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$80+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Dec 19 — Dec 261
Fri 12/19
Fri 12/26
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 March, booked 66 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

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 November 19, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/1812:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Sat 1/38:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 11/18$380
This Delta deal was found by Cheapflights users on 11/18. 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.
Sat 12/1312:45 pmHPN - MDW
1 stop12h 02mDelta
Tue 12/166:00 amMDW - HPN
1 stop15h 09mDelta
Deal found 11/18$383
This Delta deal was found by Cheapflights users on 11/18. 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.
Sat 12/1312:45 pmHPN - ORD
1 stop10h 58mDelta
Tue 12/169:49 amORD - HPN
1 stop11h 20mDelta
Deal found 11/18$383
This Delta deal was found by Cheapflights users on 11/18. 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.
Mon 12/295:16 pmHPN - ORD
1 stop4h 20mDelta
Wed 12/316:02 pmORD - HPN
1 stop16h 57mDelta
Deal found 11/18$392
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Mon 11/244:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Sat 11/298:10 pmORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 11/18$399
This Delta deal was found by Cheapflights users on 11/18. 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.
Thu 12/1810:29 amHPN - ORD
1 stop7h 25mDelta
Thu 1/15:30 amORD - HPN
1 stop5h 30mDelta
Deal found 11/18$400
This Kiwi.com deal was found by Cheapflights users on 11/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/18:00 amHPN - ORD
2 stops26h 01mMultiple Airlines
Thu 12/47:40 amORD - HPN
1 stop26h 48mMultiple Airlines
Deal found 11/18$408
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/184:30 pmHPN - ORD
Nonstop2h 52mAmerican Airlines
Fri 1/28:10 amORD - HPN
Nonstop2h 19mAmerican Airlines
Deal found 11/18$411
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 11/277:10 amHPN - ORD
Nonstop2h 44mAmerican Airlines
Thu 11/2712:48 pmORD - HPN
Nonstop2h 11mAmerican Airlines
Deal found 11/18$414
This Delta deal was found by Cheapflights users on 11/19. 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.
Mon 11/246:41 pmHPN - MDW
1 stop5h 59mDelta
Tue 12/26:00 amMDW - HPN
1 stop5h 00mDelta
Deal found 11/19$419
This Delta deal was found by Cheapflights users on 11/18. 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.
Mon 11/245:14 pmHPN - ORD
1 stop4h 15mDelta
Wed 12/310:45 amORD - HPN
1 stop4h 04mDelta
Deal found 11/18$419
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/181:35 pmHPN - ORD
1 stop6h 47mAmerican Airlines
Thu 1/112:50 pmORD - HPN
Nonstop2h 09mAmerican Airlines
Deal found 11/18$421

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 November 19, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$380
(American Airlines)

One-way from

$80
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$504

Good round-trip deal

$428 or less

Good one-way deal

$205 or less
Provider with most accurate pricing for White Plains Westchester County-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for White Plains Westchester County-Chicago (CHI) flights.
Search Deals
From White Plains Westchester County to Chicago (CHI)
Search Deals
One-way flight from White Plains Westchester County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from White Plains Westchester County to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from White Plains Westchester County to Chicago (CHI).
Search Deals

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 November 19, 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

Thu 12/18

12:00 pm-1:43 pm

Nonstop2h 43m

Chicago O'Hare Intl

Sat 1/3

8:10 am-11:29 am

Nonstop2h 19m

$380

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 12/13

12:45 pm-11:47 pm

1 stop12h 02m

Chicago Midway

Tue 12/16

6:00 am-10:09 pm

1 stop15h 09m

$383

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 2/27

12:33 pm-5:37 pm

1 stop6h 04m

Chicago Midway

Sat 2/28

6:00 am-12:08 pm

1 stop5h 08m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 12/22

6:30 am-10:50 am

1 stop5h 20m

Chicago O'Hare Intl

Sat 1/3

11:35 am-6:22 pm

1 stop5h 47m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 4/22

6:00 am-11:56 am

1 stop6h 56m

Chicago Midway

Sun 4/26

6:00 am-12:14 pm

1 stop5h 14m

$400

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 1/1

12:55 pm-5:26 pm

1 stop5h 31m

Chicago Midway

Sat 1/3

9:29 am-3:49 pm

1 stop5h 20m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 1/1

6:03 am-12:12 pm

1 stop7h 09m

Chicago O'Hare Intl

Sun 1/4

7:00 am-11:59 am

1 stop3h 59m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 12/19

12:55 pm-4:22 pm

1 stop4h 27m

Chicago O'Hare Intl

Wed 1/7

7:05 am-2:26 pm

1 stop6h 21m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 12/19

12:55 pm-4:22 pm

1 stop4h 27m

Chicago O'Hare Intl

Tue 1/6

7:05 am-2:26 pm

1 stop6h 21m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sun 12/28

5:16 pm-8:36 pm

1 stop4h 20m

Chicago O'Hare Intl

Sat 1/3

9:41 am-3:49 pm

1 stop5h 08m

$400

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 39 results
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Compare providers for flights from White Plains to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from White Plains to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on White Plains-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on White Plains-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from White Plains-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on White Plains-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for White Plains-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 November 14, 2025.

The best time to book flights from White Plains to Chicago is 66 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, May is the cheapest month in which you can book a flight from White Plains to Chicago (average of $55). Flying from White Plains to Chicago in July is currently the most expensive (average of $126). 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 November 19, 2025.

It’s optimal to fly from White Plains to Chicago in the evening. By choosing this option you can save up to 56% on the cost of your flight, compared to a flight in the afternoon.

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 November 19, 2025.

The most flights from HPN to CHI are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (5 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 November 19, 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
7.9
Good
8,003 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
7.9
Good
8,003 reviews
Delta
7.9
Good
8,003 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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
11,045 reviews
Delta
7.9
Good
8,003 reviews

Boarding

8.1

Entertainment

7.9

Overall

7.9

Food

7.3

Crew

8.5

Comfort

7.9

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 7 outbound flights to Chicago per day from 1 airline. White Plains Westchester County is conveniently located just 3.7 mi from White Plains’s city center.

  • How long is the flight from White Plains to Chicago?

    American Airlines and Delta can get you from White Plains to Chicago in just under 2h 43m. Your travel time can differ by up to 9h 19m. The distance between White Plains and Chicago is about 736 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What is the cheapest airline to fly from White Plains to Chicago round-trip?

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $349. Users have found that American Airlines is 27% 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: American Airlines (73%), Envoy Air (73%), Alaska Airlines( 71%).

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

    The cheapest flight price from White Plains to Chicago is $103. On average you can expect to pay $833. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $270.

  • 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, May is the cheapest month in which you can book a flight from White Plains to Chicago (average of $55). Flying from White Plains to Chicago in July is currently the most expensive (average of $126). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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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 airline flying from White Plains to Chicago

Discover the top airline 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 November 19, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$349Average$479FlexibilityNo cancel feeOn-time71%

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