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White Plains

$129+ Cheap flights from Midway (MDW) to White Plains (HPN)

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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HPN
Jun 14 — Jun 211
Sun 6/14
Sun 6/21
1 adult, Economy
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Cheap flight deals from Midway to White Plains

Cheapest flights from Midway to White Plains
Explore the most affordable flight options available from Midway to White Plains. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 15, 2026.

This Delta deal was found by Cheapflights users on 5/14. 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 8/186:42 pm
MDW
-
HPN
1 stop16h 14m
Delta
Mon 8/245:17 pm
HPN
-
MDW
1 stop17h 00m
Delta
Deal found 5/14$385
This Delta deal was found by Cheapflights users on 5/11. 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 7/76:58 pm
MDW
-
HPN
1 stop15h 58m
Delta
Tue 8/116:49 pm
HPN
-
MDW
2 stops15h 28m
Delta
Deal found 5/11$390
This Delta deal was found by Cheapflights users on 5/11. 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 7/16:58 pm
MDW
-
HPN
1 stop16h 00m
Delta
Sat 8/154:29 pm
HPN
-
MDW
1 stop7h 07m
Delta
Deal found 5/11$400
This Delta deal was found by Cheapflights users on 5/13. 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 5/2710:59 am
MDW
-
HPN
1 stop6h 01m
Delta
Wed 6/244:29 pm
HPN
-
MDW
1 stop6h 48m
Delta
Deal found 5/13$415
This Delta deal was found by Cheapflights users on 5/14. 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 8/176:42 pm
MDW
-
HPN
1 stop16h 14m
Delta
Mon 8/245:17 pm
HPN
-
MDW
1 stop17h 00m
Delta
Deal found 5/14$422
This Delta deal was found by Cheapflights users on 5/11. 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 7/26:58 pm
MDW
-
HPN
1 stop19h 51m
Delta
Tue 8/115:17 pm
HPN
-
MDW
1 stop17h 00m
Delta
Deal found 5/11$427
This Delta deal was found by Cheapflights users on 5/14. 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 7/206:58 pm
MDW
-
HPN
1 stop15h 58m
Delta
Sat 8/112:36 pm
HPN
-
MDW
1 stop6h 31m
Delta
Deal found 5/14$437
This Delta deal was found by Cheapflights users on 5/11. 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 7/26:58 pm
MDW
-
HPN
1 stop19h 51m
Delta
Wed 8/126:00 am
HPN
-
MDW
1 stop4h 59m
Delta
Deal found 5/11$442
This Delta deal was found by Cheapflights users on 5/11. 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 7/16:58 pm
MDW
-
HPN
1 stop16h 00m
Delta
Sun 8/166:00 am
HPN
-
MDW
1 stop4h 59m
Delta
Deal found 5/11$444
This Delta deal was found by Cheapflights users on 5/13. 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 6/109:17 am
MDW
-
HPN
1 stop5h 32m
Delta
Wed 6/1712:38 pm
HPN
-
MDW
1 stop6h 53m
Delta
Deal found 5/13$445
This Delta deal was found by Cheapflights users on 5/14. 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 7/196:00 am
MDW
-
HPN
1 stop5h 08m
Delta
Sat 8/112:36 pm
HPN
-
MDW
1 stop6h 31m
Delta
Deal found 5/14$459

Find flight deals from Midway to White Plains

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to White Plains (HPN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 15, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$385
(Delta)

One-way from

$129
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$228
Provider with most accurate pricing for Chicago Midway-White Plains Westchester County flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago Midway-White Plains Westchester County flights.
Search Deals
From Chicago Midway to White Plains Westchester County
Search Deals
One-way flight from Chicago Midway to White Plains Westchester County
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to White Plains 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 May 15, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to White Plains that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 8/19

6:05 am-12:03 pm

1 stop4h 58m

White Plains Westchester County

Mon 8/24

5:17 pm-9:17 am

1 stop17h 00m

$400

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 5/27

9:22 am-3:49 pm

1 stop5h 27m

White Plains Westchester County

Wed 6/24

6:29 am-12:05 pm

1 stop6h 36m

$415
Quickest round-trip

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 7/4

9:17 am-3:49 pm

1 stop5h 32m

White Plains Westchester County

Wed 8/12

6:00 am-9:59 am

1 stop4h 59m

$415

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 7/22

11:05 am-6:07 pm

1 stop6h 02m

White Plains Westchester County

Mon 7/27

12:36 pm-6:25 pm

1 stop6h 49m

$459

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 6/24

6:00 am-2:28 pm

1 stop7h 28m

White Plains Westchester County

Mon 6/29

4:29 pm-10:17 pm

1 stop6h 48m

$459

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 7/2

6:58 pm-3:49 pm

1 stop19h 51m

White Plains Westchester County

Sun 8/16

6:00 am-9:59 am

1 stop4h 59m

$486

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 6/17

9:17 am-3:49 pm

1 stop5h 32m

White Plains Westchester County

Tue 6/23

6:29 am-12:05 pm

1 stop6h 36m

$487

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Mon 6/15

9:17 am-3:49 pm

1 stop5h 32m

White Plains Westchester County

Sat 6/20

12:38 pm-6:11 pm

1 stop6h 33m

$487

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 7/17

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Sun 7/19

6:29 am-11:56 am

1 stop6h 27m

$503

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 7/23

11:05 am-6:07 pm

1 stop6h 02m

White Plains Westchester County

Sun 7/26

6:29 am-11:56 am

1 stop6h 27m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/14

Showing 1-10 of 21 resultsSorted by cheapest first
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Compare providers for flights from Midway to White Plains

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Midway to White Plains in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Chicago Midway Airport-White Plains flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago Midway Airport-White Plains flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago Midway Airport-White Plains flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago Midway Airport-White Plains flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago Midway Airport-White Plains flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Midway to White Plains

Have a flexible travel schedule? Discover the best time to fly to White Plains from Midway 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.

Related info for your journey

Find useful and relevant information for your journey from Midway to White Plains. 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 White Plains from Chicago Midway?

    White Plains Westchester County (HPN), located 3.7 mi from the city center, is the airport you fly into when you book flights from Chicago Midway to White Plains. 0 airlines have flights to Westchester County from Chicago Midway on a regular basis. Booking flights from Chicago Midway to White Plains Westchester County should not be difficult; the airport handles an average of 0 inbound flights from Chicago Midway per day.

  • How long is the flight from Chicago Midway Airport to White Plains?

    Departing from Chicago Midway Airport to White Plains will take you 4h 58m. Airlines will cover a distance of 728 mi.

  • Can I find deals for flights from Midway to White Plains that include hotel bookings?

    Yes. In addition to deals on Midway to White Plains flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to White Plains?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to White Plains.

  • Can I find deals for business class flights from Midway to White Plains?

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

See more FAQs

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