HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$99+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Feb 4 — Feb 111
Wed 2/4
Wed 2/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from White Plains to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 Wednesday or Tuesday and return on a Tuesday

Cheap 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 January 5, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Fri 1/1612:08 pmHPN - ORD
2 stops12h 35mMultiple Airlines
Sun 1/187:45 amORD - HPN
1 stop26h 43mMultiple Airlines
Deal found 1/4$349
This American Airlines deal was found by Cheapflights users on 1/3. 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.
Tue 2/1712:00 pmHPN - ORD
Nonstop2h 43mAmerican Airlines
Tue 2/2412:50 pmORD - HPN
Nonstop2h 09mAmerican Airlines
Deal found 1/3$350
This Delta deal was found by Cheapflights users on 1/4. 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.
Tue 2/35:12 pmHPN - ORD
1 stop17h 29mDelta
Sat 2/75:35 pmORD - HPN
1 stop17h 23mDelta
Deal found 1/4$358
This American Airlines deal was found by Cheapflights users on 1/4. 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.
Wed 2/1811:28 amHPN - ORD
1 stop4h 49mAmerican Airlines
Wed 2/258:14 amORD - HPN
Nonstop2h 15mAmerican Airlines
Deal found 1/4$359
This Delta deal was found by Cheapflights users on 1/3. 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.
Wed 2/1810:28 amHPN - MDW
1 stop8h 17mDelta
Wed 2/256:00 amMDW - HPN
1 stop7h 28mDelta
Deal found 1/3$369
This Delta deal was found by Cheapflights users on 1/3. 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 4/113:13 pmHPN - ORD
1 stop5h 36mDelta
Tue 4/147:00 amORD - HPN
1 stop3h 44mDelta
Deal found 1/3$369
This Kiwi.com deal was found by Cheapflights users on 1/4. 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.
Fri 3/612:08 pmHPN - ORD
2 stops22h 45mMultiple Airlines
Sun 3/812:34 pmORD - HPN
1 stop21h 54mMultiple Airlines
Deal found 1/4$375
This American Airlines deal was found by Cheapflights users on 1/3. 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.
Wed 4/157:00 amHPN - ORD
Nonstop2h 38mAmerican Airlines
Sun 4/1912:39 pmORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 1/3$380
This Delta deal was found by Cheapflights users on 1/4. 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 1/3112:36 pmHPN - ORD
1 stop9h 29mDelta
Wed 2/46:00 pmORD - HPN
1 stop16h 58mDelta
Deal found 1/4$393
This Kiwi.com deal was found by Cheapflights users on 1/3. 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.
Thu 3/261:20 pmHPN - ORD
2 stops23h 27mMultiple Airlines
Sun 3/2912:34 pmORD - HPN
1 stop21h 54mMultiple Airlines
Deal found 1/3$395
This Delta deal was found by Cheapflights users on 1/4. 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 1/175:15 pmHPN - MDW
1 stop5h 52mDelta
Tue 1/206:00 amMDW - HPN
1 stop11h 00mDelta
Deal found 1/4$396
This Delta deal was found by Cheapflights users on 1/2. 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 4/136:44 pmHPN - ORD
1 stop14h 51mDelta
Sat 4/189:45 amORD - HPN
1 stop7h 19mDelta
Deal found 1/2$396

Find 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 January 5, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$349
(Kiwi.com)

One-way from

$99
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$483

Good round-trip deal

$380 or less

Good one-way deal

$304 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. 4% potential increase in price ($20 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 5, 2026.
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

