HPN - CHI

$144 Find Cheap Flights from White Plains to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from White Plains to Chicago departing on 8/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from White Plains to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from White Plains to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from White Plains to Chicago (HPN-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from White Plains to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from White Plains to Chicago

Fri, Aug 8 - Sat, Aug 9
American Airlines Logo
5:29 pm - 5:37 amHPN-ORD
13h 08m2 stops
American Airlines Logo
8:17 am - 11:28 amORD-HPN
2h 11mnonstop
$269American Airlines
Find Deal
Tue, Aug 19 - Wed, Aug 27
Delta Logo
6:42 pm - 10:04 amHPN-ORD
16h 22m1 stop
Delta Logo
9:47 am - 10:23 pmORD-HPN
11h 36m1 stop
$277Delta
Find Deal
Wed, Aug 13 - Fri, Aug 15
Delta Logo
6:00 am - 4:28 pmHPN-ORD
11h 28m1 stop
Delta Logo
5:45 am - 4:34 pmORD-HPN
9h 49m1 stop
$284Delta
Find Deal
Wed, Aug 20 - Mon, Aug 25
Delta Logo
5:15 pm - 10:20 amHPN-ORD
18h 05m1 stop
Delta Logo
5:00 pm - 11:57 amORD-HPN
17h 57m1 stop
$297Delta
Find Deal
Mon, Aug 18 - Wed, Aug 27
Delta Logo
6:42 pm - 10:04 amHPN-ORD
16h 22m1 stop
Delta Logo
9:47 am - 10:23 pmORD-HPN
11h 36m1 stop
$298Delta
Find Deal
Sat, Aug 9 - Tue, Aug 12
Delta Logo
5:00 pm - 7:49 amHPN-ORD
15h 49m1 stop
Delta Logo
7:15 am - 3:49 pmORD-HPN
7h 34m1 stop
$302Delta
Find Deal
Sat, Aug 16 - Tue, Aug 26
Delta Logo
6:42 pm - 8:37 amHPN-ORD
14h 55m1 stop
Delta Logo
7:05 am - 6:02 pmORD-HPN
9h 57m1 stop
$305Delta
Find Deal
Tue, Aug 19 - Sat, Aug 23
Delta Logo
6:42 pm - 10:04 amHPN-ORD
16h 22m1 stop
Delta Logo
5:45 am - 2:29 pmORD-HPN
7h 44m1 stop
$323Delta
Find Deal
Tue, Aug 19 - Mon, Aug 25
Delta Logo
6:42 pm - 10:04 amHPN-ORD
16h 22m1 stop
Delta Logo
9:47 am - 10:23 pmORD-HPN
11h 36m1 stop
$327Delta
Find Deal
Sat, Aug 16 - Tue, Aug 19
American Airlines Logo
7:24 am - 9:00 amHPN-ORD
2h 36mnonstop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$349American Airlines
Find Deal
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KAYAK's insights & trends for White Plains to Chicago flights

Get data-powered insights and trends into flights from White Plains to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest White Plains to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from White Plains to Chicago.

Our data shows that the cheapest route for a return flight from White Plains to Chicago cost $334 and was between White Plains (HPN) and Chicago O'Hare Intl Airport (ORD). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $334.

What’s the cheapest day of the week to fly from White Plains to Chicago?

The average price of all round-trip flights from White Plains to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from White Plains to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Mondays for the best deals.

What is the cheapest month to fly from White Plains to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from White Plains to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from White Plains to Chicago is July, where tickets cost $416 (return) on average. On the other hand, the most expensive months are June and May, where the average cost of round-trip tickets is $494 and $486 respectively.

Can I save money by flying with a layover from White Plains to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $781 on average.

How far in advance should I book a flight from White Plains to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from White Plains to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from White Plains to Chicago, you should book around 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low seasonFebruary
High seasonSeptember
Cheapest flight$144
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from White Plains to Chicago O'Hare Airport

When to book flights from White Plains to Chicago

Are your dates flexible? Find out the best times to travel from White Plains to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from White Plains to Chicago

  • What is the cheapest flight from White Plains to Chicago?

