Cheap Flights from Westchester County NY to Chicago IL from $332

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Flight deals from Westchester County to Chicago

Looking for a cheap last-minute deal or the best round-trip flight from Westchester County Airport to Chicago? If you want to travel next month, round-trip fares start from $332. Find the lowest prices on one-way and round-trip tickets right here.

Chicago.$332 per passenger.Departing Wed, Jul 15, returning Wed, Jul 22.Round-trip flight with jetBlue and Frontier Airlines.Outbound indirect flight with jetBlue, departing from Westchester County on Wed, Jul 15, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Wed, Jul 22, arriving in Westchester County.Price includes taxes and charges.From $332, select.

Chicago.$333 per passenger.Departing Sat, Aug 15, returning Tue, Aug 18.Round-trip flight with jetBlue and Frontier Airlines.Outbound indirect flight with jetBlue, departing from Westchester County on Sat, Aug 15, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Tue, Aug 18, arriving in Westchester County.Price includes taxes and charges.From $333, select.

Chicago.$387 per passenger.Departing Wed, Sep 30, returning Sun, Oct 4.Round-trip flight with jetBlue and Allegiant Air.Outbound indirect flight with jetBlue, departing from Westchester County on Wed, Sep 30, arriving in Chicago Midway.Inbound indirect flight with Allegiant Air, departing from Chicago Rockford on Sun, Oct 4, arriving in Westchester County.Price includes taxes and charges.From $387, select.

Chicago.$387 per passenger.Departing Wed, Jul 29, returning Sat, Aug 1.Round-trip flight with jetBlue and Frontier Airlines.Outbound indirect flight with jetBlue, departing from Westchester County on Wed, Jul 29, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Sat, Aug 1, arriving in Westchester County.Price includes taxes and charges.From $387, select.

Chicago.$391 per passenger.Departing Wed, Jul 15, returning Wed, Jul 22.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Westchester County on Wed, Jul 15, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departing from Chicago O'Hare International on Wed, Jul 22, arriving in Westchester County.Price includes taxes and charges.From $391, select.

Chicago.$392 per passenger.Departing Tue, Jun 30, returning Mon, Jul 6.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Westchester County on Tue, Jun 30, arriving in Chicago Rockford.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Mon, Jul 6, arriving in Westchester County.Price includes taxes and charges.From $392, select.

Chicago.$396 per passenger.Departing Thu, Sep 10, returning Thu, Sep 17.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Westchester County on Thu, Sep 10, arriving in Chicago O'Hare International.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Thu, Sep 17, arriving in Westchester County.Price includes taxes and charges.From $396, select.

Chicago.$401 per passenger.Departing Wed, Jun 24, returning Sat, Jun 27.Round-trip flight with jetBlue and Allegiant Air.Outbound indirect flight with jetBlue, departing from Westchester County on Wed, Jun 24, arriving in Chicago Rockford.Inbound indirect flight with Allegiant Air, departing from Chicago Rockford on Sat, Jun 27, arriving in Westchester County.Price includes taxes and charges.From $401, select.

Chicago.$452 per passenger.Departing Wed, Jun 24, returning Sat, Jun 27.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Westchester County on Wed, Jun 24, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departing from Chicago O'Hare International on Sat, Jun 27, arriving in Westchester County.Price includes taxes and charges.From $452, select.

Chicago.$452 per passenger.Departing Fri, Oct 2, returning Tue, Oct 6.Round-trip flight with Breeze Airways and Frontier Airlines.Outbound indirect flight with Breeze Airways, departing from Westchester County on Fri, Oct 2, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departing from Chicago O'Hare International on Tue, Oct 6, arriving in Westchester County.Price includes taxes and charges.From $452, select.

Chicago.$468 per passenger.Departing Sat, Nov 21, returning Sun, Nov 22.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Westchester County on Sat, Nov 21, arriving in Chicago Midway.Inbound indirect flight with Delta, departing from Chicago Midway on Sun, Nov 22, arriving in Westchester County.Price includes taxes and charges.From $468, select.

Chicago.$595 per passenger.Departing Wed, Dec 23, returning Sun, Jan 3.Round-trip flight with Delta.Outbound indirect flight with Delta, departing from Westchester County on Wed, Dec 23, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departing from Chicago O'Hare International on Sun, Jan 3, arriving in Westchester County.Price includes taxes and charges.From $595, select.

Chicago.$908 per passenger.Departing Sun, Aug 30, returning Tue, Sep 1.Round-trip flight with American Airlines.Outbound direct flight with American Airlines departing from Westchester County on Sun, Aug 30, arriving in Chicago O'Hare International.Inbound direct flight with American Airlines departing from Chicago O'Hare International on Tue, Sep 1, arriving in Westchester County.Price includes taxes and charges.From $908, 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 July.

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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.

White Plains to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$332
Cheapest month to fly	July
Average flight time	2 hrs, 46 mins
Most popular airline	Envoy Air
Average flights per week	214

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

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are round-trip flights from Westchester County to Chicago?

The best price we found for a round-trip flight from Westchester County to Chicago is $332. 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.

How long does it take to fly from Westchester County to Chicago?

2 hours and 46 minutes is the average flight time from Westchester County to Chicago.

Which airlines fly direct from Westchester County to Chicago?

Envoy Air, American Airlines and Alaska Airlines fly direct from Westchester County to Chicago.

How many flights are there a week from Westchester County to Chicago?

There are 107 flights per week flying from Westchester County to Chicago, as of June 2026.

When is the cheapest time to fly from Westchester County to Chicago?

The cheapest month to fly from Westchester County to Chicago is usually July.

