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Stewart

$122+ 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 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — SWF
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$254
(Mytrip)

One-way from

$122
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$339
Provider with most accurate pricing for Milwaukee-Mitchell-New York (NYC) flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-New York (NYC) flights.
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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. 13% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 30, 2025.

This Mytrip deal was found by Cheapflights users on 4/29. 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 5/229:55 amORD - SWF
1 stop24h 10mMultiple Airlines
Mon 5/2611:55 amSWF - ORD
1 stop21h 55mMultiple Airlines
Deal found 4/29$254
This Mytrip deal was found by Cheapflights users on 4/28. 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 7/102:22 pmMSP - SWF
2 stops27h 44mMultiple Airlines
Mon 7/147:56 pmSWF - MSP
2 stops18h 21mMultiple Airlines
Deal found 4/28$285
This Mytrip deal was found by Cheapflights users on 4/29. 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 5/45:00 pmMKE - SWF
1 stop17h 00mMultiple Airlines
Sun 5/115:53 pmSWF - MKE
2 stops18h 34mMultiple Airlines
Deal found 4/29$515
This FlightHub deal was found by Cheapflights users on 4/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/315:05 pmMSN - SWF
1 stop17h 21mBreeze Airways
Fri 6/61:28 pmSWF - MSN
2 stops21h 11mBreeze Airways
Deal found 4/29$617

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 April 30, 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 5/22

9:55 am-11:05 am

1 stop24h 10m

New Windsor Stewart

Mon 5/26

11:55 am-8:50 am

1 stop21h 55m

$254

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Thu 7/10

2:22 pm-7:06 pm

2 stops27h 44m

New Windsor Stewart

Mon 7/14

7:56 pm-1:17 pm

2 stops18h 21m

$285

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Sun 5/4

5:00 pm-11:00 am

1 stop17h 00m

New Windsor Stewart

Sun 5/11

5:53 pm-11:27 am

2 stops18h 34m

$515

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 5/31

5:05 pm-11:26 am

1 stop17h 21m

New Windsor Stewart

Fri 6/6

1:28 pm-9:39 am

2 stops21h 11m

$617

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 5/29

9:55 am-11:05 am

1 stop24h 10m

$122

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Sun 6/22

7:25 pm-7:11 pm

2 stops22h 46m

$154

MinneapolisNew Windsor

MSP - SWF

MSPSWF

Minneapolis St Paul

Thu 6/12

8:02 am-5:06 pm

2 stops32h 04m

$174

MilwaukeeNew Windsor

MKE - SWF

MKESWF

Milwaukee-Mitchell

Thu 5/22

12:22 pm-11:05 am

2 stops21h 43m

$266

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 5/21

6:25 pm-10:33 am

1 stop15h 08m

$267

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 5/21

5:05 pm-11:26 am

1 stop17h 21m

$281

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/29

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 $223). 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 April 30, 2025.
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Boarding

8.3

Overall

8.1

Crew

8.8

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
160 reviews
Breeze Airways
8.1
Very good
160 reviews

Entertainment

6.6

Boarding

8.3

Overall

8.1

Crew

8.8

Food

6.7

Comfort

8.2

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 $223). 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 Wisconsin?

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Kingston

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