    In the last 3 days, the lowest price for a flight from White Plains to Chicago was $144 for a one-way ticket and $269 for a round-trip.

  • Do I need a passport to fly between White Plains and Chicago?

    No

  • Which airports will I be using when flying from White Plains to Chicago?

    On your way to Chicago, you’ll fly out from White Plains Westchester County. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from White Plains to Chicago?

    Delta, JetBlue, American Airlines, Hawaiian Airlines, and Alaska Airlines offer inflight Wi-Fi service on the White Plains to Chicago flight route.

  • Which aircraft models fly most regularly from White Plains to Chicago?

    The Embraer 170 is the aircraft model that flies most regularly on the White Plains to Chicago flight route.

  • Which airline alliances offer flights from White Plains to Chicago?

    oneworld is the only airline alliance operating flights between White Plains and Chicago.

  • On which days can I fly direct from White Plains to Chicago?

    There are nonstop flights from White Plains to Chicago on a daily basis.

  • Which is the best airline for flights from White Plains to Chicago, Delta or American Airlines?

    The two airlines most popular with KAYAK users for flights from White Plains to Chicago are Delta and American Airlines. With an average price for the route of $281 and an overall rating of 8.0, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $452 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from White Plains to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from White Plains to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from White Plains to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from White Plains is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from White Plains to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to White Plains with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from White Plains to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from White Plains up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from White Plains to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $277 or less one-way and $408 or less round-trip.

Prefer to fly direct from White Plains to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from White Plains Westchester County to Chicago.
Find which airlines fly direct from White Plains Westchester County Airport to Chicago, which days they fly and book direct flights.

Direct departures

White Plains Westchester County to Chicago

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Direct returns

Chicago to White Plains Westchester County

Monday

American Airlines

American Airlines

Tuesday

American Airlines

American Airlines

Wednesday

American Airlines

American Airlines

Thursday

American Airlines

American Airlines

Friday

American Airlines

American Airlines

Saturday

American Airlines

American Airlines

Sunday

American Airlines

American Airlines

See more direct flights

Reviews of the top airlines flying from White Plains to Chicago

 
See real verified KAYAK customer reviews for airlines flying from White Plains to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from White Plains to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
DeltaOverall score based on 7952 reviews
7.3Food
8.2Boarding
7.9Comfort
7.9Entertainment
8.5Crew
Airline reviews

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

6.0 GoodAnonymous, Jul 2025JFK - LAS
Read more Delta reviews

At first, we were on the runway for about an hour, literally. The Captain did explain that the Control Tower just had a change shift (sounds like an unrealistic excuse) and then that we had to change a runway. A regular economy seat is made for 12 yo twiggy. I understand Delta wants to push for an upgrade, but after sitting in a Comfort seat and in First class. I would say First class is not worthy of my money. The landing was delayed because of the weather in NYC, I don't hold that against Delta, of course. The Captain did alert us to that upon takeoff in Vegas and again as we reached NY.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

I am very bothered by the events today. I can't believe the flight attendants allowed someone to take my seat and made me move. It was embarrassing. I was in the right. The lady just didn't want move. I can't believe delta would allow this to stand and disrespect my rights as a passenger. The lady complained about her leg and that she couldn't move. Firstly somehow she was able to make it to row 24. Not sure how much her leg could have hurt. Secondly, I'm in plenty of pain myself. I just finished chemotherapy a several weeks ago. My body is constantly sore. Yet deltas flight attendants didn't appropriately protect my rights. In the end they found me a seat on the plane but I want to understand how delta can operate this way. They in essence allowed a bully to get their way.

Terrible and im avoiding them in the future. My initial flight was delayed causing me to rebook my flight and when speaking with the representative to rebook I explained this is the second time my flights were delayed and they did nothing to help me. I wasn't booked to comfort plus or given a voucher or anything. I was almost late for my meeting that I needed to attend on Monday because of the games delta played delaying my flights even more and putting me in the very back of the plane next to an extremely intoxicated passenger

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Seats were really tight and the seat belts did not give enough slack.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

Everything you need to know for your flight from White Plains to Chicago

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