What's the cheapest airport to fly to in Chicago?

If you're flying from Westchester County Airport, the cheapest airport near Chicago is Chicago Rockford – which is 126.2 km away from the center of Chicago. We've found flights to this airport from $332.

Which upcoming date is cheapest to fly from Westchester County Airport to Chicago on?

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, July 15, 2026.

Can I get a direct flight from Westchester County Airport to Chicago?

Yes – the average flight time is 2 hours and 46 minutes.

How can I get the best flight deal from Westchester County Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°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.

Which is the cheapest airline to fly with from Westchester County Airport to Chicago?

Currently, jetBlue and American Airlines offer the cheapest flight tickets to Chicago.

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

The average time for a direct flight from Westchester County Airport to Chicago is 2 hours 15 minutes.
Westchester County Airport is located in White Plains. Following the UTC-6 timezone, Chicago is one hour behind White Plains.
With 27 flights a week between the two airports, Westchester County Airport (HPN) to Chicago O'Hare International Airport (ORD) is the busiest route. American Airlines operates the earliest flight at 06:00. If you prefer to make the most of your day before jetting off, the last departure from HPN to ORD is with American Airlines at 18:13.
For hassle-free travel, arrive at the airport two hours ahead of international flights and one hour before domestic departures. This ensures you have enough time to catch your HPN to Chicago flight.
Traveling during a peak month such as July? School holidays and other high seasons can lead to longer queues at security. Play it safe and arrive up to four hours before international flights and two hours before a domestic departure.
You can book a direct Westchester County Airport to Chicago ticket. Begin your trip at HPN and land at Chicago O'Hare International Airport (ORD).
Get on board with American Airlines. This airline operates direct flights from Westchester County Airport to Chicago.
Located around 11 kilometers from central White Plains, HPN can be reached in about 10 minutes by car. The journey on public transport will take roughly 25 minutes.
Need a convenient place to stay before your flight from Westchester County Airport to Chicago? Doral Arrowwood and Ibm Learning Center are near HPN. They're an especially great choice if you have an early departure.
When it comes to the on-time performance of Westchester County Airport, 73% of flights complete their journey on time.
HPN is located at 240 Airport Road, Suite 202.

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

$167 is currently the best price for a one-way Westchester County Airport to Chicago flight. Return plane tickets start at $332. These prices can change depending on availability and demand.
To find cheap flights from HPN to Chicago, book in advance. Airlines tend to offer lower prices when flights first go on sale.
The 'Whole month' tool will show you the cheapest tickets from Westchester County Airport to Chicago throughout the month. It's an easy way to snap up a bargain if your travel plans are flexible.
There's no need to keep checking in to find out if fares have dropped when you set up a Price Alert. We'll notify you as soon as there's an even better deal on cheap flights from HPN to Chicago.
Choose your preferred arrival and departure times, airlines and number of stops with our filters. Then, sort the results for your flight from Westchester County Airport to Chicago by 'Fastest,' 'Cheapest' or 'Best.'

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to the center of Chicago takes around 30 minutes by car. The center is roughly 27 kilometers away.
Getting there on public transport takes about 45 minutes.
The last thing you need is a long journey to your hotel if you're arriving on a late flight from Westchester County Airport to Chicago. Stay at one of these accommodation options near ORD instead:
Booking your vehicle from Chicago O'Hare International Airport about four weeks before your flight from HPN to Chicago can help you lock in the lowest rate.
You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

Once your flight from Westchester County Airport to Chicago has landed, you can get to the city center in around 25 minutes by car. Central Chicago is roughly 16 kilometers from Chicago Midway International Airport (MDW).
If you choose to travel on public transport, the ride to the center takes 30 minutes or so.
Following your HPN to Chicago flight, settle in at a hotel close to MDW. These are some comfortable accommodation options that'll help you get into relaxation mode:
Avoid last-minute price surges. Booking your ride four weeks ahead of your arrival at MDW can get you a lower rate.
You'll find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Hop off your flight from Westchester County Airport to Chicago and head straight for your hotel or start sightseeing right away. The center of Chicago is around 145 kilometers from Chicago Rockford International Airport (RFD) and typically takes 1 hour 40 minutes to drive there.
Public transport will get you there in about 2 hours.
Reserve a hotel close to RFD and go from the runway to resting in a snap. Whether you're coming in on a late HPN to Chicago flight or just want to simplify your travel plans, these accommodation options offer a quick route to a good night's sleep:
If you prefer a particular kind of vehicle, booking early increases your chances of finding what you want. Secure your ride from RFD at least a couple of weeks ahead of your flight from Westchester County Airport to Chicago.
Chicago Rockford International Airport is located at 2 Airport Cir.

Best time to go to Chicago

It's time to plan your trip dates for your flight from Westchester County Airport to Chicago. July is the busiest month to travel to Chicago. If you like a more low-key vibe, go in January.
When booking your Westchester County Airport to Chicago plane ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).
Search for cheap tickets from HPN to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

After booking your flight from Westchester County Airport to Chicago, choose a hotel that puts you where you want to be. Make one of these accommodation options your base for exploring Chicago:
Art Institute of Chicago and Millennium Park are just two of the top-rated attractions to add to your Chicago itinerary. Keep the sightseeing going at Willis Tower.

Explore more of the United States

Columbus is just one of the many cities in the United States waiting to be discovered after you've seen Chicago. Around 451 kilometers away to the southeast, its best attractions include Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theater.
Indianapolis is another favorite destination in the United States and is around 257 kilometers southeast of Chicago. No trip is complete without seeing Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.