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Book Flights from Chicago to Westchester will help you to find the best deals on flights from Chicago to Westchester. With our search technology, effortlessly searching flight routes across hundreds of airlines has never been easier or more convenient. With, we aim to make it simple and quick to search, select and save on the flights that best suit your needs and budget.

No matter if you are traveling for business or pleasure, we offer a wide range of deals from business class discounts to last minute flight deals to destinations like Westchester. Whether you are planning ahead or looking for last minute tickets, CheapOair has the right flights at the right price. After booking your ticket, explore this page to view blog posts about this destination, learn more about hotels near HPN and read reviews from others who booked their flights with

Frequently Asked Questions - Chicago to Westchester Flights

  • When does the first flight of the day depart from CHI?

    7:45AM United Airlines Flight #3826

  • When does the last flight depart to HPN?

    6:45PM American Airlines Flight #5180

  • What is the travel distance between Chicago and Westchester?

    13 miles

  • How many weekly flights are there between CHI to HPN?

    There are 15 weekly flights between CHI and HPN.

  • How many daily flights fly between Chicago and Westchester?

    There are 2 daily flights between CHI and HPN

  • Which is the busiest day in terms of passengers traffic between CHI to HPN?


  • Which is the nearest airport to Westchester, New York?

    Midway International Airport

  • Which is the nearest airport to Chicago, Illinois?

    Midway International Airport