$261+ Cheap flights from Milwaukee (MKE) to Westchester County
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — HPN
Jul 29 — Aug 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Milwaukee to Westchester County with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Milwaukee to Westchester County
Cheapest
Best
Last-minute
One-way
Cheapest flights from Milwaukee to Westchester CountyExplore the most affordable flight options available from Milwaukee to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 29, 2026.
Explore the most affordable flight options available from Milwaukee to Westchester County. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 29, 2026.
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- HPN
1 stop7h 32m
American Airlines
Tue 8/114:30 pm
HPN
- MKE
1 stop4h 29m
American Airlines
Deal found 6/29![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 8/65:34 am
MKE
- HPN
1 stop5h 29m
Delta
Sat 8/86:49 pm
HPN
- MKE
1 stop6h 04m
Delta
Deal found 6/25![Delta logo]()
$289
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/711:32 am
MKE
- HPN
1 stop4h 43m
American Airlines
Sun 8/95:24 pm
HPN
- MKE
1 stop7h 35m
American Airlines
Deal found 6/28![American Airlines logo]()
$317
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 7/169:39 am
MKE
- HPN
1 stop5h 08m
Delta
Sat 7/186:49 pm
HPN
- MKE
1 stop5h 54m
Delta
Deal found 6/25![Delta logo]()
$348
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:59 pm
MKE
- HPN
1 stop6h 26m
Delta
Fri 7/2412:54 pm
HPN
- MKE
1 stop5h 46m
Delta
Deal found 6/26![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/178:43 am
MKE
- HPN
1 stop6h 16m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/24![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Thu 7/168:43 am
MKE
- HPN
1 stop7h 32m
American Airlines
Sun 7/195:34 pm
HPN
- MKE
1 stop4h 27m
American Airlines
Deal found 6/26![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 12/236:05 am
MKE
- HPN
1 stop7h 25m
American Airlines
Wed 12/305:16 pm
HPN
- MKE
1 stop5h 15m
American Airlines
Deal found 6/27![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/273:01 pm
MKE
- HPN
1 stop6h 24m
Delta
Sun 6/286:29 am
HPN
- MKE
1 stop6h 22m
Delta
Deal found 6/26![Delta logo]()
$383
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:04 pm
MKE
- HPN
1 stop4h 24m
American Airlines
Sun 7/124:39 pm
HPN
- MKE
1 stop5h 22m
American Airlines
Deal found 6/28![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 7/151:15 pm
MKE
- HPN
1 stop7h 43m
American Airlines
Mon 7/205:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$428
Best flights from Milwaukee to Westchester CountyDiscover carefully curated flight deals from Milwaukee to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 29, 2026.
Discover carefully curated flight deals from Milwaukee to Westchester County that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 29, 2026.
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:43 am
MKE
- HPN
1 stop7h 32m
American Airlines
Tue 8/114:30 pm
HPN
- MKE
1 stop4h 29m
American Airlines
Deal found 6/29![American Airlines logo]()
$261
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 8/65:34 am
MKE
- HPN
1 stop5h 29m
Delta
Sat 8/86:49 pm
HPN
- MKE
1 stop6h 04m
Delta
Deal found 6/25![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 7/169:39 am
MKE
- HPN
1 stop5h 08m
Delta
Sat 7/186:49 pm
HPN
- MKE
1 stop5h 54m
Delta
Deal found 6/25![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/178:43 am
MKE
- HPN
1 stop6h 16m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/24![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:59 pm
MKE
- HPN
1 stop6h 26m
Delta
Fri 7/2412:54 pm
HPN
- MKE
1 stop5h 46m
Delta
Deal found 6/26![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Thu 7/166:00 am
MKE
- HPN
1 stop7h 30m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$384
This KAYAK deal was found by Cheapflights users on 6/25. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:01 am
MKE
- HPN
1 stop4h 28m
American Airlines
Thu 8/64:30 pm
HPN
- MKE
1 stop5h 30m
American Airlines
Deal found 6/25![American Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 6/27. 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 12/47:00 am
MKE
- HPN
1 stop3h 45m
Delta
Sun 12/66:00 am
HPN
- MKE
1 stop6h 15m
Delta
Deal found 6/27![Delta logo]()
$474
This American Airlines deal was found by Cheapflights users on 6/27. 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.
