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$135+ Cheap flights from Westchester County 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
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 September 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$369
(Delta)

One-way from

$135
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$218
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From Westchester County to Chicago Midway
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One-way flight from Westchester County to Chicago Midway
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Highest demand for flights based on searches. 7% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 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 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 September 25, 2025.

This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 11/812:55 pmHPN - MDW
1 stop6h 30mDelta
Sat 11/156:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/23$369
This Delta deal was found by Cheapflights users on 9/24. 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 10/2512:55 pmHPN - MDW
1 stop6h 30mDelta
Mon 10/279:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/24$400
This Delta deal was found by Cheapflights users on 9/23. 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.
Tue 10/2112:55 pmHPN - MDW
1 stop6h 30mDelta
Sat 10/259:20 amMDW - HPN
1 stop6h 18mDelta
Deal found 9/23$404
This Delta deal was found by Cheapflights users on 9/23. 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 10/2412:55 pmHPN - MDW
1 stop6h 30mDelta
Mon 10/279:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/23$431
This Delta deal was found by Cheapflights users on 9/22. 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 10/2712:55 pmHPN - MDW
1 stop6h 30mDelta
Tue 11/410:40 amMDW - HPN
1 stop6h 20mDelta
Deal found 9/22$469
This Delta deal was found by Cheapflights users on 9/25. 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.
Thu 11/136:00 amHPN - MDW
1 stop6h 52mDelta
Sun 11/166:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/25$499
This Delta deal was found by Cheapflights users on 9/23. 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.
Sat 10/1112:55 pmHPN - MDW
1 stop6h 30mDelta
Tue 10/149:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/23$511
This Delta deal was found by Cheapflights users on 9/25. 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.
Thu 9/256:00 amHPN - MDW
1 stop6h 48mDelta
Mon 9/296:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/25$513
This Delta deal was found by Cheapflights users on 9/24. 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 10/313:15 pmHPN - MDW
1 stop7h 59mDelta
Sun 11/25:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 9/24$523
This Delta deal was found by Cheapflights users on 9/24. 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.
Wed 10/2912:55 pmHPN - MDW
1 stop6h 30mDelta
Fri 10/319:35 amMDW - HPN
1 stop5h 55mDelta
Deal found 9/24$527
This KAYAK deal was found by Cheapflights users on 9/24. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:55 pmHPN - MDW
1 stop6h 30mDelta
Thu 10/169:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 9/24$537

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 September 25, 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

Wed 11/12

6:41 pm-11:40 pm

1 stop5h 59m

Chicago Midway

Tue 11/18

6:00 am-12:00 pm

1 stop5h 00m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 11/8

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 11/15

6:00 am-12:00 pm

1 stop5h 00m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 1/10

12:45 pm-6:34 pm

1 stop6h 49m

Chicago Midway

Sun 1/11

9:20 am-4:40 pm

1 stop6h 20m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 11/11

4:29 pm-11:40 pm

1 stop8h 11m

Chicago Midway

Mon 11/17

9:34 am-3:49 pm

1 stop5h 15m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 1/17

4:19 pm-9:46 pm

1 stop6h 27m

Chicago Midway

Sun 1/18

6:00 am-12:11 pm

1 stop5h 11m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/25

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Mon 10/27

9:35 am-3:49 pm

1 stop5h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

12:55 pm-6:06 pm

1 stop6h 11m

Chicago Midway

Mon 12/15

6:00 am-11:59 am

1 stop4h 59m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 11/12

6:41 pm-11:40 pm

1 stop5h 59m

Chicago Midway

Mon 11/17

10:47 am-6:01 pm

1 stop6h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 10/15

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Wed 10/29

10:40 am-6:00 pm

1 stop6h 20m

$404

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

9:20 am-4:38 pm

1 stop6h 18m

$404

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 19 results
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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.

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.

  • How long is the flight from Westchester County to Chicago Midway Airport?

    Airlines like Delta fly from Westchester County to Chicago Midway Airport in about 5h 59m. The time it takes to get you to your destination can typically vary by up to . The distance from Westchester County to Chicago Midway Airport is about 728 mi.

  • 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
Chesterton

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Alternative routes for Westchester County to Midway

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