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$88+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Mar 7 — Mar 141
Sat 3/7
Sat 3/14
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 February 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Mon 2/911:09 am
SWF
-
ORD
1 stop25h 13m
Multiple Airlines
Sun 2/151:17 pm
ORD
-
SWF
2 stops21h 14m
Multiple Airlines
Deal found 2/4$388
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 2/185:46 pm
SWF
-
ORD
1 stop18h 00m
Multiple Airlines
Thu 2/193:40 pm
ORD
-
SWF
2 stops17h 34m
Multiple Airlines
Deal found 2/2$391
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 5/1411:45 am
SWF
-
ORD
1 stop9h 03m
Multiple Airlines
Mon 5/187:35 pm
ORD
-
SWF
2 stops38h 50m
Multiple Airlines
Deal found 2/3$394
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Sun 5/179:38 am
SWF
-
MSN
2 stops23h 47m
Multiple Airlines
Fri 5/226:50 pm
MSN
-
SWF
1 stop15h 35m
Multiple Airlines
Deal found 2/4$414
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 3/511:48 am
SWF
-
MSP
1 stop8h 44m
Multiple Airlines
Sun 3/88:04 pm
MSP
-
SWF
1 stop13h 08m
Multiple Airlines
Deal found 2/1$418
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 6/1810:28 am
SWF
-
ORD
1 stop10h 20m
Multiple Airlines
Sun 6/2112:41 pm
ORD
-
SWF
1 stop19h 08m
Multiple Airlines
Deal found 2/3$426
This Kiwi.com deal was found by Cheapflights users on 2/4. 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.
Wed 7/227:46 pm
SWF
-
ORD
1 stop13h 13m
Multiple Airlines
Sat 7/255:32 pm
ORD
-
SWF
1 stop15h 06m
Multiple Airlines
Deal found 2/4$460
This Kiwi.com deal was found by Cheapflights users on 2/2. 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 6/1810:28 am
SWF
-
ORD
1 stop10h 20m
Multiple Airlines
Tue 6/234:10 pm
ORD
-
SWF
2 stops18h 15m
Multiple Airlines
Deal found 2/2$465
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/2610:29 am
SWF
-
ORD
2 stops25h 23m
Multiple Airlines
Mon 3/304:05 pm
ORD
-
SWF
1 stop18h 47m
Multiple Airlines
Deal found 2/3$471
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Wed 2/185:46 pm
SWF
-
MKE
1 stop14h 54m
Multiple Airlines
Fri 2/206:20 pm
MKE
-
SWF
2 stops17h 19m
Multiple Airlines
Deal found 2/3$471
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 8/712:15 pm
SWF
-
MSN
2 stops32h 00m
Breeze Airways
Sat 8/157:55 pm
MSN
-
SWF
1 stop12h 03m
Breeze Airways
Deal found 2/1$488
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 3/2610:29 am
SWF
-
ORD
1 stop10h 22m
Multiple Airlines
Sun 3/293:21 pm
ORD
-
SWF
2 stops16h 36m
Multiple Airlines
Deal found 2/3$494

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 February 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$391
(Kiwi.com)

One-way from

$88
(Kiwi.com)

Popular in

December

Cheapest in

April

Average price

$399
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. 8% potential increase in price ($42 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 5, 2026.
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

Mon 2/9

11:09 am-11:22 am

1 stop25h 13m

Chicago O'Hare Intl

Sun 2/15

1:17 pm-11:31 am

2 stops21h 14m

$388

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Wed 2/18

5:46 pm-10:46 am

1 stop18h 00m

Chicago O'Hare Intl

Thu 2/19

3:40 pm-10:14 am

2 stops17h 34m

$391

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Sun 5/17

9:38 am-8:25 am

2 stops23h 47m

Madison Truax Field

Fri 5/22

6:50 pm-11:25 am

1 stop15h 35m

$414

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Thu 3/5

11:48 am-7:32 pm

1 stop8h 44m

Minneapolis St Paul

Sun 3/8

8:04 pm-10:12 am

1 stop13h 08m

$418

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 3/26

10:29 am-10:52 am

2 stops25h 23m

Chicago O'Hare Intl

Mon 3/30

4:05 pm-11:52 am

1 stop18h 47m

$471

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Wed 2/18

5:46 pm-7:40 am

1 stop14h 54m

Milwaukee-Mitchell

Fri 2/20

6:20 pm-12:39 pm

2 stops17h 19m

$471

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Thu 3/26

10:29 am-7:51 pm

1 stop10h 22m

Chicago O'Hare Intl

Sun 3/29

3:21 pm-8:57 am

2 stops16h 36m

$494

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Fri 3/20

9:42 am-8:06 pm

1 stop11h 24m

Milwaukee-Mitchell

Sun 3/22

9:01 pm-8:57 am

1 stop10h 56m

$513

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Thu 6/18

10:28 am-8:51 am

1 stop23h 23m

Appleton Intl

Sun 6/21

4:49 pm-6:38 pm

1 stop24h 49m

$521

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 3/19

11:48 am-8:06 pm

1 stop9h 18m

Milwaukee-Mitchell

Sun 3/22

9:01 pm-8:57 am

1 stop10h 56m

$552

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 56 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 23h 23m. 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 - Chicago O'Hare Intl or New Windsor Stewart - Milwaukee-Mitchell, New Windsor Stewart - Minneapolis St Paul 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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