Cheap flights from Westchester County to Midway (MDW) from $121

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 5/17. 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
Apr 3 — Apr 101

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 48 days before your planned departure. Booking around this time can save you about 76% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $302 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $415.

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 $268. You can even find prices in February for less than $268, as users have found deals to Chicago Midway Airport from as low as $107. 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 34%.

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 3,228,805 searches. Data last updated March 29, 2024.
Wed 5/16:10 amHPN - MDW
1 stop17h 04mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/27$344
Wed 5/16:10 amHPN - MDW
1 stop17h 04mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/28$365
Wed 5/15:50 amHPN - MDW
2 stops17h 24mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/27$370
Wed 5/15:50 amHPN - MDW
2 stops17h 24mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/28$391
Wed 5/15:50 amHPN - MDW
2 stops11h 20mDelta
Sat 5/49:30 amMDW - HPN
2 stops10h 59mDelta
Deal found 3/27$425
Wed 5/15:50 amHPN - MDW
2 stops12h 30mDelta
Sat 5/49:30 amMDW - HPN
2 stops10h 59mDelta
Deal found 3/28$440
Tue 5/1412:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 5/186:00 amMDW - HPN
1 stop7h 06mDelta
Deal found 3/27$454
Tue 4/309:40 amHPN - MDW
1 stop4h 05mDelta
Fri 5/39:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$455
Sun 4/215:50 amHPN - MDW
1 stop4h 00mDelta
Thu 4/256:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 3/28$456

Cheap Westchester County to Midway flights in March & April 2024

Find cheap flight options from Westchester County to Midway specifically for the months of March and April 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,228,805 searches. Prices were last updated on March 29, 2024.
Tue 4/309:40 amHPN - MDW
1 stop4h 05mDelta
Fri 5/39:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$455
Sun 4/215:50 amHPN - MDW
1 stop4h 00mDelta
Thu 4/256:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 3/28$456
Tue 4/94:29 pmHPN - MDW
1 stop6h 45mDelta
Wed 4/109:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$460
Sat 4/65:55 amHPN - MDW
1 stop3h 51mDelta
Sun 4/75:48 pmMDW - HPN
1 stop4h 26mDelta
Deal found 3/28$474
Fri 4/125:50 amHPN - MDW
1 stop4h 00mDelta
Fri 4/125:45 pmMDW - HPN
1 stop4h 14mDelta
Deal found 3/28$488
Fri 3/295:55 amHPN - MDW
1 stop3h 51mDelta
Sun 3/319:26 amMDW - HPN
1 stop6h 16mDelta
Deal found 3/28$504
Mon 4/226:10 amHPN - MDW
1 stop6h 45mDelta
Thu 4/259:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$516
Mon 4/85:55 amHPN - MDW
1 stop3h 51mDelta
Mon 4/812:50 pmMDW - HPN
1 stop7h 38mDelta
Deal found 3/28$530
Fri 4/2612:45 pmHPN - MDW
1 stop4h 39mDelta
Sun 4/285:45 pmMDW - HPN
1 stop4h 14mDelta
Deal found 3/28$702

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 3,228,805 searches. Data last updated March 29, 2024.
Wed 5/16:10 amHPN - MDW
1 stop17h 04mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/27$344
Wed 5/16:10 amHPN - MDW
1 stop17h 04mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/28$365
Wed 5/15:50 amHPN - MDW
2 stops17h 24mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/27$370
Sat 5/181:29 pmHPN - MDW
1 stop21h 46mMultiple Airlines
Mon 5/207:31 pmMDW - HPN
2 stops40h 15mMultiple Airlines
Deal found 3/28$385
Wed 5/15:50 amHPN - MDW
2 stops17h 24mDelta
Sat 5/46:00 amMDW - HPN
1 stop14h 29mDelta
Deal found 3/28$391
Wed 5/15:50 amHPN - MDW
2 stops11h 20mDelta
Sat 5/49:30 amMDW - HPN
2 stops10h 59mDelta
Deal found 3/27$425
Wed 5/15:50 amHPN - MDW
2 stops12h 30mDelta
Sat 5/49:30 amMDW - HPN
2 stops10h 59mDelta
Deal found 3/28$440
Tue 5/1412:45 pmHPN - MDW
1 stop5h 21mDelta
Sat 5/186:00 amMDW - HPN
1 stop7h 06mDelta
Deal found 3/27$454
Tue 4/309:40 amHPN - MDW
1 stop4h 05mDelta
Fri 5/39:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$455

