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$141+ 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
Dec 17 — Dec 241
Wed 12/17
Wed 12/24
1 adult, Economy
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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 November 17, 2025.

This Delta deal was found by Cheapflights users on 11/16. 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 12/1912:55 pmHPN - MDW
1 stop6h 05mDelta
Sun 12/219:29 amMDW - HPN
1 stop5h 20mDelta
Deal found 11/16$431
This Delta deal was found by Cheapflights users on 11/16. 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 11/186:41 pmHPN - MDW
1 stop5h 59mDelta
Sat 11/229:41 amMDW - HPN
1 stop5h 53mDelta
Deal found 11/16$469
This Delta deal was found by Cheapflights users on 11/17. 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 12/114:29 pmHPN - MDW
1 stop8h 18mDelta
Thu 12/189:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 11/17$487
This Delta deal was found by Cheapflights users on 11/15. 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 11/155:20 pmHPN - MDW
1 stop7h 20mDelta
Sun 11/169:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 11/15$506
This Delta deal was found by Cheapflights users on 11/15. 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 12/1912:55 pmHPN - MDW
1 stop6h 05mDelta
Tue 12/239:29 amMDW - HPN
1 stop5h 20mDelta
Deal found 11/15$530
This Delta deal was found by Cheapflights users on 11/17. 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 11/2112:55 pmHPN - MDW
1 stop6h 19mDelta
Sun 11/239:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 11/17$543
This Delta deal was found by Cheapflights users on 11/16. 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 12/164:29 pmHPN - MDW
1 stop8h 18mDelta
Tue 12/239:29 amMDW - HPN
1 stop5h 20mDelta
Deal found 11/16$559
This Delta deal was found by Cheapflights users on 11/15. 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 11/266:41 pmHPN - MDW
1 stop5h 59mDelta
Thu 11/276:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 11/15$569
This Delta deal was found by Cheapflights users on 11/15. 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 12/1912:55 pmHPN - MDW
1 stop6h 05mDelta
Wed 12/243:29 pmMDW - HPN
1 stop5h 40mDelta
Deal found 11/15$640
This Delta deal was found by Cheapflights users on 11/15. 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 11/266:41 pmHPN - MDW
1 stop5h 59mDelta
Fri 11/286:00 amMDW - HPN
1 stop7h 28mDelta
Deal found 11/15$656
This KAYAK deal was found by Cheapflights users on 11/17. 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.
Tue 12/26:10 amHPN - MDW
1 stop6h 45mDelta
Wed 12/36:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 11/17$694

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 November 17, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$400
(Delta)

One-way from

$141
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$235
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
Search Deals
One-way flight from Westchester County to Chicago Midway
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
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 November 2025
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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 November 17, 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

Sat 1/17

5:15 pm-10:07 pm

1 stop5h 52m

Chicago Midway

Mon 1/19

10:46 am-6:00 pm

1 stop6h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 1/9

12:36 pm-5:37 pm

1 stop6h 01m

Chicago Midway

Tue 1/13

11:21 am-6:00 pm

1 stop5h 39m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 3/6

12:59 pm-5:45 pm

1 stop5h 46m

Chicago Midway

Sun 3/8

6:00 am-12:11 pm

1 stop5h 11m

$431

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 1/8

4:29 pm-10:07 pm

1 stop6h 38m

Chicago Midway

Mon 1/12

9:50 am-4:32 pm

1 stop5h 42m

$431

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/19

12:55 pm-6:00 pm

1 stop6h 05m

Chicago Midway

Sun 12/21

9:29 am-3:49 pm

1 stop5h 20m

$431

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/2

4:19 pm-9:45 pm

1 stop6h 26m

Chicago Midway

Tue 5/5

9:30 am-12:14 pm

2 stops25h 44m

$435

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/6

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Tue 12/9

9:34 am-3:49 pm

1 stop5h 15m

$469

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 12/11

4:29 pm-11:47 pm

1 stop8h 18m

Chicago Midway

Thu 12/18

9:34 am-3:49 pm

1 stop5h 15m

$487

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 12/12

6:50 pm-11:47 pm

1 stop5h 57m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$487

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

12:55 pm-6:06 pm

1 stop6h 11m

Chicago Midway

Sun 12/14

6:00 am-12:00 pm

1 stop5h 00m

$506

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

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 52m. 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.

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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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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