HPN to MDW (White Plains to Chicago) Flights

Last Minute Flights from HPN to MDW

Best airfare and ticket deals for HPN to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

Cheapest HPN to MDW Flights

Best airfare and ticket deals for HPN to MDW flights are based on recent deals found by Expedia.com customers within the past 7 days.

OriginDestinationTravel DatesFlights From*
HPNChicagoJune 11 to June 25$262
HPNChicagoAugust 12 to August 20$293
HPNChicagoAugust 13 to August 20$302
HPNChicagoAugust 12 to August 19$303
*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

Which airlines with flights from White Plains, NY Airport (HPN-Westchester County) to MDW allow free cancellation due to COVID-19?
Quite a few airlines now offer flexible airfares so you can book your journey to Chicago Airport with confidence. To locate which carriers have these kinds of tickets, use our filter tool. Simply click the “No change fee” box directly under the “Flexible change policies” heading. Also read through the ticket’s terms and conditions so you know what COVID-19 related changes are permitted.
What airlines fly direct from White Plains Airport to Chicago, IL Airport (MDW-Midway Intl.)?
No airlines fly straight from HPN to Chicago, IL Airport (MDW-Midway Intl.). If you want to visit Chicago, find a flight with at least one stop.
How many flights are there from HPN to MDW?
There are around 5 flights each day from White Plains, NY Airport (HPN-Westchester County) to Chicago, IL Airport (MDW-Midway Intl.), so you have ample opportunities to get to Chicago. Just select a date and time that fits with your plans and lock in your airfare.
How long does it take to fly from White Plains, NY Airport (HPN-Westchester County) to Chicago, IL Airport (MDW-Midway Intl.)?
Around 3 hours and 31 minutes. On a daytime flight? Lock in a seat next to the window and take in the views below. Or, if you’re traveling from White Plains, NY Airport (HPN-Westchester County) to Chicago, IL Airport (MDW-Midway Intl.) during the night, have a snooze and arrive in Chicago refreshed and rejuvenated.
What is the flight distance from White Plains, NY Airport (HPN-Westchester County) to Chicago, IL Airport (MDW-Midway Intl.)?
The short-haul trip from White Plains to Chicago is a quick 730 miles (1150 km). Don’t get too comfortable though — you’ll be landing at Chicago, IL Airport (MDW-Midway Intl.) not long after buckling up.
How many morning flights are there from HPN to MDW?
There are about 14 morning flights from HPN to MDW per week. Delta (DL) operates 14 weekly flights that take off before midday. If you’d like to get going early, book DL’s first flight at 6:29AM.
How many afternoon flights are there from HPN to MDW?
Forget about the early morning check in and select one of the 25 weekly afternoon and evening flights from HPN to MDW. Afternoon and evening services operated by Delta (DL) fly out from 12:50PM. Overall, this carrier has 25 weekly flights departing after midday.
What is the earliest departure time out of White Plains to Chicago?
Depart HPN at 6:29AM and arrive at MDW at 12:40AM. This is the earliest service you’ll find on this route.
What is the latest departure time out of White Plains to Chicago?
The latest flight takes off from HPN at 7:22PM and lands at 12:40AM at MDW. You’ll have lots of time to get ready for this trip.
What is the average price from White Plains to Chicago?
Round-trip flights from HPN to MDW start from $262. Book soon and land 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 perhaps simply to treat yourself to a mini vacation. Regardless of the reasons behind packing your bags and needing to find the cheapest flights from HPN to MDW, we’ve got you covered here at Flights.com.

We present you with some of the hottest 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.