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$91+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MKE
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
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 July 25, 2025.

Round-trip from

$194
(Mytrip)

One-way from

$91
(Mytrip)

Popular in

December

Cheapest in

September

Average price

$399
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. 6% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 25, 2025.

This Mytrip deal was found by Cheapflights users on 7/24. 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 8/225:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Sun 8/245:16 pmORD - SWF
1 stop15h 56mMultiple Airlines
Deal found 7/24$206
This Mytrip deal was found by Cheapflights users on 7/23. 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 8/87:56 pmSWF - MSP
2 stops26h 53mMultiple Airlines
Sun 8/105:47 pmMSP - SWF
2 stops24h 19mMultiple Airlines
Deal found 7/23$300
This Mytrip deal was found by Cheapflights users on 7/24. 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 8/17:56 pmSWF - MKE
2 stops20h 46mMultiple Airlines
Sun 8/32:51 pmMKE - SWF
2 stops27h 15mMultiple Airlines
Deal found 7/24$473
This Gotogate deal was found by Cheapflights users on 7/22. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/512:36 pmSWF - MSN
1 stop22h 03mBreeze Airways
Sat 8/910:19 amMSN - SWF
1 stop7h 30mBreeze Airways
Deal found 7/22$605

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 July 25, 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 8/22

5:36 pm-10:31 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

$206

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Fri 8/8

7:56 pm-9:49 pm

2 stops26h 53m

Minneapolis St Paul

Sun 8/10

5:47 pm-7:06 pm

2 stops24h 19m

$300

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Thu 8/7

6:42 pm-3:42 pm

2 stops22h 00m

Milwaukee-Mitchell

Sun 8/10

2:51 pm-7:06 pm

2 stops27h 15m

$480

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 8/5

12:36 pm-9:39 am

1 stop22h 03m

Madison Truax Field

Sat 8/9

10:19 am-6:49 pm

1 stop7h 30m

$605

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$91

New WindsorMinneapolis

SWF - MSP

SWFMSP

New Windsor Stewart

Mon 8/11

7:56 pm-4:52 pm

2 stops21h 56m

$129

New WindsorMilwaukee

SWF - MKE

SWFMKE

New Windsor Stewart

Mon 8/4

7:56 pm-3:42 pm

2 stops20h 46m

$156

New WindsorAppleton

SWF - ATW

SWFATW

New Windsor Stewart

Thu 9/4

2:04 pm-12:16 pm

3 stops23h 12m

$209

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 8/29

1:55 pm-9:39 am

2 stops20h 44m

$232

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 9/2

12:36 pm-5:28 pm

1 stop29h 52m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

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.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated July 25, 2025.
Get a feel of what it's like to fly with Breeze Airways from New Windsor to Wisconsin by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
189 reviews

Boarding

8.3

Overall

8.0

Food

6.7

Entertainment

6.6

Comfort

8.1

Crew

8.7

Reviews

1 / 12
2.0
Mediocre

Andrew,Jul 2025

CHS - PWM

One word-AWFUL! If you can, avoid this airline like the plague! Rude gate supervisor-rude flight attendant AFTER they delayed the plane for 4 hours! Zero Fs given by them-only got real answers and genuine apologies from the pilots themselves. Febreeze, as I’m calling them, stinks!
Breeze Airways
8.0
Very good
189 reviews
Breeze Airways
8.0
Very good
189 reviews

Boarding

8.3

Overall

8.0

Food

6.7

Entertainment

6.6

Comfort

8.1

Crew

8.7

Reviews

1 / 12
2.0
Mediocre

Andrew,Jul 2025

CHS - PWM

One word-AWFUL! If you can, avoid this airline like the plague! Rude gate supervisor-rude flight attendant AFTER they delayed the plane for 4 hours! Zero Fs given by them-only got real answers and genuine apologies from the pilots themselves. Febreeze, as I’m calling them, stinks!

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.

  • 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 - Milwaukee-Mitchell, 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.

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