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Cheap flights from Westchester County to Chicago

Compare Westchester County to Chicago flight deals

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Flight deals from Westchester County Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Westchester County Airport to Chicago? If you want to travel next month, return fares start from P24,192. Find the lowest prices on one-way and return tickets right here.
Chicago.P24,192 per passenger.Departing Wed, 15 Apr, returning Wed, 22 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Wed, 15 Apr, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 22 Apr, arriving in Westchester County.Price includes taxes and charges.From P24,192, select.
Chicago.P25,301 per passenger.Departing Sat, 4 Jul, returning Wed, 8 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Sat, 4 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 8 Jul, arriving in Westchester County.Price includes taxes and charges.From P25,301, select.
Chicago.P26,195 per passenger.Departing Fri, 19 Jun, returning Sat, 25 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Fri, 19 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 25 Jul, arriving in Westchester County.Price includes taxes and charges.From P26,195, select.
Chicago.P26,294 per passenger.Departing Sat, 23 May, returning Mon, 25 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Sat, 23 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 25 May, arriving in Westchester County.Price includes taxes and charges.From P26,294, select.
Chicago.P26,501 per passenger.Departing Sat, 13 Jun, returning Mon, 15 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Sat, 13 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 15 Jun, arriving in Westchester County.Price includes taxes and charges.From P26,501, select.
Chicago.P27,299 per passenger.Departing Fri, 14 Aug, returning Sat, 22 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Fri, 14 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 22 Aug, arriving in Westchester County.Price includes taxes and charges.From P27,299, select.
Chicago.P28,200 per passenger.Departing Thu, 30 Jul, returning Sun, 2 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Thu, 30 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 2 Aug, arriving in Westchester County.Price includes taxes and charges.From P28,200, select.
Chicago.P29,261 per passenger.Departing Wed, 18 Mar, returning Sat, 21 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Wed, 18 Mar, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 21 Mar, arriving in Westchester County.Price includes taxes and charges.From P29,261, select.
Chicago.P30,850 per passenger.Departing Thu, 26 Mar, returning Thu, 9 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Thu, 26 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Thu, 9 Apr, arriving in Westchester County.Price includes taxes and charges.From P30,850, select.
Chicago.P52,363 per passenger.Departing Fri, 9 Oct, returning Mon, 12 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Westchester County on Fri, 9 Oct, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 12 Oct, arriving in Westchester County.Price includes taxes and charges.From P52,363, select.

Find the cheapest month to fly from Westchester County to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Westchester County to Chicago flights are currently cheapest in April.
Mar
from P29,261
Apr
from P24,192
May
from P26,294
Jun
from P26,501
Jul
from P25,301
Aug
from P27,299
Sep
Find prices
Oct
from P52,363
Nov
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Dec
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Jan
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Feb
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Direct flights from Westchester County to Chicago

Alternative Westchester County to Chicago routes

Looking for the cheapest, fastest or easiest route from Westchester County to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
ClosestCheapest
from P24,192
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Chicago O'Hare International

25km from central Chicago
Cheapest
from P24,192
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

White Plains to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP24,192
Cheapest month to flyApril
Average flight time2 hrs, 45 mins
Most popular airlineEnvoy Air
Average flights per week105

Finding cheap flights from Westchester County to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Westchester County to Chicago is P24,192. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
2 hours and 45 minutes is the average flight time from Westchester County to Chicago.
American Airlines, Envoy Air and Alaska Airlines fly direct from Westchester County to Chicago.
As of March 2026, there are 210 flights per week flying from Westchester County to Chicago.
The cheapest month to fly from Westchester County to Chicago is usually April.
If you're flying from Westchester County Airport, the cheapest airport near Chicago is Chicago Midway – which is 14.5 km away from the centre of Chicago. We've found flights into this airport from P24,192.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Westchester County Airport to Chicago on Wednesday, 15 April 2026.
Yes – the average flight time is 2 hours and 45 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta offers the cheapest flight tickets to Chicago.

Travelling from Westchester County Airport (HPN) to Chicago: what you need to know

  • Approximately 2 hours 15 minutes is how long you can expect to be in the air on a direct flight from Westchester County Airport to Chicago.

  • Chicago is one hour behind White Plains, where Westchester County Airport is located. Chicago follows the UTC-5 timezone.

  • Westchester County Airport (HPN) to O'Hare International Airport (ORD) is the most popular route, with 25 departures a week to pick from. If you have things to do before leaving, the last flight from HPN to ORD is with American Airlines at 18:13. Choose the first departure operated by American Airlines at 06:00 if you want to fly out earlier.

