HPN to MDW (White Plains to Chicago) Flights

Last Minute Flights from HPN to MDW

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
HPNChicagoMay 2 to May 20$300
*Prices include taxes and fees

Cheapest HPN to MDW Flights

Price found within the past 7 days for the specified period. Click for updated prices.

OriginDestinationTravel DatesFlights From*
HPNChicagoJune 17 to June 24$283
HPNChicagoJune 17 to July 3$296
HPNChicagoJune 25 to July 10$298
HPNChicagoJune 18 to June 24$300
*Prices include taxes and fees
HPN to MDW Flight Details
Origin airport
Westchester County
Origin airport IATA code
HPN
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Distance
728 mi

Frequently asked questions

What airlines fly direct from Westchester County Airport (HPN) to Midway Intl. Airport (MDW)?
At the moment there are no air carriers flying nonstop from White Plains Airport to Chicago Airport. Break up the journey with one or two stops to reach Chicago.
How many flights are there from HPN to MDW?
There are no less than 8 flights per day from White Plains, NY (HPN-Westchester County) to Chicago, IL (MDW-Midway Intl.), so you have ample opportunities to get to Chicago. Just select a date that works best for you and lock in your seat.
How long does it take to fly from White Plains, NY (HPN-Westchester County) to Chicago, IL (MDW-Midway Intl.)?
While you won’t be buckled in your seat for a lifetime from White Plains, NY (HPN-Westchester County) to Chicago, IL (MDW-Midway Intl.), 3 hours and 46 minutes isn’t a quick ride either. Look into upgrading your ticket if you’d like the comfort of more leg space.
What is the flight distance from White Plains, NY (HPN-Westchester County) to Chicago, IL (MDW-Midway Intl.)?
The short-haul flight between West Harrison and Chicago is a quick 730 miles (1,150 1). Don’t settle in too much though — you’ll be coming into Chicago, IL (MDW-Midway Intl.) not all that long after taking off.
How many morning flights are there from HPN to MDW?
Each week, 23 morning flights jet out from HPN to MDW, with 23 operated by Delta Air Lines (DL). If you’d prefer to be soaring through the air as early as possible, DL’s first flight departs at 5:50AM.
How many afternoon flights are there from HPN to MDW?
With 34 weekly afternoon and evening flights from HPN to MDW, there’s no need to order that hotel wake-up call. Compare the deals from Delta Air Lines (DL) and you’ll have your choice of 34 flights every week that take off after midday. The first departs at 12:45PM.
What is the earliest departure time out of West Harrison to Chicago?
5:50AM is the earliest flight that leaves from HPN, arriving at MDW at 5:23PM. Save valuable time in the morning by having your suitcase packed and ready to be thrown into your rideshare.
What is the latest departure time out of West Harrison to Chicago?
From HPN, the latest flight departs at 6:45PM and touches down at MDW at 6:59PM. If you’re not a fan of early mornings, this flight has your name on it.
What is the average price from West Harrison to Chicago?
Round-trip tickets from HPN to MDW start from $283. Book your adventure today and score a great deal. This price was available on Flights.com within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

White Plains to Chicago Flights

Whether it’s for an obligation or the sake of your sanity, sometimes you need to get away. Maybe you need flights from White Plains to Chicago to attend your cousin’s wedding, to pitch a business idea to your boss, or simply treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find our cheapest flights from HPN to MDW, we’ve got you covered here at Flights.com.

We present you with some of the most affordable deals on airfare, so stop that Google flights search. We want you to spend less on your flight from White Plains to Chicago, so you can spend more during your getaway. With Flights.com, you’ll find it simple to land airline tickets with itineraries matching your travel schedule. What’s more, we provide you with all the information you need to confidently make reservations on your family, business, or personal trip.