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$157+ 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 12/17. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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The best prices from White Plains Westchester County to Chicago are usually found in January or February, booked 49 days in advance, depart on a Tuesday 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 November 20, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

December

Cheapest in

January

Round-trip from

$325
(American Airlines)

One-way from

$157
(Delta)
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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High demand for flights, 17% potential price rise
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Best time to find cheap flights, 29% potential price drop
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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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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 20, 2024.

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.
Tue 12/317:15 amHPN - ORD
Nonstop2h 34mAmerican Airlines
Fri 1/38:09 amORD - HPN
Nonstop2h 20mAmerican Airlines
Deal found 11/18$325
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/48:00 amHPN - ORD
2 stops17h 34mMultiple Airlines
Sun 12/84:19 pmORD - HPN
2 stops19h 11mMultiple Airlines
Deal found 11/19$333
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.
Fri 11/225:10 pmHPN - ORD
1 stop4h 15mDelta
Mon 11/256:00 amORD - HPN
1 stop7h 14mDelta
Deal found 11/19$383
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.
Tue 11/1912:30 pmHPN - MDW
1 stop5h 32mDelta
Sun 11/246:00 amMDW - HPN
1 stop5h 04mDelta
Deal found 11/19$450
This Mytrip deal was found by Cheapflights users on 11/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/212:00 pmHPN - MDW
3 stops21h 41mMultiple Airlines
Wed 12/49:30 amMDW - HPN
3 stops25h 20mMultiple Airlines
Deal found 11/20$1,049
This Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/45:10 pmHPN - MDW
3 stops26h 22mWestJet
Sun 12/89:38 amMDW - HPN
3 stops25h 12mWestJet
Deal found 11/19$1,532

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 2,629,791 searches. Data last updated November 20, 2024.

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Fly to

Any airport

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/31

7:15 am-8:49 am

Nonstop2h 34m

Chicago O'Hare Intl

Fri 1/3

8:09 am-11:29 am

Nonstop2h 20m

$325

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 1/9

8:20 am-8:13 pm

2 stops12h 53m

Chicago O'Hare Intl

Sat 1/11

5:10 am-12:30 pm

3 stops30h 20m

$326

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/17

12:45 pm-5:03 pm

1 stop5h 18m

Chicago Midway

Sat 5/24

9:30 am-4:33 pm

1 stop6h 03m

$348

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/17

12:59 pm-7:00 pm

1 stop7h 01m

Chicago O'Hare Intl

Sat 5/24

10:35 am-4:33 pm

1 stop4h 58m

$348

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 12/2

8:00 am-8:41 am

2 stops25h 41m

Chicago Midway

Wed 12/4

9:30 am-11:50 am

3 stops25h 20m

$775

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 12/4

5:10 pm-6:32 pm

3 stops26h 22m

Chicago Midway

Sun 12/8

9:38 am-11:50 am

3 stops25h 12m

$1,532

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/17

12:30 pm-9:24 am

1 stop21h 54m

$157

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/3

1:29 pm-10:17 am

2 stops21h 48m

$158

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 1/21

6:00 am-10:12 am

1 stop5h 12m

$174

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 12/10

6:00 am-6:00 pm

1 stop13h 00m

$217

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 12 results
1
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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 Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 November 15, 2024.

The best time to book flights from White Plains to Chicago is 49 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, September is the cheapest month in which you can book a flight from White Plains to Chicago (average of $232). Flying from White Plains to Chicago in June is currently the most expensive (average of $308). 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 20, 2024.

It’s optimal to fly from White Plains to Chicago in the afternoon. By choosing this option you can save up to 51% 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 November 20, 2024.

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 November 20, 2024.
Read reviews from past customers who have flown American Airlines, Delta and WestJet 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
8,756 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

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
8,756 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

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.

WestJet
7.3
Good
2,811 reviews
Delta
8.0
Very good
8,756 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

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
8,756 reviews

Crew

8.5

Comfort

7.9

Overall

8.0

Boarding

8.2

Entertainment

7.9

Food

7.3

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 $325. Additional round-trip tickets that might be worth considering are offered by Delta and WestJet, with the lowest prices starting at $348 and $1,532, respectively. Users have found that American Airlines is 27% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from White Plains to Chicago one-way?

    One-way options have recently been found by users for as low as $157 on Delta. Other airlines that offer cheap prices include American Airlines from $217 and WestJet from $419 one-way.

  • 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 (89%), American Airlines (83%), Envoy Air( 83%).

  • 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 $623. The most popular route, (White Plains Westchester County - Chicago O'Hare Intl), can usually be booked for $298.

  • 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, September is the cheapest month in which you can book a flight from White Plains to Chicago (average of $232). Flying from White Plains to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$177Average$345FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$276Average$471FlexibilityNo cancel feeOn-time71%
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