HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$124+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
Apr 7 — Apr 141
Tue 4/7
Tue 4/14
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

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 March 8, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/178:00 am
HPN
-
ORD
1 stop16h 16m
Multiple Airlines
Tue 5/194:28 pm
ORD
-
HPN
2 stops17h 49m
Multiple Airlines
Deal found 3/5$241
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/412:08 pm
HPN
-
ORD
1 stop11h 58m
Multiple Airlines
Thu 5/73:52 pm
ORD
-
HPN
2 stops24h 37m
Multiple Airlines
Deal found 3/4$262
This American Airlines deal was found by Cheapflights users on 3/5. 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 5/137:00 pm
HPN
-
ORD
2 stops13h 05m
American Airlines
Thu 5/148:10 am
ORD
-
HPN
Nonstop2h 19m
American Airlines
Deal found 3/5$292
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:08 pm
HPN
-
ORD
1 stop11h 58m
Multiple Airlines
Thu 4/231:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Deal found 3/5$308
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/156:09 pm
HPN
-
ORD
1 stop6h 07m
Multiple Airlines
Sun 5/178:24 pm
ORD
-
HPN
2 stops20h 05m
Multiple Airlines
Deal found 3/7$311
This Kiwi.com deal was found by Cheapflights users on 3/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:10 pm
HPN
-
ORD
2 stops23h 40m
Multiple Airlines
Thu 4/1612:16 pm
ORD
-
HPN
1 stop22h 12m
Multiple Airlines
Deal found 3/5$315
This Kiwi.com deal was found by Cheapflights users on 3/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:08 pm
HPN
-
ORD
1 stop12h 14m
Multiple Airlines
Sun 4/266:00 am
ORD
-
HPN
2 stops28h 28m
Multiple Airlines
Deal found 3/4$325
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:27 pm
HPN
-
ORD
2 stops34h 12m
Multiple Airlines
Sun 4/262:10 pm
ORD
-
HPN
1 stop20h 18m
Multiple Airlines
Deal found 3/6$328
This Delta deal was found by Cheapflights users on 3/3. 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.
Wed 7/2212:45 pm
HPN
-
MDW
1 stop6h 46m
Delta
Tue 7/289:20 am
MDW
-
HPN
1 stop6h 20m
Delta
Deal found 3/3$395
This Delta deal was found by Cheapflights users on 3/4. 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.
Mon 3/305:17 pm
HPN
-
MDW
1 stop16h 36m
Delta
Tue 4/76:34 pm
MDW
-
HPN
1 stop16h 19m
Delta
Deal found 3/4$409
This Delta deal was found by Cheapflights users on 3/4. 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 3/315:17 pm
HPN
-
MDW
1 stop16h 36m
Delta
Tue 4/76:34 pm
MDW
-
HPN
1 stop16h 19m
Delta
Deal found 3/4$410
This Delta deal was found by Cheapflights users on 3/7. 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 5/164:29 pm
HPN
-
MDW
1 stop5h 40m
Delta
Tue 5/199:23 am
MDW
-
HPN
1 stop6h 12m
Delta
Deal found 3/7$411

Find 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 March 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$241
(Kiwi.com)

One-way from

$124
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$249
Provider with most accurate pricing for New York (NYC)-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for New York (NYC)-Chicago (CHI) flights.
Search Deals
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. 11% potential increase in price ($31 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 March 2026
Search Deals

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 March 8, 2026.
Use the filters below to find and compare flights from Westchester County to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 7/22

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Tue 7/28

9:20 am-4:40 pm

1 stop6h 20m

$395

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 7/22

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Wed 7/29

9:20 am-4:40 pm

1 stop6h 20m

$395

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/27

5:10 pm-8:24 pm

1 stop4h 14m

Chicago O'Hare Intl

Wed 7/1

8:55 am-4:33 pm

1 stop6h 38m

$395

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 4/1

12:35 pm-8:17 pm

1 stop8h 42m

Chicago O'Hare Intl

Tue 4/7

7:10 am-3:48 pm

1 stop7h 38m

$409

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 3/31

5:17 pm-8:53 am

1 stop16h 36m

Chicago Midway

Tue 4/7

6:34 pm-11:53 am

1 stop16h 19m

$410

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 4/22

10:29 am-4:26 pm

1 stop6h 57m

Chicago Midway

Sat 4/25

6:00 am-2:29 pm

1 stop7h 29m

$411

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 6/13

12:45 pm-6:31 pm

1 stop6h 46m

Chicago Midway

Sat 6/20

9:20 am-4:40 pm

1 stop6h 20m

$411

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/13

5:10 pm-8:24 pm

1 stop4h 14m

Chicago O'Hare Intl

Sat 6/20

6:00 am-12:14 pm

1 stop5h 14m

$411

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 3/31

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

Wed 4/8

9:35 am-10:07 pm

2 stops11h 32m

$415

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/18

12:30 pm-5:58 pm

1 stop6h 28m

Chicago Midway

Mon 4/20

6:00 am-2:29 pm

1 stop7h 29m

$429

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/7

Showing 1-10 of 43 resultsSorted by cheapest first
1
2
3
...
5

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, February is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $117). Flying from Westchester County to Chicago in October is currently the most expensive (average of $380). 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 March 8, 2026.

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.

Weekly flight availability from Westchester County to Chicago

Explore weekly flight availability from Westchester County 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 March 8, 2026.

The most flights from zzREU to CHI are scheduled on a Wednesday (7 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (5 on average).

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 March 8, 2026.
See what other customers who have flown with Delta 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
7.9
Good
8,269 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

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
7.9
Good
8,269 reviews
Delta
7.9
Good
8,269 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

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
7.1
Good
11,397 reviews
Delta
7.9
Good
8,269 reviews

Comfort

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Overall

7.9

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 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.

  • How long is the flight from Westchester County to Chicago?

    A quick flight from Westchester County to Chicago can take about 6h 46m. Delta provides one of the quickest options available for as low as $395. There are 728 mi between Westchester County and Chicago.

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

    Consider American Airlines (83%), Envoy Air (83%) or Alaska Airlines (81%) 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 $714, our data indicates the cheapest price to be $143. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $245.

  • 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, February is the cheapest month in which you can book a flight from Westchester County to Chicago (average of $117). Flying from Westchester County to Chicago in October is currently the most expensive (average of $380). 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 Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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.

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 March 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$363Average$484FlexibilityNo 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.