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Flights from White Plains to Chicago
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Find White Plains to Chicago flights starting at €106.

We've found these cheap flights for you. You can book one-way or return flight tickets.

  • One way
  • Round-trip
      • Cheapest nonstop
        HPN07:15
        2h 33m
        Nonstop
        ORD08:48
        Fri, Dec 13|White Plains - Chicago|American Airlines
        €106€230
        54% OFF
        54% OFF
        €230€106

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Fri, Dec 13, arriving at O'Hare International Airport. One-way Prices start from €106 including taxes and charges.

      • HPN07:15
        2h 34m
        Nonstop
        ORD08:49
        Wed, Jan 1|White Plains - Chicago|American Airlines
        €131€230
        43% OFF
        43% OFF
        €230€131

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Wed, Jan 1, arriving at O'Hare International Airport. One-way Prices start from €131 including taxes and charges.

      • HPN16:30
        2h 30m
        Nonstop
        ORD18:00
        Tue, Dec 31|White Plains - Chicago|American Airlines
        €151€230
        35% OFF
        35% OFF
        €230€151

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Tue, Dec 31, arriving at O'Hare International Airport. One-way Prices start from €151 including taxes and charges.

      • HPN16:30
        2h 42m
        Nonstop
        ORD18:12
        Wed, Jan 8|White Plains - Chicago|American Airlines
        €160
        €160

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Wed, Jan 8, arriving at O'Hare International Airport. One-way Prices start from €160 including taxes and charges.

      • HPN12:00
        2h 29m
        Nonstop
        ORD13:29
        Sat, Dec 14|White Plains - Chicago|American Airlines
        €163
        €163

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Sat, Dec 14, arriving at O'Hare International Airport. One-way Prices start from €163 including taxes and charges.

      • HPN07:15
        2h 33m
        Nonstop
        ORD08:48
        Sun, Dec 15|White Plains - Chicago|American Airlines
        €189
        €189

        Choose American Airlines flights from White Plains to Chicago. The one-way direct flight with American Airlines departs from Westchester County Airport on Sun, Dec 15, arriving at O'Hare International Airport. One-way Prices start from €189 including taxes and charges.

      • HPN12:30
        9h 7m
        1 stop
        ORD20:37
        Wed, Dec 18|White Plains - Chicago|Delta Air Lines
        €147
        €147

        Choose Delta Air Lines flights from White Plains to Chicago. The one-way connecting flight with Delta Air Lines departs from Westchester County Airport on Wed, Dec 18, arriving at O'Hare International Airport. One-way Prices start from €147 including taxes and charges.

      • HPN12:49
        7h 3m
        1 stop
        ORD18:52
        Thu, Nov 28|White Plains - Chicago|Delta Air Lines
        €147
        €147

        Choose Delta Air Lines flights from White Plains to Chicago. The one-way connecting flight with Delta Air Lines departs from Westchester County Airport on Thu, Nov 28, arriving at O'Hare International Airport. One-way Prices start from €147 including taxes and charges.

      • HPN17:24
        16h 30m
        1 stop
        MDW08:54
        Wed, Jan 8|White Plains - Chicago|Delta Air Lines
        €162
        €162

        Choose Delta Air Lines flights from White Plains to Chicago. The one-way connecting flight with Delta Air Lines departs from Westchester County Airport on Wed, Jan 8, arriving at Midway International Airport. One-way Prices start from €162 including taxes and charges.

      • HPN07:30
        9h 32m
        1 stop
        ORD16:02
        Wed, Dec 11|White Plains - Chicago|Jetblue Airways
        €163
        €163

        Choose Jetblue Airways flights from White Plains to Chicago. The one-way connecting flight with Jetblue Airways departs from Westchester County Airport on Wed, Dec 11, arriving at O'Hare International Airport. One-way Prices start from €163 including taxes and charges.

      • HPN13:00
        3h 5m
        Nonstop
        CHI14:00
        Tue, Dec 3|White Plains - Chicago|American Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from White Plains to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Find Cheapest Airlines Flying from White Plains to Chicago

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.

American Airlines
From €106
Delta Air Lines
From €147
Jetblue Airways
From €163
Cape Air
From €362

Find more flights and airlines

Alternative Routes for White Plains to Chicago Flights

Searching for potential routes that might be cheaper and faster? Check out these alternative flights from White Plains to Chicago.

  • Cheapest
    American Airlines
    HPN
    07:15
    2h 33m
    Nonstop
    ORD
    08:48
    Westchester County Airport - O'Hare International Airport
    Fri, Dec 13American Airlines
    €106
  • Delta Air Lines
    HPN
    17:24
    16h 30m
    1 transfer
    MDW
    08:54
    Westchester County Airport - Midway International Airport
    Wed, Jan 8Delta Air Lines
    €162
  • Delta Air Lines
    HPN
    17:24
    16h 30m
    1 transfer
    MDW
    08:54
    Westchester County Airport - Midway International Airport
    Wed, Jan 8Delta Air Lines
    €162
    Find More Flights

FAQ

  • When are flight tickets from White Plains (HPN) to Chicago (CHI) the cheapest?

    Airlines adjust prices for flights from White Plains to Chicago based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the cheapest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much are flights from White Plains (HPN) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around €350.

  • How long is the flight from White Plains (HPN) to Chicago (CHI)?

    It takes about 2 hours 36 minutes to fly from White Plains (HPN) to Chicago (CHI).

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25km, by taxi about 40 minutes.
    • The distance from Midway International Airport to downtown is about 14km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from White Plains (HPN) to Chicago (CHI)?

    Airlines with flights from White Plains (HPN) to Chicago (CHI): Alaska Airlines, Qatar Airways and American Airlines.

  • What's the most popular airline for direct flights from White Plains (HPN) to Chicago (CHI)?

    United Airlines operates 2 direct flights from White Plains (HPN) to Chicago (CHI).

  • How many airports in Chicago (CHI)?

How to find a cheap flight from White Plains to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from White Plains to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information for White Plains to Chicago Flights

Cheapest direct flight price€105
Cheapest return ticket price€287
Off-season travel monthOctober
Peak season for travelJanuary
Flight distance1,162.96km
Average flight time2 hours 36 minutes
Popular airlineAmerican Airlines

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