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$126+ 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 1/23. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Jan 21 — Jan 281
Tue 1/21
Tue 1/28
1 adult, Economy
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The best prices from White Plains Westchester County to Chicago are usually found in September or November, booked 30 days in advance, depart on a Tuesday or Wednesday 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 January 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$320
(Mytrip)

One-way from

$126
(Mytrip)

Popular in

February

Cheapest in

September

Average price

$473
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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High demand for flights, 6% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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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 January 16, 2025.

This Mytrip deal was found by Cheapflights users on 1/16. 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.
Fri 1/318:00 amHPN - ORD
3 stops28h 20mMultiple Airlines
Tue 2/45:11 amORD - HPN
2 stops14h 19mMultiple Airlines
Deal found 1/16$320
This KAYAK deal was found by Cheapflights users on 1/15. 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.
Tue 2/115:09 pmHPN - ORD
2 stops16h 48mAmerican Airlines
Wed 2/1212:45 pmORD - HPN
Nonstop2h 05mAmerican Airlines
Deal found 1/15$329
This Delta deal was found by Cheapflights users on 1/15. 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 5/1312:59 pmHPN - MDW
1 stop6h 01mDelta
Tue 5/209:30 amMDW - HPN
1 stop6h 03mDelta
Deal found 1/15$369
This Delta deal was found by Cheapflights users on 1/15. 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.
Fri 2/145:24 pmHPN - ORD
1 stop4h 29mDelta
Wed 2/265:45 amORD - HPN
1 stop15h 28mDelta
Deal found 1/15$382

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 January 16, 2025.

Fly from

Any airport

Fly to

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Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 1/31

8:00 am-11:20 am

3 stops28h 20m

Chicago O'Hare Intl

Tue 2/4

5:11 am-8:30 pm

2 stops14h 19m

$320

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 2/11

5:09 pm-8:57 am

2 stops16h 48m

Chicago O'Hare Intl

Wed 2/12

12:45 pm-3:50 pm

Nonstop2h 05m

$329

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 5/13

12:59 pm-6:00 pm

1 stop6h 01m

Chicago Midway

Tue 5/20

9:30 am-4:33 pm

1 stop6h 03m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 2/14

5:24 pm-8:53 pm

1 stop4h 29m

Chicago O'Hare Intl

Wed 2/26

5:45 am-10:13 pm

1 stop15h 28m

$382

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 1/23

8:20 am-11:32 pm

2 stops16h 12m

$126

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 4/26

7:15 am-8:51 am

Nonstop2h 36m

$201

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/26

4:29 pm-10:29 pm

1 stop7h 00m

$211

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 4/26

5:10 pm-9:14 pm

1 stop5h 04m

$211

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
PricelinePrice Accuracy2 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 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 January 10, 2025.

The best time to book flights from White Plains to Chicago is 30 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 $320). 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 16, 2025.

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 67% 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 January 16, 2025.

The most flights from HPN to CHI are scheduled on a Monday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 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 January 16, 2025.
Read reviews from past customers who have flown American Airlines and Delta 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
8,511 reviews

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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
8,511 reviews
Delta
8.0
Very good
8,511 reviews

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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
8,511 reviews

Comfort

8.0

Entertainment

7.9

Boarding

8.2

Food

7.3

Overall

8.0

Crew

8.6

Reviews

1 / 10

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 6 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 American Airlines is currently your cheapest option to Chicago, with prices starting at $329. Another option worth looking into is Delta, starting at $369 round trip. Users have found that American Airlines is 29% 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%), Qatar Airways (74%), American Airlines( 72%).

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

    The cheapest flight price from White Plains to Chicago is $134. On average you can expect to pay $649. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $330.

  • 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 $320). 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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$148Average$345FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$304Average$474FlexibilityNo cancel feeOn-time71%
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