Wed 12/2311:42 am
MKE
- HPN
2 stops7h 45m
American Airlines
Wed 12/305:16 pm
HPN
- MKE
1 stop5h 15m
American Airlines
Deal found 6/27![American Airlines logo]()
$791
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Thu 7/166:01 am
MKE
- HPN
1 stop4h 28m
American Airlines
Fri 7/2411:00 am
HPN
- MKE
2 stops7h 17m
American Airlines
Deal found 6/26![American Airlines logo]()
$881
Last-minute flights from Milwaukee to Westchester CountyDiscover last-minute flight deals from Milwaukee to Westchester County. Data last updated June 29, 2026 and is based on user searches.
Discover last-minute flight deals from Milwaukee to Westchester County. Data last updated June 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:04 pm
MKE
- HPN
1 stop4h 24m
American Airlines
Sun 7/124:39 pm
HPN
- MKE
1 stop5h 22m
American Airlines
Deal found 6/28![American Airlines logo]()
$404
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 7/151:15 pm
MKE
- HPN
1 stop7h 43m
American Airlines
Mon 7/205:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 7/156:01 am
MKE
- HPN
1 stop4h 28m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$463
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 7/169:39 am
MKE
- HPN
1 stop5h 08m
Delta
Sat 7/186:49 pm
HPN
- MKE
1 stop5h 54m
Delta
Deal found 6/25![Delta logo]()
$348
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Thu 7/168:43 am
MKE
- HPN
1 stop6h 16m
American Airlines
Fri 7/244:39 pm
HPN
- MKE
1 stop6h 42m
American Airlines
Deal found 6/26![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Thu 7/166:00 am
MKE
- HPN
1 stop7h 30m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Thu 7/166:00 am
MKE
- HPN
1 stop7h 30m
American Airlines
Mon 7/205:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 6/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/172:59 pm
MKE
- HPN
1 stop6h 26m
Delta
Fri 7/2412:54 pm
HPN
- MKE
1 stop5h 46m
Delta
Deal found 6/26![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 6/24. 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.
Fri 7/178:43 am
MKE
- HPN
1 stop6h 16m
American Airlines
Sun 7/195:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/24![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Fri 7/176:00 am
MKE
- HPN
1 stop7h 30m
American Airlines
Mon 7/205:26 pm
HPN
- MKE
1 stop6h 43m
American Airlines
Deal found 6/25![American Airlines logo]()
$464
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Wed 7/297:25 am
MKE
- HPN
1 stop7h 34m
American Airlines
Fri 7/311:43 pm
HPN
- MKE
1 stop4h 54m
American Airlines
Deal found 6/25![American Airlines logo]()
$577
One-way flights from Milwaukee to Westchester CountySearch for one-way flight options from Milwaukee to Westchester County. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
Search for one-way flight options from Milwaukee to Westchester County. Find affordable one-way fares based on user searches. Data last updated June 29, 2026.
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/83:59 pm
MKE
- HPN
1 stop5h 22m
Delta
Deal found 6/29![Delta logo]()
$289
This Delta deal was found by Cheapflights users on 6/25. 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.
Thu 7/169:39 am
MKE
- HPN
1 stop5h 08m
Delta
Deal found 6/25![Delta logo]()
$294
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/77:09 am
MKE
- HPN
1 stop3h 47m
Delta
Deal found 6/29![Delta logo]()
$320
This Delta deal was found by Cheapflights users on 6/25. 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 7/159:39 am
MKE
- HPN
1 stop5h 08m
Delta
Deal found 6/25![Delta logo]()
$370
This Delta deal was found by Cheapflights users on 6/25. 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.
Mon 7/65:40 am
MKE
- HPN
1 stop5h 34m
Delta
Deal found 6/25![Delta logo]()
$395
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/87:00 am
MKE
- HPN
2 stops14h 50m
American Airlines
Deal found 6/29![American Airlines logo]()
$423
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
MKE
- HPN
2 stops15h 29m
American Airlines
Deal found 6/29![American Airlines logo]()
$514
This Delta deal was found by Cheapflights users on 6/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/96:48 pm
MKE
- HPN
2 stops16h 15m
Delta
Deal found 6/29![Delta logo]()
$523
This American Airlines deal was found by Cheapflights users on 6/26. 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.
