/5

8:43 pm-10:19 am

1 stop12h 36m

New Windsor Stewart

Thu 2/12

11:42 am-9:13 pm

1 stop10h 31m

$267

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Fri 2/6

6:24 am-6:43 pm

1 stop11h 19m

New Windsor Stewart

Mon 2/9

11:09 am-10:59 pm

2 stops12h 50m

$391

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 1/15

8:51 pm-11:31 am

2 stops13h 40m

New Windsor Stewart

Fri 1/16

7:33 pm-2:39 pm

1 stop20h 06m

$404

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sun 1/11

8:27 pm-11:31 am

2 stops14h 04m

New Windsor Stewart

Sun 1/18

12:13 pm-7:51 pm

1 stop8h 38m

$542

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Sun 2/1

6:00 pm-11:31 am

2 stops16h 31m

New Windsor Stewart

Thu 2/5

11:48 am-7:27 pm

1 stop8h 39m

$575

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Sat 2/21

1:30 pm-11:08 am

2 stops20h 38m

New Windsor Stewart

Thu 2/26

11:48 am-7:32 pm

1 stop8h 44m

$585

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Mon 3/9

7:18 am-6:46 pm

1 stop10h 28m

New Windsor Stewart

Sun 3/15

8:40 pm-1:42 pm

1 stop18h 02m

$663

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Thu 2/19

5:18 pm-11:31 am

2 stops17h 13m

New Windsor Stewart

Sun 2/22

11:48 am-11:54 pm

1 stop13h 06m

$828

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 40 results
1
2
3
4

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 September is currently the most expensive (average of $228). 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.

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

    The most popular route from Wisconsin to New Windsor is Chicago O'Hare Intl - New Windsor Stewart. You may also consider Milwaukee-Mitchell - New Windsor Stewart or Minneapolis St Paul - 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 September is currently the most expensive (average of $228). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Stewart

See prices for flight routes from nearby airports that may be better suited for you.
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to John F Kennedy Intl flights
O'Hare Intl to John F Kennedy Intl flights
Dallas/Fort Worth to Newark flights
San Francisco to John F Kennedy Intl flights
Los Angeles to Newark flights
Fort Lauderdale to John F Kennedy Intl flights
Atlanta to John F Kennedy Intl flights
Los Angeles to LaGuardia flights
Hobby to LaGuardia flights
Miami to John F Kennedy Intl flights
Atlanta to LaGuardia flights
Orlando to John F Kennedy Intl flights
Miami to LaGuardia flights
Fort Lauderdale to LaGuardia flights
Fort Lauderdale to Newark flights
San Francisco to Newark flights
Seattle to John F Kennedy Intl flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Newark flights
Hobby to John F Kennedy Intl flights
Orlando to Newark flights
Hobby to Newark flights
Miami to Newark flights
Orlando to LaGuardia flights
Tampa to LaGuardia flights
West Palm Beach to Newark flights
San Francisco to LaGuardia flights
Atlanta to Newark flights
George Bush Intcntl to Newark flights
George Bush Intcntl to LaGuardia flights
Seattle to Newark flights
Austin to John F Kennedy Intl flights
George Bush Intcntl to John F Kennedy Intl flights
Tampa to John F Kennedy Intl flights
Charlotte to John F Kennedy Intl flights
Sky Harbor Intl to John F Kennedy Intl flights
Tampa to Newark flights
Denver to LaGuardia flights
West Palm Beach to John F Kennedy Intl flights
San Diego to John F Kennedy Intl flights
Minneapolis to LaGuardia flights
Raleigh to LaGuardia flights
West Palm Beach to LaGuardia flights
Raleigh to John F Kennedy Intl flights
Ontario to John F Kennedy Intl flights
Seattle to LaGuardia flights
Denver to John F Kennedy Intl flights
Charlotte to LaGuardia flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.