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$130+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
May 3 — May 101
Sun 5/3
Sun 5/10
1 adult, Economy
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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 April 3, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/108:00 am
HPN
-
ORD
1 stop5h 54m
Multiple Airlines
Tue 5/121:49 pm
ORD
-
HPN
2 stops29h 41m
Multiple Airlines
Deal found 3/29$356
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 4/151:27 pm
HPN
-
ORD
1 stop29h 00m
Multiple Airlines
Sun 4/198:52 pm
ORD
-
HPN
2 stops37h 36m
Multiple Airlines
Deal found 3/31$357
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:00 am
HPN
-
ORD
2 stops16h 07m
Multiple Airlines
Thu 4/301:12 pm
ORD
-
HPN
1 stop21h 16m
Multiple Airlines
Deal found 4/1$358
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:00 pm
HPN
-
ORD
1 stop25h 54m
Multiple Airlines
Mon 5/185:30 pm
ORD
-
HPN
2 stops16h 57m
Multiple Airlines
Deal found 3/30$372
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/108:00 am
HPN
-
ORD
1 stop5h 54m
Multiple Airlines
Sun 5/177:00 am
ORD
-
HPN
1 stop12h 59m
Multiple Airlines
Deal found 3/31$375
This Kiwi.com deal was found by Cheapflights users on 4/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:00 am
HPN
-
ORD
1 stop7h 39m
Multiple Airlines
Thu 5/145:49 pm
ORD
-
HPN
2 stops22h 40m
Multiple Airlines
Deal found 4/1$377
This Kiwi.com deal was found by Cheapflights users on 3/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:08 pm
HPN
-
ORD
1 stop12h 16m
Multiple Airlines
Sun 5/31:00 pm
ORD
-
HPN
2 stops21h 28m
Multiple Airlines
Deal found 3/29$391
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Sat 6/276:00 am
HPN
-
ORD
Nonstop2h 38m
American Airlines
Wed 7/16:03 pm
ORD
-
HPN
Nonstop2h 29m
American Airlines
Deal found 3/31$395
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Sat 5/212:00 pm
HPN
-
ORD
Nonstop2h 43m
American Airlines
Sat 5/912:30 pm
ORD
-
HPN
Nonstop2h 16m
American Airlines
Deal found 4/2$399
This Delta deal was found by Cheapflights users on 4/2. 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 5/212:30 pm
HPN
-
MDW
1 stop6h 28m
Delta
Sat 5/96:23 am
MDW
-
HPN
1 stop7h 06m
Delta
Deal found 4/2$415
This Delta deal was found by Cheapflights users on 3/31. 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 5/3012:31 pm
HPN
-
MDW
1 stop7h 02m
Delta
Sun 5/319:22 am
MDW
-
HPN
1 stop5h 27m
Delta
Deal found 3/31$449
This Delta deal was found by Cheapflights users on 3/29. 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 4/1812:30 pm
HPN
-
MDW
1 stop6h 28m
Delta
Tue 4/2112:52 pm
MDW
-
HPN
1 stop8h 11m
Delta
Deal found 3/29$475

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 April 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$356
(Kiwi.com)

One-way from

$130
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$239
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. 10% potential increase in price ($29 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 3, 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

Sat 5/2

6:00 am-10:14 am

1 stop5h 14m

Chicago Midway

Sat 5/9

6:23 am-2:29 pm

1 stop7h 06m

$415

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/27

5:10 pm-8:31 pm

1 stop4h 21m

Chicago O'Hare Intl

Wed 7/1

1:46 pm-10:25 pm

1 stop7h 39m

$415

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 7/11

12:35 pm-4:23 pm

1 stop4h 48m

Chicago O'Hare Intl

Tue 7/21

7:01 am-11:53 am

1 stop3h 52m

$415

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 7/21

10:29 am-4:44 pm

1 stop7h 15m

Chicago O'Hare Intl

Sat 7/25

3:35 pm-10:25 pm

1 stop5h 50m

$415

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 5/30

4:29 pm-9:09 pm

1 stop5h 40m

Chicago Midway

Mon 6/1

9:22 am-3:49 pm

1 stop5h 27m

$449
Quickest round-trip

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 6/6

5:15 pm-8:14 pm

1 stop3h 59m

Chicago O'Hare Intl

Sun 6/7

7:01 am-11:55 am

1 stop3h 54m

$449

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 7/8

6:49 pm-11:53 pm

1 stop6h 04m

Chicago O'Hare Intl

Sun 7/12

7:01 am-11:53 am

1 stop3h 52m

$449

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/18

12:30 pm-5:58 pm

1 stop6h 28m

Chicago Midway

Tue 4/21

12:52 pm-10:03 pm

1 stop8h 11m

$475

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 6/4

12:31 pm-6:33 pm

1 stop7h 02m

Chicago Midway

Mon 6/8

6:05 am-12:09 pm

1 stop5h 04m

$483

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 5/29

4:29 pm-9:09 pm

1 stop5h 40m

Chicago Midway

Sun 5/31

9:22 am-3:49 pm

1 stop5h 27m

$483

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 40 resultsSorted by cheapest first
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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 April 3, 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.

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 April 3, 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
8,374 reviews

Overall

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

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
7.9
Good
8,374 reviews
Delta
7.9
Good
8,374 reviews

Overall

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

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
7.1
Good
11,551 reviews
Delta
7.9
Good
8,374 reviews

Overall

7.9

Entertainment

7.8

Boarding

8.1

Food

7.2

Crew

8.5

Comfort

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.

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

    A quick flight from Westchester County to Chicago can take about 5h 14m. Delta provides one of the quickest options available for as low as $415. There are 728 mi between Westchester County and Chicago.

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

    Consider American Airlines (73%), Envoy Air (73%) or Alaska Airlines (71%) 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 $852, our data indicates the cheapest price to be $196. The most popular route (White Plains Westchester County - Chicago O'Hare Intl), is priced around $272.

  • 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

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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 April 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$374Average$489FlexibilityNo cancel feeOn-time71%

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