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$169+ Cheap flights from White Plains (HPN) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in September or November, booked 28 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from White Plains to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated agosto 14, 2025.

Round-trip from

$349
(American Airlines)

One-way from

$200
(American Airlines)

Popular in

June

Cheapest in

September

Average price

$452

Good round-trip deal

$380 or less

Good one-way deal

$198 or less
From White Plains Westchester County to Chicago (CHI)
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One-way flight from White Plains Westchester County to Chicago (CHI)
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Highest demand for flights based on searches. 3% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 0% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Price to beat on a round-trip flight from White Plains Westchester County to Chicago (CHI).
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Price to beat on a one-way flight from White Plains Westchester County to Chicago (CHI).
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Find flight deals from White Plains to Chicago

Cheapest flights from White Plains to Chicago
Explore the most affordable flight options available from White Plains to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on agosto 14, 2025.

This American Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/14:30 pmHPN - ORD
Nonstop2h 35mAmerican Airlines
mié. 10/298:17 amORD - HPN
Nonstop2h 12mAmerican Airlines
Deal found 8/14$349
This KAYAK deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/116:30 amHPN - ORD
2 stops10h 28mAmerican Airlines
lun. 10/138:50 pmORD - HPN
2 stops12h 44mAmerican Airlines
Deal found 8/13$350
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/185:20 pmHPN - ORD
1 stop15h 45mDelta
mar. 9/237:10 amORD - HPN
1 stop7h 39mDelta
Deal found 8/13$367
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/136:00 amHPN - MDW
1 stop4h 47mDelta
mar. 9/166:00 amMDW - HPN
1 stop7h 29mDelta
Deal found 8/14$369
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/112:42 pmHPN - ORD
1 stop4h 38mDelta
mié. 10/297:10 amORD - HPN
1 stop3h 49mDelta
Deal found 8/14$369
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/254:30 pmHPN - ORD
Nonstop2h 41mAmerican Airlines
lun. 10/276:29 pmORD - HPN
Nonstop2h 30mAmerican Airlines
Deal found 8/13$380
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/113:25 pmHPN - ORD
1 stop26h 39mDelta
sáb. 9/133:58 pmORD - HPN
1 stop23h 37mDelta
Deal found 8/12$382
This American Airlines deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/912:00 pmHPN - ORD
Nonstop2h 36mAmerican Airlines
sáb. 9/138:15 amORD - HPN
Nonstop2h 14mAmerican Airlines
Deal found 8/11$384
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/2012:42 pmHPN - ORD
1 stop9h 52mDelta
lun. 9/229:10 amORD - HPN
2 stops12h 08mDelta
Deal found 8/13$387
This KAYAK deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/96:30 amHPN - ORD
2 stops12h 40mAmerican Airlines
mié. 9/108:54 pmORD - HPN
2 stops12h 36mAmerican Airlines
Deal found 8/13$388
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/206:30 amHPN - ORD
2 stops13h 06mAmerican Airlines
mar. 9/2312:24 pmORD - HPN
2 stops10h 02mAmerican Airlines
Deal found 8/13$389
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/2512:55 pmHPN - MDW
1 stop6h 30mDelta
lun. 10/276:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 8/14$400

Cheapflights Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

Fly from

White Plains

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mié. 9/24

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

mié. 10/1

7:37 pm-10:59 pm

Nonstop2h 22m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 9/27

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

mié. 10/1

8:15 am-11:29 am

Nonstop2h 14m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mié. 9/17

6:00 am-7:30 am

Nonstop2h 30m

Chicago O'Hare Intl

sáb. 9/20

7:37 pm-10:59 pm

Nonstop2h 22m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 8/30

6:00 am-7:36 am

Nonstop2h 36m

Chicago O'Hare Intl

dom. 8/31

8:17 am-11:28 am

Nonstop2h 11m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 9/13

12:00 pm-1:36 pm

Nonstop2h 36m

Chicago O'Hare Intl

mar. 9/16

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mié. 10/1

12:00 pm-1:36 pm

Nonstop2h 36m

Chicago O'Hare Intl

mié. 10/29

8:17 am-11:29 am

Nonstop2h 12m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mar. 9/16

4:30 pm-6:05 pm

Nonstop2h 35m

Chicago O'Hare Intl

mié. 9/24

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 10/11

6:30 am-3:58 pm

2 stops10h 28m

Chicago O'Hare Intl

lun. 10/13

8:50 pm-10:34 am

2 stops12h 44m

$350

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

sáb. 9/13

6:00 am-9:47 am

1 stop4h 47m

Chicago Midway

mar. 9/16

6:00 am-2:29 pm

1 stop7h 29m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

sáb. 9/27

4:29 pm-9:10 pm

1 stop5h 41m

Chicago Midway

mié. 10/1

6:00 am-11:59 am

1 stop4h 59m

$369

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Showing 1-10 of 37 results
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Best time to book a flight from White Plains to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from White Plains with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from White Plains to Chicago

How far ahead should I book a flight from White Plains to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from White Plains to Chicago. Price data was last updated on August 8, 2025.

The best time to book flights from White Plains to Chicago is 28 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from White Plains to Chicago?

Currently, August is the cheapest month in which you can book a flight from White Plains to Chicago (average of $245). Flying from White Plains to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HPN to CHI?

Find hourly flight availability from White Plains to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated agosto 14, 2025.

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 68% on the cost of your flight, compared to a flight in the morning.

Weekly flight availability from White Plains to Chicago

Explore weekly flight availability from White Plains to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated agosto 14, 2025.

The most flights from HPN to CHI are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated agosto 14, 2025.
Peruse reviews from past customers who have flown with Delta and American Airlines from White Plains to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,980 reviews

Boarding

8.2

Entertainment

7.9

Comfort

7.9

Overall

8.0

Crew

8.5

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

Related info for your journey

Find useful and relevant information for your journey from White Plains to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from White Plains to Chicago?

    Most people fly from White Plains Westchester County (HPN) if they book a flight from White Plains to Chicago. On average, Westchester County has 8 outbound flights to Chicago per day from 2 airlines. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.

  • What are the cheapest airlines flying from White Plains to Chicago round-trip?

    Flying on United Airlines is currently your cheapest option to Chicago, with prices starting at $96. Another option worth looking into is American Airlines, starting at $334 round trip. Users have found that United Airlines is 79% cheaper than the other options available to this destination.

  • What are the most reliable airlines from White Plains to Chicago?

    Before booking your flight to Chicago from White Plains, check out the most reliable airlines to get you to your destination on time: Alaska Airlines (76%), American Airlines (75%), Envoy Air( 75%).

  • What are the cheapest flights from White Plains to Chicago?

    The cheapest flight price from White Plains to Chicago is $148. On average you can expect to pay $587. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $283.

  • Can I find deals for flights from White Plains to Chicago that include hotel bookings?

    Yes. In addition to deals on White Plains to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from White Plains to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from White Plains to Chicago.

  • Can I find deals for business class flights from White Plains to Chicago?

    Yes. Cheapflights offers flight deals from White Plains to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from White Plains to Chicago?

    Currently, August is the cheapest month in which you can book a flight from White Plains to Chicago (average of $245). Flying from White Plains to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for White Plains to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from White Plains to Chicago

Discover the top 2 airlines that operate flights from White Plains to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$96Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$334Average$459FlexibilityNo cancel feeOn-time71%

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