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Cheap flights from Westchester County to Midway (MDW) from $113

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 6/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
HPN — MDW
May 23 — May 301
From?
To?
Thu 5/23
Thu 5/30
1 adult, Economy
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How far in advance should I book a flight from Westchester County to Chicago Midway Airport?

To save on the cost of your flight from Westchester County to Chicago Midway Airport, book at least 56 days before your planned departure. Booking around this time can save you about 98% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $278 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $423.

What is the cheapest month to fly from Westchester County to Chicago Midway Airport?

The best pricing can be found in the month of February. Prices to Chicago Midway Airport from Westchester County average $261. You can even find prices in February for less than $261, as users have found deals to Chicago Midway Airport from as low as $81. The month of June appears to be one of the more expensive times to travel to Chicago Midway Airport from Westchester County. Flying in the targeted month can save you up to 33%.

When is the cheapest time to fly from Westchester County to Chicago Midway Airport (REU - MDW)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Chicago Midway Airport as you normally would.

Cheap Delta flights from Westchester County to Midway

Explore cheap flight options specifically provided by Delta for the route between Westchester County and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Peruse some of the lowest-priced Delta flights we've found from Westchester County to Chicago. Be sure to come back soon if the deals available don't appeal to you at this time.
Wed 8/283:15 pmHPN - MDW
1 stop7h 32mDelta
Sun 9/16:00 amMDW - HPN
1 stop5h 09mDelta
Deal found 5/18$345
Wed 8/144:25 pmHPN - MDW
1 stop6h 22mDelta
Thu 8/159:35 amMDW - HPN
1 stop5h 58mDelta
Deal found 5/17$370
Fri 8/2312:45 pmHPN - MDW
1 stop6h 14mDelta
Sun 8/256:00 amMDW - HPN
1 stop5h 09mDelta
Deal found 5/17$394
Tue 6/1812:30 pmHPN - MDW
1 stop5h 34mDelta
Tue 6/256:49 pmMDW - HPN
1 stop13h 43mDelta
Deal found 5/16$409
Fri 6/286:45 pmHPN - MDW
1 stop18h 10mDelta
Mon 7/19:29 amMDW - HPN
1 stop6h 16mDelta
Deal found 5/16$430
Sat 6/2912:30 pmHPN - MDW
1 stop5h 34mDelta
Tue 7/27:11 pmMDW - HPN
2 stops15h 36mDelta
Deal found 5/16$448
Sun 6/166:00 amHPN - MDW
1 stop16h 46mDelta
Tue 6/2512:45 pmMDW - HPN
1 stop8h 36mDelta
Deal found 5/16$449
Mon 6/1712:30 pmHPN - MDW
1 stop5h 34mDelta
Tue 6/2512:45 pmMDW - HPN
1 stop8h 36mDelta
Deal found 5/16$458
Thu 6/612:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 6/86:00 amMDW - HPN
1 stop15h 21mDelta
Deal found 5/18$459

Cheap WestJet flights from Westchester County to Midway

Explore cheap flight options specifically provided by WestJet for the route between Westchester County and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Some of the lowest-priced WestJet flights we've found at this time heading from Westchester County to Chicago. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Mon 6/175:25 pmHPN - MDW
3 stops26h 11mWestJet
Tue 6/252:24 pmMDW - HPN
3 stops20h 23mWestJet
Deal found 5/16$958
Thu 5/3012:45 pmHPN - MDW
3 stops25h 50mWestJet
Mon 6/39:46 amMDW - HPN
3 stops30h 03mWestJet
Deal found 5/16$1,202
Mon 6/175:25 pmHPN - MDW
3 stops26h 11mWestJet
Mon 6/242:24 pmMDW - HPN
3 stops20h 23mWestJet
Deal found 5/16$1,220
Mon 6/175:25 pmHPN - MDW
3 stops26h 11mWestJet
Sun 6/239:29 amMDW - HPN
3 stops25h 18mWestJet
Deal found 5/16$1,228

