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Midway

$172+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap 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 July 27, 2026.

This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/512:36 pm
HPN
-
MDW
1 stop5h 23m
Delta
Sun 9/66:05 am
MDW
-
HPN
1 stop4h 58m
Delta
Deal found 7/27$407
This Delta deal was found by Cheapflights users on 7/27. 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.
Thu 8/612:36 pm
HPN
-
MDW
1 stop6h 57m
Delta
Sat 8/86:11 am
MDW
-
HPN
1 stop4h 52m
Delta
Deal found 7/27$417
This Delta deal was found by Cheapflights users on 7/24. 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 7/2512:36 pm
HPN
-
MDW
1 stop6h 31m
Delta
Mon 7/279:19 am
MDW
-
HPN
1 stop5h 28m
Delta
Deal found 7/24$427
This Delta deal was found by Cheapflights users on 7/27. 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 9/116:40 pm
HPN
-
MDW
1 stop5h 04m
Delta
Mon 9/146:05 am
MDW
-
HPN
1 stop4h 58m
Delta
Deal found 7/27$443
This Delta deal was found by Cheapflights users on 7/27. 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 8/712:36 pm
HPN
-
MDW
1 stop6h 57m
Delta
Fri 8/146:05 am
MDW
-
HPN
1 stop4h 58m
Delta
Deal found 7/27$453
This Delta deal was found by Cheapflights users on 7/27. 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.
Wed 7/2912:36 pm
HPN
-
MDW
1 stop6h 49m
Delta
Wed 8/59:24 am
MDW
-
HPN
1 stop5h 24m
Delta
Deal found 7/27$460
This Delta deal was found by Cheapflights users on 7/24. 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 7/314:29 pm
HPN
-
MDW
1 stop6h 46m
Delta
Sun 8/29:19 am
MDW
-
HPN
1 stop5h 28m
Delta
Deal found 7/24$463
This Delta deal was found by Cheapflights users on 7/24. 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 8/112:36 pm
HPN
-
MDW
1 stop6h 31m
Delta
Wed 8/56:05 am
MDW
-
HPN
1 stop7h 24m
Delta
Deal found 7/24$470
This Delta deal was found by Cheapflights users on 7/26. 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.
Wed 7/2912:36 pm
HPN
-
MDW
1 stop6h 49m
Delta
Sat 8/16:00 am
MDW
-
HPN
1 stop5h 08m
Delta
Deal found 7/26$496
This Delta deal was found by Cheapflights users on 7/27. 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 9/186:40 pm
HPN
-
MDW
1 stop5h 04m
Delta
Wed 9/236:05 am
MDW
-
HPN
1 stop4h 58m
Delta
Deal found 7/27$500
This Delta deal was found by Cheapflights users on 7/24. 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 9/36:00 am
HPN
-
MDW
1 stop6h 51m
Delta
Sat 9/59:24 am
MDW
-
HPN
1 stop5h 24m
Delta
Deal found 7/24$510

Find 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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$407
(Delta)

One-way from

$172
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$310
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. 17% potential increase in price ($53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 July 27, 2026.
Use the filters below to find and compare flights from White Plains to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 10/30

6:00 am-10:03 am

1 stop5h 03m

Chicago Midway

Sun 11/1

10:01 am-4:42 pm

1 stop5h 41m

$453

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/11

12:30 pm-6:04 pm

1 stop6h 34m

Chicago Midway

Sun 12/13

10:22 am-4:34 pm

1 stop5h 12m

$453

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/11

12:30 pm-6:04 pm

1 stop6h 34m

Chicago Midway

Thu 12/31

9:30 am-4:33 pm

1 stop6h 03m

$453

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 8/7

12:36 pm-6:33 pm

1 stop6h 57m

Chicago Midway

Mon 8/10

9:24 am-3:48 pm

1 stop5h 24m

$453

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 9/4

12:36 pm-6:33 pm

1 stop6h 57m

Chicago Midway

Sun 9/6

6:05 am-12:03 pm

1 stop4h 58m

$536

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 8/13

6:00 am-11:51 am

1 stop6h 51m

Chicago Midway

Mon 8/17

9:24 am-3:48 pm

1 stop5h 24m

$536

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 11/6

4:27 pm-10:25 pm

1 stop6h 58m

Chicago Midway

Sun 11/8

9:59 am-4:42 pm

1 stop5h 43m

$546
Quickest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 9/18

6:40 pm-10:44 pm

1 stop5h 04m

Chicago Midway

Sun 9/20

6:05 am-12:03 pm

1 stop4h 58m

$609

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 11/13

12:30 pm-6:04 pm

1 stop6h 34m

Chicago Midway

Sun 11/15

1:22 pm-10:19 pm

2 stops7h 57m

$671
Cheapest one-way

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 9/1

1:29 pm-10:55 am

2 stops22h 26m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3

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 July.
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 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.

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 5h 03m. 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.

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
Benton Harbor
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

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