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Stewart

$127+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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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 August 2, 2025.

Round-trip from

$212
(Mytrip)

One-way from

$127
(Mytrip)

Popular in

March

Cheapest in

October

Average price

$279
From Wisconsin to New Windsor Stewart
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One-way flight from Wisconsin to New Windsor Stewart
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Highest demand for flights based on searches. 6% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 2, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Mon 10/611:01 amSWF - ORD
1 stop12h 47mMultiple Airlines
Deal found 7/31$230
This Mytrip deal was found by Cheapflights users on 8/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/75:47 pmMSP - SWF
2 stops24h 19mMultiple Airlines
Mon 8/117:56 pmSWF - MSP
2 stops21h 56mMultiple Airlines
Deal found 8/1$290
This Mytrip deal was found by Cheapflights users on 7/31. 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 8/74:37 pmMKE - SWF
2 stops25h 29mMultiple Airlines
Sun 8/106:42 pmSWF - MKE
2 stops22h 00mMultiple Airlines
Deal found 7/31$526
This Booking.com deal was found by Cheapflights users on 7/31. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/246:08 pmMSN - SWF
1 stop15h 45mBreeze Airways
Fri 9/2612:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Deal found 7/31$586

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 August 2, 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 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-10:48 pm

1 stop12h 47m

$230

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Thu 8/28

9:22 am-1:05 pm

2 stops26h 43m

New Windsor Stewart

Mon 9/1

1:55 pm-8:17 am

2 stops19h 22m

$346

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 8/7

4:37 pm-7:06 pm

2 stops25h 29m

New Windsor Stewart

Sun 8/10

6:42 pm-3:42 pm

2 stops22h 00m

$526

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 9/24

6:08 pm-10:53 am

1 stop15h 45m

New Windsor Stewart

Fri 9/26

12:24 pm-5:28 pm

2 stops30h 04m

$586

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 8/30

5:21 pm-11:23 am

1 stop17h 02m

$127

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Thu 8/7

5:47 pm-7:06 pm

2 stops24h 19m

$142

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Fri 8/8

1:09 pm-10:13 am

2 stops20h 04m

$199

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Fri 8/8

4:37 pm-10:13 am

1 stop16h 36m

$225

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 9/10

6:08 pm-10:53 am

1 stop15h 45m

$307

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 8/23

6:25 pm-11:23 am

1 stop15h 58m

$366

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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, October is the cheapest month in which you can book a flight from Wisconsin to New Windsor (average of $109). Flying from Wisconsin to New Windsor in August is currently the most expensive (average of $206). 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 Stewart

Get insights into the airlines that provide service to Stewart. 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 Stewart. Reviews last updated August 2, 2025.
Read reviews from past customers who have flown Breeze Airways and Allegiant Air from Wisconsin to New Windsor. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.5

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Breeze Airways
8.0
Very good
191 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.5

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!
Allegiant Air
7.2
Good
702 reviews
Breeze Airways
8.0
Very good
191 reviews

Comfort

8.1

Overall

8.0

Boarding

8.2

Crew

8.7

Entertainment

6.5

Food

6.7

Reviews

1 / 13
8.0
Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

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 Minneapolis St Paul - 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, October is the cheapest month in which you can book a flight from Wisconsin to New Windsor (average of $109). Flying from Wisconsin to New Windsor in August is currently the most expensive (average of $206). 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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