Cheap Westchester County to Midway flights in May & June 2024

Find cheap flight options from Westchester County to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Prices were last updated on May 18, 2024.
The lowest fares we've come across on flights traveling from Westchester County to Chicago in May and June 2024. More deals are always being added, so be sure to check back regularly.
Thu 6/612:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 6/86:00 amMDW - HPN
1 stop15h 21mDelta
Deal found 5/18$459
Sat 6/1512:30 pmHPN - MDW
1 stop5h 34mDelta
Sat 6/229:28 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$464
Thu 5/2312:45 pmHPN - MDW
1 stop5h 21mDelta
Sun 5/269:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$467
Fri 6/143:00 pmHPN - MDW
1 stop7h 46mDelta
Mon 6/173:45 pmMDW - HPN
1 stop5h 36mDelta
Deal found 5/18$484
Fri 6/143:00 pmHPN - MDW
1 stop7h 46mDelta
Sun 6/166:00 amMDW - HPN
1 stop5h 03mDelta
Deal found 5/18$523
Wed 6/54:20 pmHPN - MDW
1 stop6h 41mDelta
Fri 6/73:45 pmMDW - HPN
1 stop5h 36mDelta
Deal found 5/18$555
Mon 6/1712:30 pmHPN - MDW
1 stop5h 34mDelta
Mon 6/246:00 amMDW - HPN
1 stop5h 03mDelta
Deal found 5/18$562
Mon 6/1712:30 pmHPN - MDW
1 stop5h 34mDelta
Fri 6/219:34 amMDW - HPN
1 stop6h 11mDelta
Deal found 5/18$574
Fri 5/2412:45 pmHPN - MDW
1 stop5h 21mDelta
Tue 5/289:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$578

Westchester County to Midway 2024 flight deals

Discover exclusive flight deals for travel between Westchester County and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
The lowest fares we've come across on flights traveling from Westchester County to Chicago in May and June 2024. More deals are always being added, so be sure to check back regularly.
Wed 8/283:15 pmHPN - MDW
1 stop7h 32mDelta
Sun 9/16:00 amMDW - HPN
1 stop5h 09mDelta
Deal found 5/18$345
Fri 8/2312:45 pmHPN - MDW
1 stop6h 14mDelta
Sun 8/256:00 amMDW - HPN
1 stop5h 09mDelta
Deal found 5/18$394
Thu 6/612:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 6/86:00 amMDW - HPN
1 stop15h 21mDelta
Deal found 5/18$459
Sat 6/1512:30 pmHPN - MDW
1 stop5h 34mDelta
Sat 6/229:28 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$464
Thu 5/2312:45 pmHPN - MDW
1 stop5h 21mDelta
Sun 5/269:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$467
Thu 8/2912:30 pmHPN - MDW
1 stop5h 33mDelta
Sun 9/16:00 amMDW - HPN
1 stop5h 09mDelta
Deal found 5/18$474
Fri 6/143:00 pmHPN - MDW
1 stop7h 46mDelta
Mon 6/173:45 pmMDW - HPN
1 stop5h 36mDelta
Deal found 5/18$484
Thu 8/112:30 pmHPN - MDW
1 stop5h 34mDelta
Sat 8/33:47 pmMDW - HPN
1 stop5h 32mDelta
Deal found 5/18$513
Fri 6/143:00 pmHPN - MDW
1 stop7h 46mDelta
Sun 6/166:00 amMDW - HPN
1 stop5h 03mDelta
Deal found 5/18$523

Westchester County to Midway flights leaving soon

Find last-minute flight options from Westchester County to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Have a look at some of the last-minute flights available departing from Westchester County to Chicago. Users should examine the flight details to ensure there are no surprises.
Thu 5/2312:45 pmHPN - MDW
1 stop5h 21mDelta
Sun 5/269:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$467
Fri 5/2412:45 pmHPN - MDW
1 stop5h 21mDelta
Tue 5/289:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$578
Fri 5/2412:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 5/259:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$643
Fri 5/2412:45 pmHPN - MDW
1 stop5h 21mDelta
Mon 5/279:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$723
Sat 5/254:20 pmHPN - MDW
1 stop6h 41mDelta
Mon 5/279:32 amMDW - HPN
1 stop6h 17mDelta
Deal found 5/18$753

One-way flights to Midway from Westchester County

Search for one-way flight options from Westchester County to Midway. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
Users traveling one-way from Westchester County to Chicago can select one of these great deals. Those seeking round-trip flights from Westchester County to Chicago should utilize the search form at the the top of the page.
Sat 6/112:45 pmHPN - MDW
1 stop4h 28mDelta
Deal found 5/17$113
Mon 6/1012:30 pmHPN - MDW
1 stop5h 34mDelta
Deal found 5/17$287
Fri 5/2412:45 pmHPN - MDW
1 stop5h 21mDelta
Deal found 5/16$289
Fri 7/56:00 amHPN - MDW
1 stop4h 51mDelta
Deal found 5/18$359
Thu 5/3012:45 pmHPN - MDW
1 stop5h 21mDelta
Deal found 5/17$399
Thu 5/233:00 pmHPN - MDW
1 stop8h 01mDelta
Deal found 5/17$414
Sun 6/96:00 amHPN - MDW
1 stop4h 51mDelta
Deal found 5/18$459
Fri 7/55:20 pmHPN - MDW
3 stops26h 42mMultiple Airlines
Deal found 5/18$527
Wed 5/2912:45 pmHPN - MDW
3 stops25h 50mWestJet
Deal found 5/17$554