Fri 7/176:40 pm
MKE
- HPN
2 stops17h 33m
American Airlines
Deal found 6/26![American Airlines logo]()
$546
This American Airlines deal was found by Cheapflights users on 6/27. 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 8/215:00 am
MKE
- HPN
2 stops8h 51m
American Airlines
Deal found 6/27![American Airlines logo]()
$627
Find flight deals from Milwaukee to Westchester County
Keep the following information in mind while searching for Milwaukee to Westchester County flight deals. Data was last updated June 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $261 (American Airlines) |
Popular in | November |
Cheapest in | January |
Average price | $418 |
Cheapflights Fare Finder
Customize your flight search to find flights from Milwaukee 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 June 29, 2026.
Use the filters below to find and compare flights from Milwaukee to Westchester County that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Tue 8/4
8:43 am-5:15 pm
1 stop7h 32m
White Plains Westchester County
Tue 8/11
4:30 pm-7:59 pm
1 stop4h 29m
$261
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Thu 8/6
5:34 am-12:03 pm
1 stop5h 29m
White Plains Westchester County
Sat 8/8
6:49 pm-11:53 pm
1 stop6h 04m
$289
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Thu 7/16
9:39 am-3:47 pm
1 stop5h 08m
White Plains Westchester County
Sat 7/18
6:49 pm-11:43 pm
1 stop5h 54m
$348
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Fri 7/17
2:59 pm-10:25 pm
1 stop6h 26m
White Plains Westchester County
Fri 7/24
12:54 pm-5:40 pm
1 stop5h 46m
$349
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Fri 7/17
8:43 am-3:59 pm
1 stop6h 16m
White Plains Westchester County
Sun 7/19
5:26 pm-11:09 pm
1 stop6h 43m
$351
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Thu 7/16
6:00 am-2:30 pm
1 stop7h 30m
White Plains Westchester County
Sun 7/19
5:26 pm-11:09 pm
1 stop6h 43m
$384
Quickest round-trip
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Mon 8/3
6:01 am-11:29 am
1 stop4h 28m
White Plains Westchester County
Thu 8/6
4:30 pm-9:00 pm
1 stop5h 30m
$456
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Fri 12/4
7:00 am-11:45 am
1 stop3h 45m
White Plains Westchester County
Sun 12/6
6:00 am-11:15 am
1 stop6h 15m
$474
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Wed 12/23
11:42 am-8:27 pm
2 stops7h 45m
White Plains Westchester County
Wed 12/30
5:16 pm-9:31 pm
1 stop5h 15m
$791
MilwaukeeWhite Plains
MKE - HPN
MKEHPN
Milwaukee-Mitchell
Thu 7/16
6:01 am-11:29 am
1 stop4h 28m
White Plains Westchester County
Fri 7/24
11:00 am-5:17 pm
2 stops7h 17m
$881
Showing 1-10 of 19 resultsSorted by cheapest first
Best time to book a flight from Milwaukee to Westchester County
Have a flexible travel schedule? Discover the best time to fly to Westchester County from Milwaukee with our price prediction graph.
MKE-HPN
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 Milwaukee to Westchester County
MKE-zzREU
MKE-HPN
What is the cheapest month to book a flight from Milwaukee to Westchester County?
Currently, February is the cheapest month in which you can book a flight from Milwaukee to Westchester County (average of $206). Flying from Milwaukee to Westchester County in November is currently the most expensive (average of $375). 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
Get insights into the airlines that provide service to Westchester County. 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 Westchester County. Reviews last updated June 29, 2026.
Get a feel of what it's like to fly with Delta and American Airlines from Milwaukee to Westchester County by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.8
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentLucy,Nov 2023
ATL - JFK
Overall
7.8
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentLucy,Nov 2023
ATL - JFK
Overall
7.8
Boarding
8.1
Entertainment
7.8
Comfort
7.8
Food
7.2
Crew
8.5
Reviews
1 / 20
10.0
ExcellentLucy,Nov 2023
ATL - JFK
Related info for your journey
Find useful and relevant information for your journey from Milwaukee to Westchester County. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
Alternative routes for Milwaukee to Westchester County
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Westchester County by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Milwaukee to Westchester County by cabin class
Find flights from Milwaukee to Westchester County, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Milwaukee and Westchester County flights
Browse other Milwaukee and Westchester County flight options. Last updated on June 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Milwaukee to Westchester County flights
Consider these flights traveling from Milwaukee to Westchester County.
Top 2 airlines flying from Milwaukee to Westchester County
Discover the top 2 airlines that operate flights from Milwaukee 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 June 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$206 | Average$302 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$366 | FlexibilityNo cancel fee | On-time71% |