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Cheap Flights from White Plains to Chicago
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Cheap Flights from White Plains to Chicago starting at S$ 118

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

  • One way
  • Round-trip
      • HPN13:10
        9h 28m
        1 stop
        MDW21:38
        Fri, May 3|White Plains - Chicago|Breeze Airways
        S$ 118S$ 339
        65% OFF
        65% OFF
        S$ 339S$ 118
      • HPN12:29
        2h 31m
        Direct
        ORD14:00
        Sun, May 26|White Plains - Chicago|American Airlines
        S$ 180S$ 339
        47% OFF
        47% OFF
        S$ 339S$ 180
      • HPN12:45
        5h 21m
        1 stop
        MDW17:06
        Tue, May 14|White Plains - Chicago|Delta Air Lines
        S$ 184S$ 339
        46% OFF
        46% OFF
        S$ 339S$ 184
      • HPN06:50
        10h 55m
        1 stop
        ORD16:45
        Tue, May 7|White Plains - Chicago|Jetblue Airways
        S$ 184
        S$ 184
      • HPN08:00
        16h 4m
        1 stop
        MDW23:04
        Tue, Apr 30|White Plains - Chicago|Jetblue Airways
        S$ 188
        S$ 188
      • HPN13:55
        10h 48m
        1 stop
        ORD23:43
        Wed, May 8|White Plains - Chicago|Jetblue Airways
        S$ 200
        S$ 200
      • HPN18:55
        4h 12m
        1 stop
        ORD22:07
        Thu, Apr 25|White Plains - Chicago|American Airlines
        S$ 224
        S$ 224
      • HPN15:00
        5h 35m
        1 stop
        ORD19:35
        Wed, May 8|White Plains - Chicago|Delta Air Lines
        S$ 252
        S$ 252
      • HPN15:00
        8h 1m
        1 stop
        MDW22:01
        Sat, May 18|White Plains - Chicago|Delta Air Lines
        S$ 252
        S$ 252
      • HPN13:29
        6h 4m
        1 stop
        ORD18:33
        Wed, May 1|White Plains - Chicago|Breeze Airways
        S$ 258
        S$ 258
      • HPN13:00
        3h 5m
        Direct
        CHI14:00
        Thu, May 2|White Plains - Chicago|Breeze Airways
        Find More Flights
        Find More Flights

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

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 lowest average weekly prices of the corresponding route on Trip.com.
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.

Breeze Airways
From S$ 118
American Airlines
From S$ 180
Delta Air Lines
From S$ 184
Jetblue Airways
From S$ 184
ANA airlines

Find more flights and airlines

Alternative Routes from White Plains to Chicago

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

  • Cheapest
    Breeze Airways
    HPN
    13:10
    9h 28m
    1 transfer
    MDW
    21:38
    Westchester County Airport - Midway International Airport
    Fri, May 3Breeze Airways
    S$ 118
  • American Airlines
    HPN
    12:29
    2h 31m
    Direct
    ORD
    14:00
    Westchester County Airport - O'Hare International Airport
    Sun, May 26American Airlines
    S$ 180
  • American Airlines
    HPN
    12:29
    2h 31m
    Direct
    ORD
    14:00
    Westchester County Airport - O'Hare International Airport
    Sun, May 26American Airlines
    S$ 180
    Find More Flights

Frequently Asked Questions

  • When to buy 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 is a flight from White Plains (HPN) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around S$ 599.

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

    It takes about 2 hours 32 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 time does the earliest flight from White Plains to Chicago depart?

    The earliest flight departs from White Plains (HPN) at 06:20 and arrives in Chicago (ORD) at 08:03.

  • What time does the latest flight from White Plains to Chicago depart?

    The latest flight departs from White Plains (HPN) at 18:04 and arrives in Chicago (ORD) at 19:47.

  • 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): Qatar Airways, American Airlines and Alaska 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?

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

Find cheapest flight ticket from White Plains to Chicago

Cheapest direct flight price

S$ 117

Cheapest return ticket price

S$ 424

Cheapest month

March

Peak season for travel

October

Flight distance

1,162.96km

Average flight time

2 hours 32 minutes

Popular airline

Delta Air Lines

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