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$103+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — HPN
Dec 25 — Jan 11
Thu 12/25
Thu 1/1
1 adult, Economy
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Cheap 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 November 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$369
(Delta)

One-way from

$103
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$217
Provider with most accurate pricing for Chicago Midway-White Plains Westchester County flight deals.
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Provider most trusted by Cheapflights users for Chicago Midway-White Plains Westchester County flights.
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From Chicago Midway to White Plains Westchester County
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One-way flight from Chicago Midway to White Plains Westchester County
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Highest demand for flights based on searches. 5% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find 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 November 25, 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.
Tue 11/256:00 amMDW - HPN
1 stop5h 00mDelta
Tue 12/24:29 pmHPN - MDW
1 stop8h 18mDelta
Deal found 11/24$469
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 12/56:00 amMDW - HPN
1 stop7h 28mDelta
Sat 12/66:50 pmHPN - MDW
1 stop5h 57mDelta
Deal found 11/24$506
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.
Sat 12/209:29 amMDW - HPN
1 stop5h 20mDelta
Sat 1/176:00 amHPN - MDW
1 stop5h 32mDelta
Deal found 11/25$529
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 12/56:00 amMDW - HPN
1 stop5h 00mDelta
Sun 12/712:55 pmHPN - MDW
1 stop6h 05mDelta
Deal found 11/25$543
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.
Thu 11/276:00 amMDW - HPN
1 stop5h 00mDelta
Fri 11/284:29 pmHPN - MDW
1 stop8h 11mDelta
Deal found 11/24$569
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.
Sat 12/209:29 amMDW - HPN
1 stop5h 20mDelta
Tue 12/3012:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/24$600
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.
Sat 12/279:29 amMDW - HPN
1 stop5h 20mDelta
Tue 12/3012:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/24$620
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 11/286:00 amMDW - HPN
1 stop5h 00mDelta
Fri 11/284:29 pmHPN - MDW
1 stop8h 11mDelta
Deal found 11/25$656
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 12/269:29 amMDW - HPN
1 stop5h 20mDelta
Mon 12/2912:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/24$699
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.
Sat 12/209:29 amMDW - HPN
1 stop5h 20mDelta
Fri 12/266:03 amHPN - MDW
1 stop6h 55mDelta
Deal found 11/25$719
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 12/196:00 amMDW - HPN
1 stop5h 00mDelta
Tue 12/2312:55 pmHPN - MDW
1 stop5h 31mDelta
Deal found 11/24$761
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.
Sat 12/139:59 amMDW - HPN
1 stop5h 38mDelta
Tue 12/1612:55 pmHPN - MDW
1 stop6h 05mDelta
Deal found 11/24$779

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 November 25, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to White Plains that are best for you.

Fly from

Midway

Fly to

White Plains

Route

Depart

Return

Price

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 1/7

9:50 am-4:32 pm

1 stop5h 42m

White Plains Westchester County

Wed 1/14

4:29 pm-10:07 pm

1 stop6h 38m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 1/28

6:00 am-12:06 pm

1 stop5h 06m

White Plains Westchester County

Sat 1/31

5:15 pm-10:22 pm

1 stop6h 07m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 1/20

6:35 pm-11:56 am

1 stop16h 21m

White Plains Westchester County

Thu 1/29

12:59 pm-5:29 pm

1 stop5h 30m

$392

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 1/21

9:32 am-3:49 pm

1 stop5h 17m

White Plains Westchester County

Thu 1/29

12:59 pm-5:29 pm

1 stop5h 30m

$400

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 1/24

6:25 am-2:26 pm

1 stop7h 01m

White Plains Westchester County

Thu 1/29

12:36 pm-5:55 pm

1 stop6h 19m

$400

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 1/22

10:48 am-10:00 pm

1 stop10h 12m

White Plains Westchester County

Thu 1/29

6:00 am-11:59 am

1 stop6h 59m

$407

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 1/8

11:21 am-6:00 pm

1 stop5h 39m

White Plains Westchester County

Mon 1/12

12:36 pm-5:34 pm

1 stop5h 58m

$431

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 12/13

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Mon 12/15

6:10 am-11:55 am

1 stop6h 45m

$506

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 12/5

6:00 am-2:28 pm

1 stop7h 28m

White Plains Westchester County

Sat 12/6

6:50 pm-11:47 pm

1 stop5h 57m

$506

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Mon 12/15

3:10 pm-11:29 am

2 stops19h 19m

$103

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/24

Showing 1-10 of 19 results
1
2

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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago Midway Airport-White Plains flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to White Plains

What is the cheapest month to book a flight from Chicago Midway Airport to White Plains?

Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to White Plains (average of $44). Flying from Chicago Midway Airport to White Plains in August is currently the most expensive (average of $227). 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 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 5h 42m. 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to White Plains?

    Currently, October is the cheapest month in which you can book a flight from Chicago Midway Airport to White Plains (average of $44). Flying from Chicago Midway Airport to White Plains in August is currently the most expensive (average of $227). 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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