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$100+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
1 adult, Economy
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The best prices from White Plains Westchester County to Chicago are usually found in March or September, booked 57 days in advance, depart on a Wednesday or Saturday and return on a Saturday

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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$328
(Delta)

One-way from

$100
(Mytrip)

Popular in

February

Cheapest in

March

Average price

$529

Good round-trip deal

$380 or less

Good one-way deal

$199 or less
Provider with most accurate pricing for White Plains Westchester County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for White Plains Westchester County-Chicago (CHI) flights.
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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. 2% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Delta deal was found by Cheapflights users on 2/20. 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.
lun. 3/244:29 pmHPN - MDW
2 stops17h 16mDelta
mar. 4/16:42 pmMDW - HPN
1 stop16h 13mDelta
Deal found 2/20$328
This Delta deal was found by Cheapflights users on 2/20. 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.
lun. 3/246:58 pmHPN - ORD
2 stops15h 20mDelta
mié. 4/26:45 amORD - HPN
1 stop8h 55mDelta
Deal found 2/20$328
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 3/312:00 pmHPN - ORD
3 stops25h 37mMultiple Airlines
jue. 3/66:15 amORD - HPN
3 stops29h 15mMultiple Airlines
Deal found 2/19$339
This American Airlines deal was found by Cheapflights users on 2/20. 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. 3/224:30 pmHPN - ORD
Nonstop2h 34mAmerican Airlines
sáb. 3/298:22 amORD - HPN
Nonstop2h 07mAmerican Airlines
Deal found 2/20$349

Find flights from White Plains to Chicago within your budget

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 febrero 20, 2025.

Fly from

White Plains

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

lun. 3/24

4:29 pm-8:45 am

2 stops17h 16m

Chicago Midway

lun. 3/31

6:42 pm-11:55 am

1 stop16h 13m

$328

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 3/24

6:58 pm-9:18 am

2 stops15h 20m

Chicago O'Hare Intl

lun. 3/31

6:45 am-4:40 pm

1 stop8h 55m

$328

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 3/3

12:00 pm-12:37 pm

3 stops25h 37m

Chicago O'Hare Intl

jue. 3/6

6:15 am-12:30 pm

3 stops29h 15m

$339

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 3/22

4:30 pm-6:04 pm

Nonstop2h 34m

Chicago O'Hare Intl

sáb. 3/29

8:22 am-11:29 am

Nonstop2h 07m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 3/10

8:00 am-6:26 pm

2 stops35h 26m

$100

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mar. 3/18

5:24 pm-12:41 pm

1 stop20h 17m

$154

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

vie. 3/14

12:35 pm-12:32 pm

1 stop24h 57m

$169

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sáb. 3/22

6:30 am-6:08 pm

2 stops12h 38m

$209

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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 February.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy1 starTrust 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

Travel insights for flights from White Plains to Chicago

Get recent, data-driven insights about flights from White Plains to Chicago including ideal travel times, pricing trends, and more.

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 February 14, 2025.

The best time to book flights from White Plains to Chicago is 57 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 febrero 20, 2025.

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 69% 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 febrero 20, 2025.

The most flights from HPN to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 febrero 20, 2025.
Read reviews from past customers who have flown Delta and American Airlines from White Plains to Chicago. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

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
8,219 reviews
Delta
8.0
Very good
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

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
8,219 reviews

Entertainment

7.9

Boarding

8.2

Overall

8.0

Comfort

8.0

Food

7.3

Crew

8.5

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 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 Delta is currently your cheapest option to Chicago, with prices starting at $328. Another option worth looking into is American Airlines, starting at $349 round trip. Users have found that Delta is 28% 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 (79%), American Airlines (73%), Envoy Air( 73%).

  • 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 $794. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $243.

  • 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 White Plains?

Book flights to White Plains if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$345FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$307Average$468FlexibilityNo cancel feeOn-time71%
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