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$185+ Cheap flights from Westchester County 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
May 6 — May 131
Tue 5/6
Tue 5/13
1 adult, Economy
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Cheap flight deals from Westchester County to Chicago

Keep the following information in mind while searching for Westchester County to Chicago flight deals. Data was last updated May 1, 2025.

Most accurate provider

CheapOair
3 stars

Most trusted provider

CheapOair
3 stars

Round-trip from

$349
(American Airlines)

One-way from

$185
(Delta)

Popular in

December

Cheapest in

September

Average price

$249
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
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From Westchester County to Chicago (CHI)
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One-way flight from Westchester County to Chicago (CHI)
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Highest demand for flights based on searches. 2% potential increase in price ($6 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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Find flight deals from Westchester County to Chicago

Cheapest flights from Westchester County to Chicago
Explore the most affordable flight options available from Westchester County to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 1, 2025.

This American Airlines deal was found by Cheapflights users on 4/30. 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 5/2812:00 pmHPN - ORD
Nonstop2h 32mAmerican Airlines
Wed 6/412:49 pmORD - HPN
Nonstop2h 10mAmerican Airlines
Deal found 4/30$349
This Delta deal was found by Cheapflights users on 4/29. 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 8/1612:45 pmHPN - MDW
1 stop6h 43mDelta
Wed 8/206:00 amMDW - HPN
1 stop9h 04mDelta
Deal found 4/29$361
This Delta deal was found by Cheapflights users on 4/30. 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 5/244:29 pmHPN - ORD
1 stop18h 34mDelta
Thu 5/297:59 pmORD - HPN
1 stop15h 15mDelta
Deal found 4/30$361
This Mytrip deal was found by Cheapflights users on 4/30. 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 6/612:06 pmHPN - ORD
2 stops12h 23mMultiple Airlines
Sat 6/71:59 pmORD - HPN
1 stop21h 31mMultiple Airlines
Deal found 4/30$472

Cheapflights Fare Finder

Customize your flight search to find flights from Westchester County 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 May 1, 2025.
Use the filters below to find and compare flights from Westchester County to Chicago that are best for you.

Fly from

Westchester County

Fly to

Chicago

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 5/28

12:00 pm-1:32 pm

Nonstop2h 32m

Chicago O'Hare Intl

Wed 6/4

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 8/16

12:45 pm-6:28 pm

1 stop6h 43m

Chicago Midway

Wed 8/20

6:00 am-4:04 pm

1 stop9h 04m

$361

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/24

4:29 pm-10:03 am

1 stop18h 34m

Chicago O'Hare Intl

Thu 5/29

7:59 pm-12:14 pm

1 stop15h 15m

$361

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 6/6

12:06 pm-11:29 pm

2 stops12h 23m

Chicago O'Hare Intl

Sat 6/7

1:59 pm-12:30 pm

1 stop21h 31m

$472

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 7/29

12:55 pm-6:40 pm

1 stop6h 45m

$185

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 7/29

12:55 pm-4:33 pm

1 stop4h 38m

$185

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 6/13

6:00 am-7:30 am

Nonstop2h 30m

$201

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 6/6

12:06 pm-11:29 pm

2 stops12h 23m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/30

Best time to book a flight from Westchester County to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Westchester County 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 Westchester County to Chicago

What is the cheapest month to book a flight from Westchester County to Chicago?

Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County 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 REU to CHI?

Find hourly flight availability from Westchester County 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 May 1, 2025.

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

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 May 1, 2025.
See what other customers who have flown with Delta and American Airlines from Westchester County to Chicago have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
7,934 reviews
Delta
8.0
Very good
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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
7,934 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Comfort

7.9

Food

7.3

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 Westchester County to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Westchester County to Chicago?

    Consider Alaska Airlines (74%), American Airlines (73%) or Envoy Air (73%) when booking your flight. These represent the most reliable airlines when flying from Westchester County to Chicago.

  • What are the cheapest flights from Westchester County to Chicago?

    Looking for the cheapest flight from Westchester County to Chicago? While on average our users pay $628, our data indicates the cheapest price to be $137. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $266.

  • Can I find deals for flights from Westchester County to Chicago that include hotel bookings?

    Yes. In addition to deals on Westchester County to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Westchester County to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Westchester County to Chicago.

  • Can I find deals for business class flights from Westchester County to Chicago?

    Yes. Cheapflights offers flight deals from Westchester County 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 Westchester County to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $245). Flying from Westchester County 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 Westchester County?

Book flights to Westchester County if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Alternative routes for Westchester County 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 Westchester County to Chicago

Discover the top airline that operate flights from Westchester County 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 May 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$318Average$462FlexibilityNo cancel feeOn-time71%

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