How far in advance should I book a flight from Wisconsin to Westchester County?

Find a great deal and save up to 48% by booking at least 61 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Wisconsin to Westchester County within the next two weeks, with the cheapest ticket starting at $217.

What is the cheapest month to fly from Wisconsin to Westchester County?

September is one of the best times of the year to fly to Westchester County from Wisconsin. Prices for September average $299 per person but you can even find prices for as low as $115. The most expensive prices can be found in the month of March. Opting for a September flight can save you 33% on your journey compared to booking in March

What is the cheapest time of day to fly from WI to REU?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Wisconsin to Westchester County as you normally would.

How can I find direct flights from Wisconsin to Westchester County?

After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Westchester County.

Can I find deals for business class flights from Wisconsin to Westchester County?

Yes. Cheapflights offers flight deals from Wisconsin to Westchester County by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$109+ Flights from Wisconsin to Westchester County

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1. Tell us where you want to go

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Cheap flight deals from Wisconsin to Westchester County

Most accurate provider	CheapOair 3 stars
Most trusted provider	CheapOair 3 stars
Round-trip from	$199 (American Airlines)
One-way from	$109 (Delta)
Popular in	March
Cheapest in	September
Average price	$259

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 Westchester County

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One-way flight from Wisconsin to Westchester County

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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 May 2025

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Find flight deals from Wisconsin to Westchester County

Cheapest flights from Wisconsin to Westchester County
Explore the most affordable flight options available from Wisconsin to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Sat 6/146:21 amMKE - HPN

1 stop4h 07mAmerican Airlines

Sat 6/146:59 pmHPN - MKE

1 stop6h 00mAmerican Airlines

Deal found 4/30

$199

Wed 6/41:51 pmMSP - HPN

1 stop7h 56mAmerican Airlines

Mon 6/96:59 pmHPN - MSP

1 stop6h 00mAmerican Airlines

Deal found 5/1

$249

Tue 8/127:00 amMSN - HPN

1 stop3h 44mDelta

Tue 8/196:00 amHPN - MSN

1 stop5h 12mDelta

Deal found 4/30

$299

Tue 6/246:00 amMSP - HPN

1 stop4h 58mDelta

Sat 6/286:44 pmHPN - MSP

1 stop6h 47mDelta

Deal found 4/30

$314

Tue 7/19:49 amORD - HPN

1 stop11h 36mDelta

Fri 7/412:30 pmHPN - ORD

1 stop9h 54mDelta

Deal found 4/30

$337

Sat 6/148:19 amORD - HPN

Nonstop2h 09mAmerican Airlines

Sat 6/217:26 amHPN - ORD

Nonstop2h 34mAmerican Airlines

Deal found 4/30

$349

Sat 11/13:03 pmMSN - HPN

1 stop5h 53mAmerican Airlines

Sun 11/210:22 amHPN - MSN

1 stop4h 46mAmerican Airlines

Deal found 4/30

$373

Tue 5/65:45 amMKE - HPN

1 stop5h 19mDelta

Wed 5/73:09 pmHPN - MKE

1 stop6h 26mDelta

Deal found 4/30

$431

Mon 5/192:19 pmORD - HPN

1 stop20h 10mMultiple Airlines

Tue 6/312:16 pmHPN - ORD

2 stops21h 34mMultiple Airlines

Deal found 4/29

$447

Fri 5/3012:22 pmMKE - HPN

2 stops23h 08mMultiple Airlines

Sun 6/18:10 amHPN - MKE

2 stops28h 17mMultiple Airlines

Deal found 4/30

$501

Fri 5/168:42 amMSP - HPN

1 stop26h 48mMultiple Airlines

Tue 6/35:20 pmHPN - MSP

2 stops21h 28mMultiple Airlines

Deal found 4/30

$563

Best flights from Wisconsin to Westchester County
Discover carefully curated flight deals from Wisconsin to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 1, 2025.

Sat 6/146:21 amMKE - HPN

1 stop4h 07mAmerican Airlines

Sat 6/146:59 pmHPN - MKE

1 stop6h 00mAmerican Airlines

Deal found 4/30

$199

Tue 6/178:56 amMSP - HPN

1 stop5h 49mDelta

Tue 6/246:00 amHPN - MSP

1 stop8h 48mDelta

Deal found 4/29

$249

Fri 5/3012:22 pmMKE - HPN

2 stops23h 08mMultiple Airlines

Sun 6/18:10 amHPN - MKE

2 stops28h 17mMultiple Airlines

Deal found 4/30

$501

Fri 5/1610:48 amMSP - HPN

1 stop6h 14mAmerican Airlines

Tue 6/36:00 amHPN - MSP

1 stop7h 35mAmerican Airlines

Deal found 4/30

$264

Tue 8/127:00 amMSN - HPN

1 stop3h 44mDelta

Tue 8/196:00 amHPN - MSN

1 stop5h 12mDelta

Deal found 4/30

$299

Tue 7/19:49 amORD - HPN

1 stop11h 36mDelta

Fri 7/412:30 pmHPN - ORD

1 stop9h 54mDelta

Deal found 4/30

$337

Sat 6/148:19 amORD - HPN

Nonstop2h 09mAmerican Airlines

Sat 6/217:26 amHPN - ORD

Nonstop2h 34mAmerican Airlines

Deal found 4/30

$349

Fri 6/135:40 amMSN - HPN

1 stop4h 48mAmerican Airlines

Sat 6/216:30 amHPN - MSN

1 stop7h 28mAmerican Airlines

Deal found 4/29

$408

Sat 6/148:19 amORD - HPN

1 stop27h 11mMultiple Airlines

Sat 6/218:10 amHPN - ORD

3 stops16h 35mMultiple Airlines

Deal found 4/30

$525

Mon 6/167:47 amMSP - HPN

2 stops26h 42mMultiple Airlines

Wed 6/188:10 amHPN - MSP

2 stops38h 55mMultiple Airlines

Deal found 4/28

$529

Fri 6/62:59 pmMKE - HPN

1 stop6h 13mDelta

Mon 6/912:55 pmHPN - MKE

2 stops9h 35mDelta

Deal found 4/30

$677

Last-minute flights from Wisconsin to Westchester County
Discover last-minute flight deals from Wisconsin to Westchester County. Data last updated May 1, 2025 and is based on user searches.

