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$158+ 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 11/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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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 September 11, 2025.

Round-trip from

$369
(Delta)

One-way from

$158
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$185
From White Plains Westchester County to Chicago Midway
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One-way flight from White Plains Westchester County to Chicago Midway
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Highest demand for flights based on searches. 4% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 11, 2025.

This Delta deal was found by Cheapflights users on 9/11. 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 10/2112:55 pmHPN - MDW
1 stop6h 30mDelta
Sat 10/2511:10 amMDW - HPN
1 stop3h 39mDelta
Deal found 9/11$369
This Delta deal was found by Cheapflights users on 9/9. 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 10/156:40 pmHPN - MDW
2 stops18h 48mDelta
Mon 10/206:23 pmMDW - HPN
1 stop16h 36mDelta
Deal found 9/9$370
This Delta deal was found by Cheapflights users on 9/9. 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 10/156:00 amHPN - MDW
2 stops13h 25mDelta
Wed 10/229:20 amMDW - HPN
1 stop6h 18mDelta
Deal found 9/9$372
This Delta deal was found by Cheapflights users on 9/9. 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 10/155:20 pmHPN - MDW
1 stop16h 20mDelta
Thu 10/239:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/9$398
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/114:29 pmHPN - MDW
1 stop6h 45mDelta
Tue 10/149:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/11$400
This Delta deal was found by Cheapflights users on 9/10. 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 11/812:55 pmHPN - MDW
1 stop6h 30mDelta
Sun 11/96:48 pmMDW - HPN
1 stop16h 19mDelta
Deal found 9/10$401
This Delta deal was found by Cheapflights users on 9/10. 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 9/2412:42 pmHPN - MDW
1 stop6h 53mDelta
Sat 9/276:00 amMDW - HPN
1 stop7h 29mDelta
Deal found 9/10$439
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 10/2412:55 pmHPN - MDW
1 stop6h 30mDelta
Tue 10/289:20 amMDW - HPN
1 stop6h 18mDelta
Deal found 9/11$469
This Delta deal was found by Cheapflights users on 9/10. 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 10/2412:55 pmHPN - MDW
1 stop6h 30mDelta
Mon 10/279:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/10$499
This Delta deal was found by Cheapflights users on 9/10. 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 9/124:29 pmHPN - MDW
1 stop6h 07mDelta
Sat 9/139:20 amMDW - HPN
1 stop6h 15mDelta
Deal found 9/10$511
This Delta deal was found by Cheapflights users on 9/11. 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.
Fri 9/124:29 pmHPN - MDW
1 stop6h 07mDelta
Mon 9/159:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/11$513
This Delta deal was found by Cheapflights users on 9/11. 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.
Sat 10/1112:55 pmHPN - MDW
1 stop6h 30mDelta
Sun 10/126:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/11$559

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 September 11, 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

Tue 10/21

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 10/25

11:10 am-3:49 pm

1 stop3h 39m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/15

6:40 pm-12:28 pm

2 stops18h 48m

Chicago Midway

Mon 10/20

6:23 pm-11:59 am

1 stop16h 36m

$370

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/15

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

Tue 10/21

6:23 pm-11:59 am

1 stop16h 36m

$370

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/15

6:00 am-6:25 pm

2 stops13h 25m

Chicago Midway

Wed 10/22

9:20 am-4:38 pm

1 stop6h 18m

$372

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/15

5:20 pm-8:40 am

1 stop16h 20m

Chicago Midway

Thu 10/23

9:35 am-3:49 pm

1 stop5h 14m

$398

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/25

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Mon 10/27

6:00 am-12:00 pm

1 stop5h 00m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 10/27

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Tue 11/4

6:00 am-12:00 pm

1 stop5h 00m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/11

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Tue 10/14

9:35 am-3:49 pm

1 stop5h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 9/24

12:42 pm-6:35 pm

1 stop6h 53m

Chicago Midway

Sat 9/27

6:00 am-2:29 pm

1 stop7h 29m

$439

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 10/24

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sun 10/26

9:20 am-4:38 pm

1 stop6h 18m

$499

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 20 results
1
2

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, April is the cheapest month in which you can book a flight from White Plains to Chicago Midway Airport (average of $160). Flying from White Plains to Chicago Midway Airport in November is currently the most expensive (average of $249). 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 30m. 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, April is the cheapest month in which you can book a flight from White Plains to Chicago Midway Airport (average of $160). Flying from White Plains to Chicago Midway Airport in November is currently the most expensive (average of $249). 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
Benton Harbor
Porter
Chesterton

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Alternative routes for White Plains to Midway

See prices for flight routes from nearby airports that may be better suited for you.
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