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

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

  • Plan, book, fly with confidence

  • trending down icon
    Be in the know
    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon
    Book smarter
    Save up to 55% on select hotels after you book a flight*
  • payments icon
    Earn twice
    Earn your airline miles on top of our rewards
    Sign in
Flight from White Plains to Chicago route information
Origin airport
Westchester County
Destination airport
Midway Intl.
Distance
1164 km

Perfect flights from White Plains to Chicago

Embark on an unforgettable journey without breaking the bank with Expedia's incredible deals on cheap flights from White Plains to Chicago. Whether you're aching for a romantic escape with your partner, craving an adventurous solo expedition, or yearning to immerse yourself in the local history and culture, we've got you covered.
 
Picture yourself strolling through the streets of , surrounded by breathtaking architecture and absorbing the vibrant atmosphere of this captivating city. Indulge in the mouth-watering local specialties, from tantalizing street food to exquisite fine dining. With Expedia, you can experience all of this and more, without sacrificing your budget.
 
Our flexible Westchester County to Midway Intl. ticket options cater to your travel preferences, with incredible one-way fares and roundtrip prices . Whether you're planning a short city break or a longer adventure, our dynamic pricing ensures that you find the best deals for your journey.
 
But the magic doesn't stop there. Expedia offers a range of partner services to enhance your trip. Rent a car at Midway Intl. and explore and its surrounding areas at your own pace. Discover hidden gems off the beaten path, and create unforgettable memories. We also provide a handpicked selection of accommodations, from charming bed and breakfasts to luxury hotels, ensuring that you have a comfortable and memorable stay.
 
Planning your next great adventure is a breeze with Expedia. Our user-friendly platform, unbeatable prices, and round-the-clock customer support are designed to make your travel experience seamless and stress-free. So, why wait? Book your to travel arrangements today and embark on the journey of a lifetime in Chicago.

Frequently asked questions

How much is a flight from White Plains Airport to Midway Airport?
Based on fares advertised within the last 7 days on Expedia for flights departing within the next year, round-trip journeys between Westchester County Airport (HPN) and Midway Intl. Airport (MDW) start from . Make your booking ASAP to score the best price for your adventure. Prices and availability are subject to change. Additional terms apply.
Do I need to pay a cancellation fee if I cancel my flight from HPN to Midway Intl. Airport (MDW)?
When it comes to cancellation fees, each airline has a different set of terms and conditions. If you decide to cancel your holiday, head to our Customer Service Portal.
How do I find cheap flights from Westchester County Airport (HPN) to MDW that have flexible change policies?
Many airlines offer the option to reschedule your flight without a change fee. All you pay is the difference between the original flight and the new flight. When you’re searching for HPN to MDW flights, you’ll see a “no change fees” filter for you to select.
How far is the flight from HPN to MDW?
That new movie you’ve been desperate to see will just have to wait — the flight distance between Westchester County Airport (HPN) and Midway Airport is only 1,150 kilometres. The captain will be telling you to put your seat upright for touchdown before you know it.
Which airlines fly direct from White Plains Airport to MDW?
Flying nonstop between HPN and MDW isn’t possible at present. However, you’ll still be able to book a flight to Chicago with at least one stop.
Are HPN to Chicago Airport flight tickets cheaper when they're purchased at the last minute?
Booking your trip from HPN to Midway Airport last minute could save you some serious cash. However, it could end up costing a great deal more! If you’d rather play it safe, book well ahead of your departure date. In fact, Expedia has some of the best bargains up to 12 months in advance. If your preferred air carrier hasn’t released tickets yet, check back regularly as deals are updated on Expedia all the time.
*Available to Expedia members.