Tue 5/68:22 amORD - HPN

Nonstop2h 07mAmerican Airlines

Tue 5/136:00 amHPN - ORD

Nonstop2h 30mAmerican Airlines

Deal found 4/29

$419

Tue 5/65:45 amMKE - HPN

1 stop5h 19mDelta

Wed 5/73:09 pmHPN - MKE

1 stop6h 26mDelta

Deal found 4/30

$431

Wed 5/75:30 amORD - HPN

1 stop7h 59mDelta

Tue 5/135:15 pmHPN - ORD

1 stop4h 06mDelta

Deal found 4/29

$439

Thu 5/86:00 amMSP - HPN

1 stop4h 58mDelta

Mon 5/126:54 pmHPN - MSP

1 stop6h 45mDelta

Deal found 4/30

$369

Thu 5/84:35 pmORD - HPN

2 stops17h 46mMultiple Airlines

Tue 5/1312:16 pmHPN - ORD

2 stops11h 48mMultiple Airlines

Deal found 4/29

$603

Thu 5/85:28 amMSP - HPN

2 stops8h 05mAmerican Airlines

Mon 5/124:59 pmHPN - MSP

1 stop6h 22mAmerican Airlines

Deal found 4/30

$713

Thu 5/158:31 amMSN - HPN

2 stops7h 06mAmerican Airlines

Mon 5/1911:25 amHPN - MSN

1 stop5h 57mAmerican Airlines

Deal found 4/30

$759

Fri 5/168:42 amMSP - HPN

1 stop26h 48mMultiple Airlines

Tue 6/35:20 pmHPN - MSP

2 stops21h 28mMultiple Airlines

Deal found 4/30

$563

Sat 5/1711:01 amMSN - HPN

1 stop3h 48mDelta

Tue 5/206:00 amHPN - MSN

1 stop5h 19mDelta

Deal found 4/29

$332

Mon 5/192:19 pmORD - HPN

1 stop20h 10mMultiple Airlines

Tue 6/312:16 pmHPN - ORD

2 stops21h 34mMultiple Airlines

Deal found 4/29

$447

Fri 5/235:28 amMSP - HPN

1 stop5h 01mAmerican Airlines

Sun 5/257:15 amHPN - MSP

1 stop5h 42mAmerican Airlines

Deal found 4/30

$249

Fri 5/302:51 pmMKE - HPN

1 stop6h 08mAmerican Airlines

Sun 6/16:30 amHPN - MKE

1 stop5h 45mAmerican Airlines

Deal found 4/30

$224

One-way flights from Wisconsin to Westchester County
Search for one-way flight options from Wisconsin to Westchester County. Find affordable one-way fares based on user searches. Data last updated May 1, 2025.

Sat 6/219:41 amMKE - HPN

1 stop5h 18mDelta

Deal found 4/30

$109

Tue 8/195:29 amATW - HPN

1 stop5h 46mDelta

Deal found 4/30

$159

Tue 8/195:30 amGRB - HPN

1 stop5h 45mDelta

Deal found 4/30

$169

Thu 5/1510:48 amMSP - HPN

1 stop6h 14mAmerican Airlines

Deal found 4/30

$229

Wed 5/75:30 amMSN - HPN

1 stop5h 44mDelta

Deal found 4/30

$232

Tue 6/105:51 amORD - HPN

2 stops29h 39mMultiple Airlines

Deal found 4/30

$237

Thu 5/1512:49 pmORD - HPN

Nonstop2h 10mAmerican Airlines

Deal found 5/1

$240

Thu 5/157:10 amORD - HPN

1 stop3h 48mDelta

Deal found 5/1

$250

Mon 5/269:00 amMSP - HPN

1 stop6h 30mDelta

Deal found 4/30

$260

Wed 5/711:13 amMSN - HPN

2 stops11h 16mAmerican Airlines

Deal found 4/30

$272

Sat 5/105:05 pmMSN - HPN

3 stops26h 54mMultiple Airlines

Deal found 4/30

$564

Sat 6/216:21 amMKE - HPN

2 stops10h 58mAmerican Airlines

Deal found 4/30

$623

Cheapflights Fare Finder

Use the filters below to find and compare flights from Wisconsin to Westchester County that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Sat 6/14

