$159 Cheap flights from Westchester County to Midway Intl. (HPN to MDW)

Discover our best flights from White Plains HPN to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 

Find our best return flights from White Plains HPN to Chicago MDW at the right price  

Airfares to Chicago MDW from White Plains HPN currently cost between $283 and $414. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 

Book one-way flights from White Plains HPN to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from White Plains HPN to Chicago MDW on Travelocity starting at $159. Prices and availability subject to change. Additional terms may apply. 

Get to Chicago MDW from White Plains HPN quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from HPN to take around hour(s) min(s).  

Find our cheapest airfares for flights from White Plains HPN to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from HPN. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  

Get our best airfare deals for your flight from White Plains HPN to Chicago MDW today 

If you’re flexible about when you travel, July is usually the cheapest month to fly from White Plains HPN to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 

Book flexible airline tickets for flights to Chicago MDW from White Plains HPN 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from HPN have this option.  

Travel with confidence when you book flights to Chicago MDW from White Plains HPN with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving.