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Westchester County

$78+ 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 12/7. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HPN
Nov 20 — Nov 271
Thu 11/20
Thu 11/27
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 October 21, 2025.

This Delta deal was found by Cheapflights users on 10/21. 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.
Thu 12/45:45 amMKE - HPN
1 stop5h 15mDelta
Mon 12/84:29 pmHPN - MKE
1 stop8h 25mDelta
Deal found 10/21$207
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 11/131:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Mon 11/171:20 pmHPN - ORD
2 stops27h 55mMultiple Airlines
Deal found 10/20$217
This American Airlines deal was found by Cheapflights users on 10/19. 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.
Fri 11/76:00 amMKE - HPN
1 stop3h 57mAmerican Airlines
Mon 11/104:30 pmHPN - MKE
1 stop7h 35mAmerican Airlines
Deal found 10/19$236
This Delta deal was found by Cheapflights users on 10/20. 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.
Tue 11/49:39 amMKE - HPN
1 stop5h 10mDelta
Sat 11/85:20 pmHPN - MKE
1 stop7h 35mDelta
Deal found 10/20$265
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/264:58 pmORD - HPN
2 stops17h 31mMultiple Airlines
Wed 12/31:14 pmHPN - ORD
1 stop24h 54mMultiple Airlines
Deal found 10/21$268
This Delta deal was found by Cheapflights users on 10/21. 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 10/295:47 amMKE - HPN
1 stop5h 13mDelta
Wed 11/56:50 pmHPN - MKE
1 stop6h 05mDelta
Deal found 10/21$284
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Thu 11/131:50 pmORD - HPN
1 stop20h 38mMultiple Airlines
Sun 11/161:19 pmHPN - ORD
2 stops26h 12mMultiple Airlines
Deal found 10/20$291
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 11/264:58 pmORD - HPN
2 stops17h 31mMultiple Airlines
Fri 12/512:10 pmHPN - ORD
1 stop9h 32mMultiple Airlines
Deal found 10/21$307
This Delta deal was found by Cheapflights users on 10/19. 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.
Sat 12/135:38 amMSN - HPN
1 stop5h 22mDelta
Wed 12/176:10 amHPN - MSN
1 stop5h 49mDelta
Deal found 10/19$307
This Delta deal was found by Cheapflights users on 10/19. 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.
Sun 12/145:31 amATW - HPN
1 stop5h 29mDelta
Tue 12/1612:55 pmHPN - ATW
1 stop5h 19mDelta
Deal found 10/19$313
This Kiwi.com deal was found by Cheapflights users on 10/19. 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 11/35:15 amORD - HPN
2 stops29h 14mMultiple Airlines
Fri 11/712:10 pmHPN - ORD
1 stop12h 18mMultiple Airlines
Deal found 10/19$319
This Delta deal was found by Cheapflights users on 10/19. 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 12/512:50 pmMSP - HPN
Nonstop2h 47mDelta
Mon 12/83:08 pmHPN - MSP
Nonstop3h 11mDelta
Deal found 10/19$319

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 October 21, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Delta)

One-way from

$78
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$359
Provider with most accurate pricing for Milwaukee-Mitchell-New York (NYC) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-New York (NYC) flights.
Search Deals
From Wisconsin to Westchester County
Search Deals
One-way flight from Wisconsin to Westchester County
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 21, 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

Mon 12/8

5:45 am-12:00 pm

1 stop5h 15m

White Plains Westchester County

Sat 12/13

12:45 pm-7:10 pm

1 stop7h 25m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Thu 12/4

11:16 am-5:29 pm

1 stop5h 13m

White Plains Westchester County

Mon 12/8

6:43 pm-11:01 pm

1 stop5h 18m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Sat 12/6

3:17 pm-10:09 pm

1 stop5h 52m

White Plains Westchester County

Sat 12/13

5:20 pm-11:40 pm

1 stop7h 20m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Thu 12/4

5:45 am-12:00 pm

1 stop5h 15m

White Plains Westchester County

Mon 12/8

4:29 pm-11:54 pm

1 stop8h 25m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 12/5

3:17 pm-10:09 pm

1 stop5h 52m

White Plains Westchester County

Mon 12/8

6:50 pm-11:54 pm

1 stop6h 04m

$207

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Wed 12/3

5:45 am-12:00 pm

1 stop5h 15m

White Plains Westchester County

Sun 12/7

6:10 am-10:46 am

1 stop5h 36m

$207

ChicagoWhite Plains

ORD - HPN

ORDHPN

Chicago O'Hare Intl

Thu 11/13

1:50 pm-11:28 am

1 stop20h 38m

White Plains Westchester County

Mon 11/17

1:20 pm-4:15 pm

2 stops27h 55m

$217

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 11/7

6:00 am-10:57 am

1 stop3h 57m

White Plains Westchester County

Mon 11/10

4:30 pm-11:05 pm

1 stop7h 35m

$236

MilwaukeeWhite Plains

MKE - HPN

MKEHPN

Milwaukee-Mitchell

Fri 10/31

2:04 pm-10:09 pm

1 stop7h 05m

White Plains Westchester County

Tue 11/4

6:50 pm-11:55 pm

1 stop6h 05m

$236

AppletonWhite Plains

ATW - HPN

ATWHPN

Appleton Intl

Wed 2/25

7:00 am-11:50 am

1 stop3h 50m

White Plains Westchester County

Sat 2/28

12:45 pm-4:42 pm

1 stop4h 57m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/21

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 5h 13m. Your travel time can differ by up to 02m. 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 October 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$445FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$213Average$405FlexibilityNo cancel feeOn-time71%

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