  • Leave plenty of time to get on your HPN to Chicago flight. As a general rule, turn up at least two hours before international departures and an hour ahead for domestic flights.

  • Delays at check-in and security are more likely if you're jetting off during high season, so allow some extra breathing space. A good rule for peak times? Get there up to four hours early for international flights and two hours for domestic departures.

  • Start your journey at HPN and travel nonstop to O'Hare International Airport (ORD). That will be your arrival point when searching for Westchester County Airport to Chicago tickets.

  • Get on board with American Airlines. This airline operates direct flights from Westchester County Airport to Chicago.

  • From the centre of White Plains, HPN is around 11 kilometres away. Visit the official airport website or use navigation apps to work out the best way to reach the terminal.

  • Of the departures from Westchester County Airport, 74.52% land on time at their destination.

  • HPN is located at 240 Airport Road, Suite 202.

How to find the cheapest flights from Westchester County Airport (HPN) to Chicago

  • P9,396 is currently the lowest price for a one-way Westchester County Airport to Chicago flight. Return plane tickets start from P24,192. These fares can change based on demand.

  • To secure cheap flights from HPN to Chicago, reserve your journey one month ahead of your departure.

  • Organise your trip for May. That's the best month for scoring an awesome deal on Westchester County Airport to Chicago tickets. If you have flexibility with your dates, use the 'Whole month' tool to find the lowest price across every month.

  • Snapping up a cheap flight from HPN to Chicago couldn't be easier with Price Alerts. All you need to do is set up one of these automatic notifications and we'll get in touch as soon as a better deal is available.

  • Choose your preferred departure and arrival times, airlines and number of stops with our filters. Then, sort the results for your flight from Westchester County Airport to Chicago by 'Cheapest,' 'Fastest' or 'Best.'

Airports in Chicago

O'Hare International Airport (ORD)

  • The distance from O'Hare International Airport (ORD) to central Chicago is roughly 40 kilometres. It'll take you around 35 minutes to reach the centre driving.

  • If you're using public transport, expect a journey time of about 55 minutes.

  • Consider staying in a hotel close to ORD if you're coming in on a late flight from Westchester County Airport to Chicago. Select one of these accommodation options and make arrival day easier:

  • Go where the road takes you with an O'Hare International Airport rental car. Book your wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.

  • Reserving your ride from O'Hare International Airport around four weeks before your flight from HPN to Chicago can help you secure the lowest rate.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Chicago Midway International Airport (MDW) is around 19 kilometres from the centre of Chicago. After your flight from Westchester County Airport to Chicago, it'll take you around 20 minutes to get to the heart of the city in a ride-share or cab.

  • If you choose to travel on public transport, you'll get to the city centre in 45 minutes or so.

  • Hang the 'Do not disturb' sign on your door and relax at a hotel near MDW. Here are a few options where you can check in after your HPN to Chicago flight:

  • Dollar, Hertz and Budget make picking up a Chicago Midway International Airport rental car easy and quick. These suppliers are located in or around the terminal and will have you on your way in a heartbeat.

  • Avoid last-minute price surges. Securing your ride four weeks before your arrival at MDW will help you stay within budget.

  • You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is around 137 kilometres from the centre of Chicago. It takes about 1 hour 25 minutes to get to the city centre by car once you've stepped off your flight from Westchester County Airport to Chicago.

  • If you go by public transport, expect a journey of about 4 hours 15 minutes.

  • Stay at a hotel near RFD and go from landing to lounging in your room in a flash. Whether you're arriving on a late HPN to Chicago flight or just want a stress-free arrival, these accommodation options are all about convenience:

  • Take the guesswork out of the next leg of your trip with a Chicago Rockford International Airport rental car. Budget, Alamo and National make getting on the road effortless.

  • Booking a couple of weeks in advance of your flight from Westchester County Airport to Chicago is smart. As well as better prices, you'll likely have a better variety of makes and models to choose from at RFD.

  • The address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Before you book your flights from Westchester County Airport to Chicago, consider which time of year is best for you. High season in Chicago offers a lively atmosphere and plenty of activities, while low season means you'll get better deals on hotels and smaller crowds.

  • Before booking a Westchester County Airport to Chicago plane ticket, think about what kind of weather you prefer. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from HPN to Chicago in January if you like travelling in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago is always a good idea, but there are so many other corners of United States waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will keep your itinerary busy. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • Indianapolis is another sought-after destination in United States and is around 257 kilometres south-east of Chicago. No trip is complete without dropping by The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo.

Plan the rest of your trip from White Plains to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.