6:21 am-11:28 am

1 stop4h 07m

White Plains Westchester County

Sat 6/14

6:59 pm-11:59 pm

1 stop6h 00m

$199

MinneapolisWhite Plains

MSP - HPN

MSPHPN

Minneapolis St Paul

Wed 6/4

1:51 pm-10:47 pm

1 stop7h 56m

White Plains Westchester County

Mon 6/9

6:59 pm-11:59 pm

1 stop6h 00m

$249

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Tue 8/12

7:00 am-11:44 am

1 stop3h 44m

White Plains Westchester County

Tue 8/19

6:00 am-10:12 am

1 stop5h 12m

$299

MinneapolisWhite Plains

MSP - HPN

MSPHPN

Minneapolis St Paul

Tue 6/24

6:00 am-11:58 am

1 stop4h 58m

White Plains Westchester County

Sat 6/28

6:44 pm-12:31 am

1 stop6h 47m

$314

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Tue 7/1

9:49 am-10:25 pm

1 stop11h 36m

White Plains Westchester County

Fri 7/4

12:30 pm-9:24 pm

1 stop9h 54m

$337

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Sat 6/14

8:19 am-11:28 am

Nonstop2h 09m

White Plains Westchester County

Sat 6/21

7:26 am-9:00 am

Nonstop2h 34m

$349

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Fri 6/13

5:40 am-11:28 am

1 stop4h 48m

White Plains Westchester County

Sat 6/21

6:30 am-12:58 pm

1 stop7h 28m

$408

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Mon 5/19

2:19 pm-11:29 am

1 stop20h 10m

White Plains Westchester County

Tue 6/3

12:16 pm-8:50 am

2 stops21h 34m

$447

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 5/30

12:22 pm-12:30 pm

2 stops23h 08m

White Plains Westchester County

Sun 6/1

8:10 am-11:27 am

2 stops28h 17m

$501

MinneapolisWhite Plains

MSP - HPN

MSPHPN

Minneapolis St Paul

Fri 5/16

8:42 am-12:30 pm

1 stop26h 48m

White Plains Westchester County

Tue 6/3

5:20 pm-1:48 pm

2 stops21h 28m

$563

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Showing 1-10 of 24 results

Best time to book a flight from Wisconsin to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County 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 Westchester County

What is the cheapest month to book a flight from Wisconsin to Westchester County?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Westchester County (average of $276). Flying from Wisconsin to Westchester County in March is currently the most expensive (average of $339). 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 Westchester County

Read through reviews of airlines operating flights from Wisconsin to Westchester County, such as Delta and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

8.0

Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

Delta

8.0

Very good

7,934 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

8.0

Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,934 reviews

Reviews

1 / 20

8.0

Excellent

Rona,Feb 2024

MSP - DEN

It was a good experience other than a short delay.

Related info for your journey

Can I find deals for flights from Wisconsin to Westchester County that include hotel bookings?
Yes. In addition to deals on Wisconsin to Westchester County flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Wisconsin to Westchester County?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Westchester County.
Can I find deals for business class flights from Wisconsin to Westchester County?
Yes. Cheapflights offers flight deals from Wisconsin to Westchester County 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 Westchester County?
Currently, January is the cheapest month in which you can book a flight from Wisconsin to Westchester County (average of $276). Flying from Wisconsin to Westchester County in March is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Top 2 airlines flying from Wisconsin to Westchester County

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$179	Average$431	FlexibilityNo cancel fee	On-timeN/A
American Airlines	Cheapest$198	Average$388	FlexibilityNo cancel fee	On-time71%

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$109+ Cheap flights from Wisconsin to Westchester County

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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Wisconsin to Westchester County with Cheapflights

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3. Compare prices and book

Cheap flight deals from Wisconsin to Westchester County

Keep the following information in mind while searching for Wisconsin to Westchester County flight deals. Data was last updated May 1, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Wisconsin to Westchester County

Cheapest flights from Wisconsin to Westchester CountyExplore the most affordable flight options available from Wisconsin to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Explore the most affordable flight options available from Wisconsin to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Wisconsin to Westchester County that are best for you.

Best time to book a flight from Wisconsin to Westchester County

Have a flexible travel schedule? Discover the best time to fly to Westchester County from Wisconsin with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Wisconsin to Westchester County

What is the cheapest month to book a flight from Wisconsin to Westchester County?

Reviews of airlines servicing Westchester County

Read through reviews of airlines operating flights from Wisconsin to Westchester County, such as Delta and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

Can I find deals for flights from Wisconsin to Westchester County that include hotel bookings?

How can I find direct flights from Wisconsin to Westchester County?

Can I find deals for business class flights from Wisconsin to Westchester County?

What is the cheapest month to book a flight from Wisconsin to Westchester County?

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 Westchester County

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Wisconsin to Westchester County

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Book with Flexibility

Travel Smart

Cheapest flights from Wisconsin to Westchester County
Explore the most affordable flight options available from Wisconsin to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.