HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$124+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — MDW
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Westchester County to Midway with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 January 8, 2026.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$347
(Delta)

One-way from

$124
(Kiwi.com)

Popular in

August

Cheapest in

January

Average price

$179
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
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. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 8, 2026.

This Delta deal was found by Cheapflights users on 1/6. 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 1/124:29 pmHPN - MDW
1 stop6h 38mDelta
Mon 1/199:32 amMDW - HPN
1 stop5h 17mDelta
Deal found 1/6$347
This Delta deal was found by Cheapflights users on 1/7. 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 4/412:35 pmHPN - MDW
1 stop6h 19mDelta
Wed 4/89:35 amMDW - HPN
1 stop5h 14mDelta
Deal found 1/7$355
This Delta deal was found by Cheapflights users on 1/7. 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 2/312:38 pmHPN - MDW
1 stop6h 17mDelta
Tue 2/109:33 amMDW - HPN
1 stop5h 16mDelta
Deal found 1/7$385
This Delta deal was found by Cheapflights users on 1/6. 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 3/1212:35 pmHPN - MDW
1 stop6h 19mDelta
Sat 3/1410:45 amMDW - HPN
1 stop6h 33mDelta
Deal found 1/6$389
This Delta deal was found by Cheapflights users on 1/6. 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 1/2712:59 pmHPN - MDW
1 stop5h 30mDelta
Tue 2/39:53 amMDW - HPN
1 stop5h 39mDelta
Deal found 1/6$415
This Delta deal was found by Cheapflights users on 1/6. 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 4/115:15 pmHPN - MDW
1 stop6h 16mDelta
Sun 4/129:30 amMDW - HPN
1 stop6h 07mDelta
Deal found 1/6$419
This Delta deal was found by Cheapflights users on 1/7. 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 4/104:29 pmHPN - MDW
1 stop7h 02mDelta
Fri 4/176:30 amMDW - HPN
1 stop6h 59mDelta
Deal found 1/7$423
This Delta deal was found by Cheapflights users on 1/7. 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 5/2312:45 pmHPN - MDW
1 stop6h 46mDelta
Mon 5/256:00 amMDW - HPN
1 stop5h 14mDelta
Deal found 1/7$447
This Delta deal was found by Cheapflights users on 1/8. 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 1/315:15 pmHPN - MDW
1 stop6h 07mDelta
Mon 2/26:00 amMDW - HPN
1 stop7h 25mDelta
Deal found 1/8$449
This Delta deal was found by Cheapflights users on 1/7. 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 2/2012:56 pmHPN - MDW
1 stop5h 49mDelta
Sun 2/229:34 amMDW - HPN
1 stop5h 15mDelta
Deal found 1/7$451
This Delta deal was found by Cheapflights users on 1/6. 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 amHPN - MDW
1 stop7h 07mDelta
Sun 5/106:00 amMDW - HPN
1 stop5h 14mDelta
Deal found 1/6$461
This Delta deal was found by Cheapflights users on 1/6. 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 1/1612:36 pmHPN - MDW
1 stop6h 01mDelta
Mon 1/196:00 amMDW - HPN
1 stop5h 06mDelta
Deal found 1/6$467

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 January 8, 2026.
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

Mon 1/26

12:59 pm-5:29 pm

1 stop5h 30m

Chicago Midway

Wed 1/28

6:00 am-12:06 pm

1 stop5h 06m

$347

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 1/28

10:29 am-5:29 pm

1 stop8h 00m

Chicago Midway

Thu 1/29

10:48 am-6:00 pm

1 stop6h 12m

$347

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 4/8

12:48 pm-4:55 pm

1 stop5h 07m

Chicago Midway

Sat 4/11

9:30 am-4:35 pm

1 stop6h 05m

$347

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 3/13

4:29 pm-10:31 pm

1 stop7h 02m

Chicago Midway

Sun 3/15

9:35 am-3:49 pm

1 stop5h 14m

$347

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/4

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

Wed 4/8

9:35 am-3:49 pm

1 stop5h 14m

$355

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 2/3

12:38 pm-5:55 pm

1 stop6h 17m

Chicago Midway

Tue 2/10

9:33 am-3:49 pm

1 stop5h 16m

$385

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/11

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

Sat 4/18

6:30 am-2:29 pm

1 stop6h 59m

$385

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 3/11

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

Sun 3/15

9:35 am-3:49 pm

1 stop5h 14m

$389

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 4/22

10:27 am-4:36 pm

1 stop7h 09m

Chicago Midway

Sun 4/26

9:26 am-4:32 pm

1 stop6h 06m

$389

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 2/19

10:28 am-5:45 pm

1 stop8h 17m

Chicago Midway

Tue 2/24

9:50 am-4:32 pm

1 stop5h 42m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/7

Showing 1-10 of 24 results
1
2
3

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 30m. 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Westchester County to Midway

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to Midway flights
Newark to Midway flights
LaGuardia to Midway flights
Buffalo to O'Hare Intl flights
Syracuse to O'Hare Intl flights
Rochester to O'Hare Intl flights
Albany to O'Hare Intl flights
White Plains to O'Hare Intl flights
Albany to Midway flights
Buffalo to Midway flights
Rochester to Midway flights
Syracuse to Midway flights
Stewart to O'Hare Intl flights
White Plains to Midway flights
Islip to O'Hare Intl flights
Ithaca to O'Hare Intl flights
Elmira to O'Hare Intl flights
Ithaca to Midway flights
Elmira to Midway flights
Binghamton to O'Hare Intl flights
Watertown to O'Hare Intl flights
Binghamton to Midway flights
Plattsburgh to O'Hare Intl flights
Rutland to O'Hare Intl flights
Newark to Rockford flights
Saranac Lake to O'Hare Intl flights
Stewart to Midway flights
Stewart to Rockford flights
Niagara Falls to O'Hare Intl flights

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.