Find flights from Westchester County to Midway within your budget

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 2,634,509 searches. Data last updated May 18, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$345 - $958

Route

Depart

Return

Price

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 8/28

1 stop7h 32m

Chicago Midway

Sun 9/1

1 stop5h 09m

$345

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 8/14

1 stop6h 22m

Chicago Midway

Thu 8/15

1 stop5h 58m

$370

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 8/23

1 stop6h 14m

Chicago Midway

Sun 8/25

1 stop5h 09m

$394

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 6/18

1 stop5h 34m

Chicago Midway

Tue 6/25

1 stop13h 43m

$409

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 6/28

1 stop18h 10m

Chicago Midway

Mon 7/1

1 stop6h 16m

$430

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 6/29

1 stop5h 34m

Chicago Midway

Tue 7/2

2 stops15h 36m

$448

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Sun 6/16

1 stop16h 46m

Chicago Midway

Tue 6/25

1 stop8h 36m

$449

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 6/18

3 stops25h 32m

Chicago Midway

Fri 6/21

3 stops18h 32m

$894

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 6/17

3 stops26h 11m

Chicago Midway

Tue 6/25

3 stops20h 23m

$958

Flights are sorted by cheapest first

Deals found on 5/18

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 May 18, 2024.
Read reviews from past customers who have flown Delta and WestJet from Westchester County to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,647 reviews
Check prices

Food

7.4

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

8.0

Reviews

1 / 10

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

Delta
8.0
Very good
10,647 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Food

7.4

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

8.0

Reviews

1 / 10

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

WestJet
7.5
Good
2,899 reviews
Delta
8.0
Very good
10,647 reviews
Check prices

Food

7.4

Boarding

8.2

Comfort

7.9

Crew

8.6

Overall

8.0

Entertainment

8.0

Reviews

1 / 10

In the boarding area at La Guardia, there are charging stations for electronics but the electric outlets do not work on many of the stations.

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 flights from Westchester County to Chicago Midway Airport for under $400 on Cheapflights?

    Yes, there are multiple flights from Westchester County to Chicago Midway Airport for under $400. The cheapest flight booked recently is on Delta for just $345, but on average you can expect to pay $473.

  • Are there last-minute flights available from Westchester County to Chicago Midway Airport for under $500?

    There are currently 5+ open flights from Westchester County to Chicago Midway Airport within the next 7 days for less than $500.

  • What does HPN to MDW mean?

    This is defined as White Plains Westchester County Airport (HPN) and Chicago Midway Airport (MDW). Codes like Chicago Midway Airport are often used to just call airports uniquely.

  • Can I find deals for flights from Westchester County to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Westchester County to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Westchester County to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Westchester County to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Westchester County to Midway that allow pets onboard?

    Many airlines flying from Westchester County to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Westchester County to Midway?

    Yes, you can often find last-minute deals on Westchester County to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Westchester County to Chicago Midway Airport flight deals updated?

    The Westchester County to Chicago Midway Airport flight deals you see on this page were last updated on 5/18.

See more FAQs

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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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Top airline flying from Westchester County to Midway

Discover the top airline that operate flights from Westchester County to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,634,509 searches. Data last updated May 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$197Average$379FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
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Search flights from Westchester County to Midway by cabin class

Find flights from Westchester County to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Westchester County to Midway?

Cheapflights makes it easy to find Westchester County to Midway flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Westchester County to Midway?

Cheapflights simply makes it quick and affordable to book flights from Westchester County to Midway by bringing together all flight options from hundreds of airlines and agencies online — and put it in one place for you to choose from. Plus, Cheapflights is 100% free to use for all.

Can Cheapflights find flights from Westchester County to Midway with no change fees?

Need flexible booking options for your flight to Midway from Westchester County? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Westchester County to Midway become cheaper?

Of course! You can now track prices for flights from Westchester County to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

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