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$136+ Cheap flights from White Plains (HPN) to Midway (MDW)

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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Nov 19 — Nov 261
Wed 11/19
Wed 11/26
1 adult, Economy
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Find flight deals from White Plains to Midway

Cheapest flights from White Plains to Midway
Explore the most affordable flight options available from White Plains to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 20, 2025.

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.
Thu 12/1812:55 pmHPN - MDW
1 stop6h 05mDelta
Tue 12/239:29 amMDW - HPN
1 stop5h 20mDelta
Deal found 10/19$400
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.
Tue 10/214:29 pmHPN - MDW
1 stop6h 45mDelta
Sat 10/2510:35 amMDW - HPN
1 stop6h 25mDelta
Deal found 10/19$439
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.
Fri 10/313:15 pmHPN - MDW
1 stop7h 59mDelta
Mon 11/39:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 10/20$441
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 10/254:29 pmHPN - MDW
1 stop6h 45mDelta
Mon 10/276:00 amMDW - HPN
1 stop7h 29mDelta
Deal found 10/19$476
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 10/246:00 amHPN - MDW
1 stop6h 53mDelta
Mon 10/276:00 amMDW - HPN
1 stop7h 29mDelta
Deal found 10/19$513
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.
Wed 12/246:03 amHPN - MDW
1 stop9h 41mDelta
Mon 12/296:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 10/20$557
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.
Fri 11/216:41 pmHPN - MDW
1 stop5h 59mDelta
Sun 11/239:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 10/20$590
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.
Mon 10/274:29 pmHPN - MDW
1 stop6h 45mDelta
Tue 11/49:20 amMDW - HPN
1 stop6h 18mDelta
Deal found 10/19$594
This Delta deal was found by Cheapflights users on 10/18. 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 11/2512:55 pmHPN - MDW
1 stop6h 13mDelta
Sat 11/296:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 10/18$604
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.
Fri 11/74:29 pmHPN - MDW
1 stop6h 45mDelta
Sun 11/99:41 amMDW - HPN
1 stop5h 53mDelta
Deal found 10/20$631
This Delta deal was found by Cheapflights users on 10/18. 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 11/112:55 pmHPN - MDW
1 stop6h 00mDelta
Sun 11/29:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 10/18$644
This Delta deal was found by Cheapflights users on 10/17. 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 12/312:55 pmHPN - MDW
1 stop6h 05mDelta
Sat 12/66:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 10/17$679

Cheap flight deals from White Plains to Midway

Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) to Midway (MDW). 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 October 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$400
(Delta)

One-way from

$136
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$241
Provider with most accurate pricing for White Plains Westchester County-Chicago Midway flight deals.
Search Deals
Provider most trusted by Cheapflights users for White Plains Westchester County-Chicago Midway flights.
Search Deals
From White Plains Westchester County to Chicago Midway
Search Deals
One-way flight from White Plains Westchester County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 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 White Plains to Midway 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 20, 2025.
Use the filters below to find and compare flights from White Plains to Chicago Midway Airport that are best for you.

Fly from

White Plains

Fly to

Midway

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 4/8

12:45 pm-6:34 pm

1 stop6h 49m

Chicago Midway

Sun 4/12

9:20 am-4:40 pm

1 stop6h 20m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/18

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Tue 12/23

9:29 am-3:49 pm

1 stop5h 20m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 11/5

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Wed 11/12

10:47 am-6:01 pm

1 stop6h 14m

$439

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 11/4

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 11/8

9:20 am-4:38 pm

1 stop6h 18m

$439

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 10/31

3:15 pm-10:14 pm

1 stop7h 59m

Chicago Midway

Mon 11/3

9:35 am-3:49 pm

1 stop5h 14m

$441

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 11/7

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Sat 11/8

10:35 am-6:00 pm

1 stop6h 25m

$476

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 11/8

5:20 pm-10:14 pm

1 stop5h 54m

Chicago Midway

Mon 11/10

9:34 am-3:49 pm

1 stop5h 15m

$476

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 11/14

12:55 pm-6:08 pm

1 stop6h 13m

Chicago Midway

Mon 11/17

6:00 am-12:00 pm

1 stop5h 00m

$513

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/25

6:03 am-10:22 pm

1 stop17h 19m

Chicago Midway

Mon 12/29

6:00 am-12:00 pm

1 stop5h 00m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/18

Showing 1-10 of 20 results
1
2

Compare providers for flights from White Plains to Midway

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 White Plains to Midway in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 White Plains-Chicago Midway Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Chicago Midway Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from White Plains-Chicago Midway Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on White Plains-Chicago Midway Airport 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 White Plains-Chicago Midway Airport 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 White Plains to Midway

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

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

Currently, November is the cheapest month in which you can book a flight from White Plains to Chicago Midway Airport (average of $54). Flying from White Plains to Chicago Midway Airport in August is currently the most expensive (average of $194). 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 White Plains to Midway. 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 from for flights from White Plains to Chicago Midway?

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

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

    Airlines like Delta fly from White Plains to Chicago Midway Airport in about 6h 49m. The time it takes to get you to your destination can typically vary by up to . There are 728 mi between White Plains and Chicago Midway Airport.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from White Plains to Midway 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 White Plains to Chicago Midway Airport?

    Currently, November is the cheapest month in which you can book a flight from White Plains to Chicago Midway Airport (average of $54). Flying from White Plains to Chicago Midway Airport in August is currently the most expensive (average of $194). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Porter
Benton Harbor
Chesterton

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