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Westchester County

$76+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HPN
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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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 November 26, 2025.

This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/103:17 pmMKE - HPN
1 stop5h 52mDelta
Fri 12/123:08 pmHPN - MKE
1 stop7h 13mDelta
Deal found 11/24$257
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/812:09 pmORD - HPN
2 stops22h 20mMultiple Airlines
Wed 12/101:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 11/24$294
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/511:41 amMKE - HPN
1 stop5h 19mDelta
Sun 12/76:10 amHPN - MKE
1 stop5h 36mDelta
Deal found 11/25$313
This Kiwi.com deal was found by Cheapflights users on 11/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/146:00 amORD - HPN
1 stop28h 28mMultiple Airlines
Tue 12/1612:09 pmHPN - ORD
2 stops10h 39mMultiple Airlines
Deal found 11/24$320
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/164:30 pmMKE - HPN
1 stop5h 59mAmerican Airlines
Mon 12/226:56 pmHPN - MKE
1 stop6h 02mAmerican Airlines
Deal found 11/25$333
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/308:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Sat 1/36:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 11/25$349
This Delta deal was found by Cheapflights users on 11/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:00 amGRB - HPN
1 stop3h 59mDelta
Wed 12/312:55 pmHPN - GRB
1 stop4h 12mDelta
Deal found 11/25$354
This American Airlines deal was found by Cheapflights users on 11/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2011:19 amMKE - HPN
1 stop5h 07mAmerican Airlines
Sat 12/275:16 pmHPN - MKE
1 stop5h 00mAmerican Airlines
Deal found 11/24$378
This American Airlines deal was found by Cheapflights users on 11/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/3012:50 pmORD - HPN
Nonstop2h 09mAmerican Airlines
Sun 1/46:27 amHPN - ORD
Nonstop2h 48mAmerican Airlines
Deal found 11/25$380
This Kiwi.com deal was found by Cheapflights users on 11/25. 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 12/32:01 pmORD - HPN
2 stops21h 38mMultiple Airlines
Fri 12/512:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 11/25$386
This American Airlines deal was found by Cheapflights users on 11/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Sat 1/176:00 amHPN - ORD
Nonstop2h 52mAmerican Airlines
Deal found 11/26$399
This Delta deal was found by Cheapflights users on 11/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1212:50 pmMSP - HPN
Nonstop2h 47mDelta
Mon 12/153:08 pmHPN - MSP
Nonstop3h 11mDelta
Deal found 11/24$399

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 November 26, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$180
(Kiwi.com)

One-way from

$76
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$419
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
Search Deals
One-way flight from Wisconsin to Westchester County
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Wisconsin to Westchester County 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 November 26, 2025.
Use the filters below to find and compare flights from Wisconsin to Westchester County that are best for you.

Fly from

Wisconsin

Fly to

Westchester County

Route

Depart

Return

Price

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 2/6

3:42 pm-10:00 pm

1 stop5h 18m

White Plains Westchester County

Mon 2/9

3:10 pm-9:30 pm

1 stop7h 20m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 2/6

4:05 pm-9:55 pm

1 stop4h 50m

White Plains Westchester County

Mon 2/9

12:00 pm-3:57 pm

1 stop4h 57m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Sat 1/31

2:45 pm-10:00 pm

1 stop6h 15m

White Plains Westchester County

Tue 2/3

12:59 pm-5:34 pm

1 stop5h 35m

$207

Green BayWhite Plains

GRB - HPN

GRBHPN

Green Bay Austin-Straubel

Tue 1/27

7:00 am-11:56 am

1 stop3h 56m

White Plains Westchester County

Sat 1/31

3:10 pm-9:35 pm

1 stop7h 25m

$249

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Wed 12/10

3:17 pm-10:09 pm

1 stop5h 52m

White Plains Westchester County

Fri 12/12

3:08 pm-9:21 pm

1 stop7h 13m

$257

AppletonWhite Plains

ATW - HPN

ATWHPN

Appleton Intl

Wed 1/7

5:20 am-12:06 pm

1 stop5h 46m

White Plains Westchester County

Sat 1/10

3:10 pm-9:29 pm

1 stop7h 19m

$272

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Thu 1/1

6:00 am-11:29 am

1 stop4h 29m

White Plains Westchester County

Wed 1/7

10:00 am-3:27 pm

1 stop6h 27m

$307

MadisonWhite Plains

MSN - HPN

MSNHPN

Madison Truax Field

Sat 1/10

11:00 am-4:35 pm

1 stop4h 35m

White Plains Westchester County

Wed 1/14

10:29 am-4:17 pm

1 stop6h 48m

$307

MinneapolisWhite Plains

MSP - HPN

MSPHPN

Minneapolis St Paul

Fri 1/9

12:45 pm-4:32 pm

Nonstop2h 47m

White Plains Westchester County

Sun 1/11

3:10 pm-5:25 pm

Nonstop3h 15m

$319

MinneapolisWhite Plains

MSP - HPN

MSPHPN

Minneapolis St Paul

Fri 1/16

12:45 pm-4:32 pm

Nonstop2h 47m

White Plains Westchester County

Sun 1/18

3:10 pm-5:25 pm

Nonstop3h 15m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 60 results
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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, April is the cheapest month in which you can book a flight from Wisconsin to Westchester County (average of $148). Flying from Wisconsin to Westchester County in February is currently the most expensive (average of $378). 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 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.

  • How long is the flight from Wisconsin to Westchester County?

    Delta and American Airlines can get you from Wisconsin to Westchester County in just under 4h 50m. Your travel time can differ by up to 28m. Airlines will cover a distance of 739 mi. This flight may include one or multiple stops.

  • 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, April is the cheapest month in which you can book a flight from Wisconsin to Westchester County (average of $148). Flying from Wisconsin to Westchester County in February is currently the most expensive (average of $378). 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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Alternative routes for Wisconsin to Westchester County

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Wisconsin to Westchester County

Discover the top 2 airlines that operate flights from Wisconsin to Westchester County. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$434FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$213Average$405FlexibilityNo cancel feeOn-time71%

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