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Midway

$144+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
May 28 — Jun 41
Thu 5/28
Thu 6/4
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 April 28, 2026.

This Delta deal was found by Cheapflights users on 4/25. 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 6/1312:38 pm
HPN
-
MDW
1 stop6h 33m
Delta
Tue 6/166:00 am
MDW
-
HPN
1 stop5h 09m
Delta
Deal found 4/25$415
This Delta deal was found by Cheapflights users on 4/24. 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 5/2812:31 pm
HPN
-
MDW
1 stop7h 02m
Delta
Mon 6/19:22 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 4/24$449
This Delta deal was found by Cheapflights users on 4/25. 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 5/2312:31 pm
HPN
-
MDW
1 stop7h 02m
Delta
Sat 5/309:22 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 4/25$465
This Delta deal was found by Cheapflights users on 4/27. 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 5/206:00 am
HPN
-
MDW
1 stop6h 56m
Delta
Sat 5/239:22 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 4/27$475
This Delta deal was found by Cheapflights users on 4/23. 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 5/2912:31 pm
HPN
-
MDW
1 stop7h 02m
Delta
Mon 6/19:22 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 4/23$477
This Delta deal was found by Cheapflights users on 4/23. 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 7/112:35 pm
HPN
-
MDW
1 stop6h 56m
Delta
Fri 7/39:54 am
MDW
-
HPN
1 stop5h 36m
Delta
Deal found 4/23$481
This Delta deal was found by Cheapflights users on 4/23. 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 9/114:19 pm
HPN
-
MDW
1 stop6h 27m
Delta
Mon 9/146:00 am
MDW
-
HPN
1 stop7h 32m
Delta
Deal found 4/23$483
This Delta deal was found by Cheapflights users on 4/27. 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 4/306:00 am
HPN
-
MDW
1 stop7h 07m
Delta
Sat 5/211:18 am
MDW
-
HPN
1 stop5h 58m
Delta
Deal found 4/27$509
This Delta deal was found by Cheapflights users on 4/23. 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 7/3112:35 pm
HPN
-
MDW
1 stop6h 50m
Delta
Sun 8/29:20 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 4/23$511
This Delta deal was found by Cheapflights users on 4/27. 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 5/214:29 pm
HPN
-
MDW
1 stop5h 40m
Delta
Thu 5/286:23 am
MDW
-
HPN
1 stop7h 06m
Delta
Deal found 4/27$513
This Delta deal was found by Cheapflights users on 4/23. 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 5/294:29 pm
HPN
-
MDW
1 stop5h 40m
Delta
Sun 5/316:23 am
MDW
-
HPN
1 stop7h 06m
Delta
Deal found 4/23$517

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 April 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$415
(Delta)

One-way from

$144
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$278
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. 11% potential increase in price ($30 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 April 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 April 28, 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

Wed 5/20

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Sat 5/23

9:22 am-3:49 pm

1 stop5h 27m

$475

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 7/1

12:35 pm-6:31 pm

1 stop6h 56m

Chicago Midway

Fri 7/3

9:54 am-4:30 pm

1 stop5h 36m

$481

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 9/11

4:19 pm-9:46 pm

1 stop6h 27m

Chicago Midway

Mon 9/14

6:00 am-2:32 pm

1 stop7h 32m

$483

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/24

4:29 pm-10:15 pm

1 stop6h 46m

Chicago Midway

Sun 7/26

9:19 am-3:47 pm

1 stop5h 28m

$483
Quickest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/31

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Mon 8/3

6:05 am-12:08 pm

1 stop5h 03m

$483

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 7/30

10:29 am-4:15 pm

1 stop6h 46m

Chicago Midway

Sun 8/2

9:19 am-3:47 pm

1 stop5h 28m

$511

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/10

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Sun 7/12

9:19 am-3:47 pm

1 stop5h 28m

$511

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 7/31

12:36 pm-6:25 pm

1 stop6h 49m

Chicago Midway

Sun 8/2

9:19 am-3:47 pm

1 stop5h 28m

$511
Cheapest one-way

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/27

12:00 pm-10:02 pm

2 stops35h 02m

$151

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sun 6/28

8:00 am-11:09 am

2 stops28h 09m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 20 resultsSorted by cheapest first
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 April.
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 6h 56m. 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
Hammond
Porter

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