$287 Cheap Flights from White Plains (HPN) to Chicago (MDW)

View $287 flight on Sat, Sep 6, 2025Opens in a new window

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

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

Prices were available within the past 7 days and start at $287 for one-way flights and $257 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 18 - Sat, Dec 6
HPN
White Plains
MDW
Chicago
$257 Roundtrip, found 3 hours ago
$257
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 18 from White Plains to Chicago, returning Sat, Dec 6, priced at $257 found 3 hours ago
Delta
Sat, Sep 27 - Mon, Sep 29
HPN
White Plains
MDW
Chicago
$287 Roundtrip, found 13 hours ago
$287
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Sep 27 from White Plains to Chicago, returning Mon, Sep 29, priced at $287 found 13 hours ago
Delta
Wed, Nov 19 - Sat, Dec 6
HPN
White Plains
MDW
Chicago
$297 Roundtrip, found 3 hours ago
$297
Roundtrip
found 3 hours ago
Select Delta flight, departing Wed, Nov 19 from White Plains to Chicago, returning Sat, Dec 6, priced at $297 found 3 hours ago
Delta
Mon, Nov 17 - Sat, Dec 6
HPN
White Plains
MDW
Chicago
$302 Roundtrip, found 3 hours ago
$302
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Nov 17 from White Plains to Chicago, returning Sat, Dec 6, priced at $302 found 3 hours ago
Delta
Tue, Nov 18 - Wed, Dec 10
HPN
White Plains
MDW
Chicago
$313 Roundtrip, found 3 hours ago
$313
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 18 from White Plains to Chicago, returning Wed, Dec 10, priced at $313 found 3 hours ago
Delta
Sat, Sep 27 - Fri, Oct 3
HPN
White Plains
MDW
Chicago
$317 Roundtrip, found 13 hours ago
$317
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Sep 27 from White Plains to Chicago, returning Fri, Oct 3, priced at $317 found 13 hours ago
Delta
Tue, Nov 18 - Fri, Dec 5
HPN
White Plains
MDW
Chicago
$320 Roundtrip, found 3 hours ago
$320
Roundtrip
found 3 hours ago
Select Delta flight, departing Tue, Nov 18 from White Plains to Chicago, returning Fri, Dec 5, priced at $320 found 3 hours ago
Delta
Sat, Sep 27 - Wed, Oct 8
HPN
White Plains
MDW
Chicago
$323 Roundtrip, found 6 days ago
$323
Roundtrip
found 6 days ago
Select Delta flight, departing Sat, Sep 27 from White Plains to Chicago, returning Wed, Oct 8, priced at $323 found 6 days ago
Delta
Wed, Sep 24 - Thu, Oct 2
HPN
White Plains
MDW
Chicago
$327 Roundtrip, found 13 hours ago
$327
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, Sep 24 from White Plains to Chicago, returning Thu, Oct 2, priced at $327 found 13 hours ago
Delta
Sat, Sep 27 - Wed, Oct 1
HPN
White Plains
MDW
Chicago
$332 Roundtrip, found 13 hours ago
$332
Roundtrip
found 13 hours ago
Select Delta flight, departing Sat, Sep 27 from White Plains to Chicago, returning Wed, Oct 1, priced at $332 found 13 hours ago

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $493
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $493
Flights from White Plains (HPN) to Chicago (MDW)
Origin airport
Westchester County
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$257
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 November. 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 $287 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?
Lock in a cheap one-way flight from $287 or cheap return flight from $257 from Westchester County Airport (HPN) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight offers on this route.
What is the cheapest month to fly from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Flying in November is a good way to save, as it's the cheapest month for flights between HPN and MDW. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Select your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest HPN to MDW flight.
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.