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$353+ Cheap flights from Westchester County to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Aug 6 — Aug 131
Wed 8/6
Wed 8/13
1 adult, Economy
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Cheap flight deals from Westchester County to Midway

Keep the following information in mind while searching for Westchester County to Midway flight deals. Data was last updated August 1, 2025.

Round-trip from

$353
(Delta)

Popular in

June

Cheapest in

September

Average price

$241
From Westchester County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
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Find flight deals from Westchester County to Midway

Cheapest flights from Westchester County to Midway
Explore the most affordable flight options available from Westchester County to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 1, 2025.

This Delta deal was found by Cheapflights users on 7/30. 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 10/1812:55 pmHPN - MDW
1 stop6h 30mDelta
Tue 10/219:35 amMDW - HPN
2 stops11h 34mDelta
Deal found 7/30$353

Cheapflights Fare Finder

 
Customize your flight search to find flights from Westchester County 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 August 1, 2025.
Use the filters below to find and compare flights from Westchester County to Chicago Midway Airport that are best for you.

Fly from

Westchester County

Fly to

Midway

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sun 8/31

3:10 pm-9:12 pm

1 stop7h 02m

Chicago Midway

Sat 9/6

9:31 am-3:49 pm

1 stop5h 18m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 8/19

12:37 pm-6:37 pm

1 stop7h 00m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/1

Best time to book a flight from Westchester County to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Westchester County 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 Westchester County to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated August 1, 2025.
See what other customers who have flown with Delta from Westchester County to Chicago Midway Airport have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,983 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,983 reviews
Delta
8.0
Very good
7,983 reviews

Food

7.3

Entertainment

7.9

Overall

8.0

Comfort

7.9

Crew

8.5

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from Westchester County to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Westchester County to Midway that include hotel bookings?

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

  • How can I find direct flights from Westchester County to Midway?

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

  • Can I find deals for business class flights from Westchester County to Midway?

    Yes. Cheapflights offers flight deals from Westchester County 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 Westchester County to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Westchester County to Chicago Midway Airport (average of $160). Flying from Westchester County 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
Valparaiso
Chesterton

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