$269 Cheap Flights from White Plains (HPN) to Chicago (MDW)

View $269 flight on Fri, Aug 29, 2025Opens in a new window

Popular airlines from Westchester County Airport (HPN) to Chicago Midway Airport (MDW)

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Cheap Flights from White Plains to Chicago (HPN-MDW)

Prices were available within the past 7 days and start at $269 for one-way flights and $297 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Mon, Aug 25 - Wed, Sep 10
HPN
White Plains
MDW
Chicago
$297 Roundtrip, found 2 days ago
$297
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 25 from White Plains to Chicago, returning Wed, Sep 10, priced at $297 found 2 days ago
Delta
Mon, Aug 25 - Mon, Sep 8
HPN
White Plains
MDW
Chicago
$300 Roundtrip, found 2 days ago
$300
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 25 from White Plains to Chicago, returning Mon, Sep 8, priced at $300 found 2 days ago
Delta
Wed, Sep 3 - Mon, Sep 15
HPN
White Plains
MDW
Chicago
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Sep 3 from White Plains to Chicago, returning Mon, Sep 15, priced at $303 found 2 days ago
Delta
Fri, Sep 5 - Tue, Sep 23
HPN
White Plains
MDW
Chicago
$312 Roundtrip, found 2 days ago
$312
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Sep 5 from White Plains to Chicago, returning Tue, Sep 23, priced at $312 found 2 days ago
Delta
Tue, Aug 12 - Thu, Sep 4
HPN
White Plains
MDW
Chicago
$315 Roundtrip, found 3 days ago
$315
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Aug 12 from White Plains to Chicago, returning Thu, Sep 4, priced at $315 found 3 days ago
Delta
Tue, Sep 23 - Sat, Oct 4
HPN
White Plains
MDW
Chicago
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep 23 from White Plains to Chicago, returning Sat, Oct 4, priced at $317 found 2 days ago
Delta
Wed, Aug 27 - Mon, Sep 8
HPN
White Plains
MDW
Chicago
$320 Roundtrip, found 2 days ago
$320
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 27 from White Plains to Chicago, returning Mon, Sep 8, priced at $320 found 2 days ago
Delta
Mon, Aug 25 - Sat, Aug 30
HPN
White Plains
MDW
Chicago
$322 Roundtrip, found 2 days ago
$322
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Aug 25 from White Plains to Chicago, returning Sat, Aug 30, priced at $322 found 2 days ago
Delta
Fri, Aug 29 - Mon, Sep 15
HPN
White Plains
MDW
Chicago
$325 Roundtrip, found 3 days ago
$325
Roundtrip
found 3 days ago
Select Delta flight, departing Fri, Aug 29 from White Plains to Chicago, returning Mon, Sep 15, priced at $325 found 3 days ago
Delta
Wed, Aug 20 - Wed, Sep 3
HPN
White Plains
MDW
Chicago
$327 Roundtrip, found 2 days ago
$327
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 20 from White Plains to Chicago, returning Wed, Sep 3, priced at $327 found 2 days ago
Flights from White Plains (HPN) to Chicago (MDW)
Origin airport
Westchester County
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$297
Distance
728 mi

White Plains to Chicago Flights

The cheapest times to fly from White Plains to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from White Plains to Chicago are during the month of August. You can find some of the cheapest flights from White Plains to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from White Plains to Chicago

Sunday is one of the best days to book for cheap flights from White Plains to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from White Plains to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from White Plains to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $269 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap White Plains to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your White Plains to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) cost?
Discover the latest flight deals from HPN to MDW by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from HPN to MDW?
The cheapest flights from HPN to MDW are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from HPN to MDW?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that'll take you from HPN to MDW. Sort your results by "Price (lowest to highest)" to snap up a great deal.
How many flights per day from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Direct flights from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with our filter tool. Enter your travel details and choose either "1 Stop" or "2+ Stops."
What day of the week has the most flights from HPN to MDW?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during peak travel times or public holidays.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Select a flight from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) that takes off before 3 PM to reduce the likelihood of delays. Later departures are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
What airports do you fly into for Chicago from Westchester County Airport (HPN)?
If you're traveling on a direct flight from Westchester County Airport (HPN) to Chicago, O'Hare Intl. Airport (ORD) is the only airport you can touch down at.
Is it cheaper to buy a plane ticket from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) last-minute?
Booking your flight from HPN to MDW shortly before your getaway is typically more expensive. However, if you're flexible with your departure dates and times, you could snag a cheap last-minute fare.
Is it cheaper to book a HPN to MDW flight and hotel package?
You'll generally save money by booking a HPN to MDW flight and hotel package compared to booking separately. In fact, you could save hundreds of dollars by bundling with Expedia. And it's easy to manage it all in one place. After choosing your ideal accommodations and flights, consider other add-ons like car rentals, tours and activities.
Can I cancel or change the date of my flight from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
If you booked your HPN to MDW flight within the last 24 hours, you may be able to cancel or modify it at no cost. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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*Available to One Key members.