HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$197+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Jul 6 — Jul 131
Sun 7/6
Sun 7/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Westchester County 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.

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 July 1, 2025.

Round-trip from

$368
(Delta)

One-way from

$197
(Expedia)

Popular in

December

Cheapest in

September

Average price

$236
From Westchester County to Chicago (CHI)
Search Deals
One-way flight from Westchester County to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($3 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 July 1, 2025.

This Delta deal was found by Cheapflights users on 7/1. 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 7/196:49 pmHPN - ORD
1 stop6h 20mDelta
Tue 7/297:10 amORD - HPN
1 stop7h 33mDelta
Deal found 7/1$368
This Delta deal was found by Cheapflights users on 6/30. 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 10/1112:45 pmHPN - MDW
1 stop6h 51mDelta
Tue 10/146:00 amMDW - HPN
1 stop5h 11mDelta
Deal found 6/30$369
This American Airlines deal was found by Cheapflights users on 6/30. 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.
Fri 8/157:24 amHPN - ORD
Nonstop2h 36mAmerican Airlines
Tue 8/196:31 pmORD - HPN
Nonstop2h 28mAmerican Airlines
Deal found 6/30$380
This Mytrip deal was found by Cheapflights users on 7/1. 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 10/178:25 amHPN - ORD
2 stops11h 52mMultiple Airlines
Sun 10/197:39 pmORD - HPN
2 stops14h 49mMultiple Airlines
Deal found 7/1$461

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 July 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

Sat 7/19

6:49 pm-12:09 am

1 stop6h 20m

Chicago O'Hare Intl

Tue 7/29

7:10 am-3:43 pm

1 stop7h 33m

$368

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/11

12:45 pm-6:36 pm

1 stop6h 51m

Chicago Midway

Tue 10/14

6:00 am-12:11 pm

1 stop5h 11m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 8/15

7:24 am-9:00 am

Nonstop2h 36m

Chicago O'Hare Intl

Tue 8/19

6:31 pm-9:59 pm

Nonstop2h 28m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/17

8:25 am-7:17 pm

2 stops11h 52m

Chicago O'Hare Intl

Sun 10/19

7:39 pm-11:28 am

2 stops14h 49m

$461

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 7/23

9:45 am-10:33 pm

2 stops13h 48m

$197

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 10/9

6:30 am-3:58 pm

2 stops10h 28m

$205

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/24

8:25 am-7:17 pm

2 stops11h 52m

$222

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/10

4:00 pm-8:39 am

1 stop17h 39m

$324

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 7/8

12:55 pm-6:40 pm

1 stop6h 45m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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 July 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.

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 July 1, 2025.
See what other customers who have flown with Delta, JetBlue, and American Airlines from Westchester County to Chicago have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,973 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

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
8.0
Very good
7,973 reviews
Delta
8.0
Very good
7,973 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

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.
JetBlue
7.3
Good
2,919 reviews
Delta
8.0
Very good
7,973 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

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
10,000 reviews
Delta
8.0
Very good
7,973 reviews

Food

7.3

Comfort

7.9

Crew

8.5

Overall

8.0

Boarding

8.2

Entertainment

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 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 cheapest airlines to fly from Westchester County to Chicago one-way?

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $197. Users have also found prices from $205 and $314 on American Airlines and Delta, respectively.

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

    Consider American Airlines (82%), Envoy Air (82%) or Alaska Airlines (78%) 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 $1,955, our data indicates the cheapest price to be $159. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $265.

  • 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
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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 Westchester County 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
John F Kennedy Intl to Midway flights
LaGuardia to Midway flights
Newark to St. Louis flights
LaGuardia to St. Louis flights
John F Kennedy Intl to St. Louis flights
Rochester to O'Hare Intl flights
White Plains to O'Hare Intl flights
Albany to O'Hare Intl flights
Buffalo to O'Hare Intl flights
Stewart to O'Hare Intl flights
Syracuse to O'Hare Intl flights
White Plains to Midway flights
Rochester to Midway flights
Buffalo to Midway flights
Newark to Rockford flights
Albany to Midway flights
Syracuse to Midway flights
Syracuse to St. Louis flights
Albany to St. Louis flights
John F Kennedy Intl to Moline flights
Newark to Moline flights
Ithaca to O'Hare Intl flights
White Plains to St. Louis flights
Islip to O'Hare Intl flights
LaGuardia to Moline flights
Ithaca to St. Louis flights
LaGuardia to Peoria flights
John F Kennedy Intl to Springfield flights
Newark to Springfield flights
Newark to Peoria flights
John F Kennedy Intl to Peoria flights
Newark to Bloomington flights
LaGuardia to Bloomington flights
John F Kennedy Intl to Bloomington flights
Binghamton to O'Hare Intl flights
Rochester to St. Louis flights
LaGuardia to Champaign flights
Binghamton to Midway flights
Newark to Champaign flights
John F Kennedy Intl to Champaign flights
John F Kennedy Intl to Evansville flights
Buffalo to St. Louis flights
Elmira to O'Hare Intl flights
Newark to Evansville flights
White Plains to Bloomington flights

Top 2 airlines flying from Westchester County to Chicago

Discover the top 2 airlines 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 July 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$96Average$421FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$327Average$453FlexibilityNo 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.