Sat 2/14

12:36 pm-8:44 pm

1 stop9h 08m

Chicago O'Hare Intl

Tue 2/17

10:35 am-11:56 am

1 stop24h 21m

$358

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/14

11:29 am-4:45 pm

1 stop6h 16m

Chicago O'Hare Intl

Tue 3/17

1:58 pm-5:07 pm

Nonstop2h 09m

$359

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 2/17

12:56 pm-5:45 pm

1 stop5h 49m

Chicago Midway

Tue 2/24

9:50 am-4:32 pm

1 stop5h 42m

$369

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 2/18

10:28 am-5:45 pm

1 stop8h 17m

Chicago Midway

Wed 2/25

6:00 am-2:28 pm

1 stop7h 28m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 4/15

6:44 pm-11:57 pm

1 stop6h 13m

Chicago O'Hare Intl

Sat 4/18

9:45 am-6:04 pm

1 stop7h 19m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 4/14

3:10 pm-7:48 pm

1 stop5h 38m

Chicago O'Hare Intl

Sat 4/18

5:20 am-12:00 pm

1 stop5h 40m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 2/17

6:43 pm-11:56 pm

1 stop6h 13m

Chicago O'Hare Intl

Tue 2/24

9:52 am-6:00 pm

1 stop7h 08m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 2/18

3:15 pm-9:30 pm

1 stop7h 15m

Chicago O'Hare Intl

Wed 2/25

8:50 am-4:32 pm

1 stop6h 42m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 3/14

12:48 pm-8:02 pm

1 stop8h 14m

Chicago O'Hare Intl

Tue 3/17

11:10 am-6:18 pm

1 stop6h 08m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 1/31

12:36 pm-9:05 pm

1 stop9h 29m

Chicago O'Hare Intl

Wed 2/4

6:00 pm-11:58 am

1 stop16h 58m

$393

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/3

Showing 1-10 of 40 results
1
2
3
4

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 January.
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 January 2, 2026.

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, December is the cheapest month in which you can book a flight from White Plains to Chicago (average of $48). 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 January 5, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Chicago as you normally would.

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 January 5, 2026.
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
8,017 reviews

Entertainment

7.8

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

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
8,017 reviews
Delta
7.9
Good
8,017 reviews

Entertainment

7.8

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

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
11,079 reviews
Delta
7.9
Good
8,017 reviews

Entertainment

7.8

Crew

8.5

Boarding

8.1

Comfort

7.9

Food

7.2

Overall

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 4 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?

    Delta and American Airlines can get you from White Plains to Chicago in just under 6h 16m. Your travel time can differ by up to 2h 52m. 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 $356. Users have found that American Airlines is 25% 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: Qatar Airways (70%), American Airlines (70%), Envoy Air( 70%).

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

    The cheapest flight price from White Plains to Chicago is $169. On average you can expect to pay $609. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $369.

  • 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, December is the cheapest month in which you can book a flight from White Plains to Chicago (average of $48). 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
Merrillville
Hammond
Porter
Benton Harbor

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for White Plains to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to O'Hare Intl flights
Newark to O'Hare Intl flights
LaGuardia to O'Hare Intl flights
Newark to Midway flights
LaGuardia to Midway flights
John F Kennedy Intl to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Albany to O'Hare Intl flights
Syracuse to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Rochester to O'Hare Intl flights
Albany to Midway flights
White Plains to O'Hare Intl flights
Buffalo to Midway flights
Syracuse to Midway flights
White Plains to Midway flights
Rochester to Midway flights
Stewart to O'Hare Intl flights
Islip to O'Hare Intl flights
Ithaca to O'Hare Intl flights
Albany to St. Louis flights
Syracuse to St. Louis flights
Elmira to O'Hare Intl flights
Rochester to St. Louis flights
Buffalo to St. Louis flights
Elmira to Midway flights
Newark to Moline flights
Buffalo to Moline flights
John F Kennedy Intl to Moline flights
Newark to Peoria flights
LaGuardia to Moline flights
Newark to Bloomington flights
John F Kennedy Intl to Bloomington flights
Stewart to Rockford flights
John F Kennedy Intl to Evansville flights
Albany to Peoria flights
Ithaca to St. Louis flights
LaGuardia to Decatur flights
LaGuardia to Evansville flights
Watertown to O'Hare Intl flights
LaGuardia to Peoria flights
Ithaca to Midway flights
White Plains to St. Louis flights
Newark to Evansville flights
Albany to Moline flights
Syracuse to Peoria flights
Binghamton to O'Hare Intl flights

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 January 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$356Average$479FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.