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 3,228,805 searches. Data last updated March 29, 2024.
Tue 4/94:29 pmHPN - MDW
1 stop6h 45mDelta
Wed 4/109:30 amMDW - HPN
1 stop6h 19mDelta
Deal found 3/28$460
Sat 4/65:55 amHPN - MDW
1 stop3h 51mDelta
Sun 4/75:48 pmMDW - HPN
1 stop4h 26mDelta
Deal found 3/28$474
Fri 4/125:50 amHPN - MDW
1 stop4h 00mDelta
Fri 4/125:45 pmMDW - HPN
1 stop4h 14mDelta
Deal found 3/28$488
Sat 3/3012:45 pmHPN - MDW
1 stop4h 31mDelta
Mon 4/15:48 pmMDW - HPN
1 stop4h 26mDelta
Deal found 3/27$504
Mon 4/85:55 amHPN - MDW
1 stop3h 51mDelta
Mon 4/812:50 pmMDW - HPN
1 stop7h 38mDelta
Deal found 3/28$530
Mon 4/85:55 amHPN - MDW
1 stop3h 51mDelta
Thu 4/116:30 amMDW - HPN
2 stops9h 19mDelta
Deal found 3/28$811
Fri 4/59:40 amHPN - MDW
2 stops8h 28mDelta
Sun 4/75:48 pmMDW - HPN
1 stop4h 26mDelta
Deal found 3/29$932
Fri 4/125:29 pmHPN - MDW
3 stops18h 08mMultiple Airlines
Sun 4/149:23 pmMDW - HPN
3 stops18h 17mMultiple Airlines
Deal found 3/28$1,095
Fri 4/125:50 amHPN - MDW
1 stop4h 00mDelta
Mon 4/1511:20 amMDW - HPN
2 stops10h 39mDelta
Deal found 3/28$1,311

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 3,228,805 searches. Data last updated March 29, 2024.
Fri 5/171:10 pmHPN - MDW
1 stop9h 38mMultiple Airlines
Deal found 3/27$121
Sun 4/77:49 pmHPN - MDW
2 stops29h 48mMultiple Airlines
Deal found 3/28$225
Tue 5/2112:45 pmHPN - MDW
1 stop5h 21mDelta
Deal found 3/28$228
Sun 4/77:49 pmHPN - MDW
3 stops43h 26mMultiple Airlines
Deal found 3/28$245
Fri 4/55:55 amHPN - MDW
1 stop3h 51mDelta
Deal found 3/29$265
Thu 4/47:49 pmHPN - MDW
2 stops29h 48mMultiple Airlines
Deal found 3/27$331
Tue 5/219:05 amHPN - MDW
3 stops13h 26mMultiple Airlines
Deal found 3/28$333
Thu 7/184:29 pmHPN - MDW
1 stop6h 12mDelta
Deal found 3/28$339
Wed 4/35:20 pmHPN - MDW
3 stops24h 41mMultiple Airlines
Deal found 3/27$365

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 3,228,805 searches. Data last updated March 29, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$344 - $1,175

Route

Depart

Return

Price

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

1 stop17h 04m

Chicago Midway

Sat 5/4

1 stop14h 29m

$344

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

1 stop17h 04m

Chicago Midway

Sat 5/4

1 stop14h 29m

$365

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

2 stops17h 24m

Chicago Midway

Sat 5/4

1 stop14h 29m

$370

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/18

1 stop21h 46m

Chicago Midway

Mon 5/20

2 stops40h 15m

$385

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

2 stops17h 24m

Chicago Midway

Sat 5/4

1 stop14h 29m

$391

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

2 stops11h 20m

Chicago Midway

Sat 5/4

2 stops10h 59m

$425

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 5/1

2 stops12h 30m

Chicago Midway

Sat 5/4

2 stops10h 59m

$440

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 5/14

1 stop5h 21m

Chicago Midway

Sat 5/18

1 stop7h 06m

$454

White Plains Westchester CountyChicago Midway

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 4/16

3 stops18h 08m

Chicago Midway

Wed 4/17

3 stops17h 46m

$1,175

Flights are sorted by cheapest first

Deals found on 3/27

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 March 29, 2024.
8.1
Very good
11,402 reviews

Crew

8.6

Food

7.5

Boarding

8.2

Comfort

7.9

Overall

8.1

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.

8.1
Very good
11,402 reviews
8.1
Very good
11,402 reviews

Crew

8.6

Food

7.5

Boarding

8.2

Comfort

7.9

Overall

8.1

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.

7.5
Good
3,036 reviews
8.1
Very good
11,402 reviews

Crew

8.6

Food

7.5

Boarding

8.2

Comfort

7.9

Overall

8.1

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 $344, but on average you can expect to pay $457.

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

    There are currently 12+ 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 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 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 see available direct flights.

  • 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 do 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.

  • 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 3/28.

See more FAQs

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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 3,228,805 searches. Data last updated March 29, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$197Average$379FlexibilityNo cancel feeOn-timeN/A
Search Delta flights

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.

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.

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 can I compare prices from different travel booking sites for flights from Westchester County to Midway?

Cheapflights aggregates prices from various travel booking sites. This allows you to compare prices and choose the best deal.

Can I find deals for flights from Westchester County to Midway that offer flexible cancellation policies?

Cancellation policies vary by airline and fare type. After entering your flight details, you can view the cancellation policies for each deal in the search results. Some deals may offer flexibility in terms of cancellation and changes.

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