HPN - CHI

$104 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 5/18. 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, 0 bags

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$236
Overall average: $452
Multiple Airlines
Tue 4/21Sun 4/26
HPN - ORD • 2 stops
Cheapest non-stop
$355
Typical prices: $410-$567
American Airlines
Wed 3/25Wed 4/1
HPN - ORD • Non-stop
Top airlines
American Airlines
Cheapest • from $355 (round-trip)
Delta
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Every day
You can fly direct with American Airlines. Average duration is 2h 47m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
HPN
-
ORD
Cheapest
HPN
-
ORD
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Detroit (DTW)
Cheapest • Avg $430 (round-trip)
Detroit (DTW)
Shortest trip • 4h 12m (one-way)
Insights
Insights
Insights
Insights
When to book
5 weeks
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 18% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
January
Cheapest • 10% price drop
July
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight 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

Tue, Apr 21 - Sun, Apr 26
Multiple Airlines Logo
12:08 pm - 8:03 am
HPN
-
ORD
20h 55m
2 stops
Multiple Airlines Logo
2:10 pm - 11:28 am
ORD
-
HPN
20h 18m
1 stop
$236Multiple Airlines
Mon, May 18 - Wed, May 20
Multiple Airlines Logo
6:09 pm - 11:16 pm
HPN
-
ORD
6h 07m
1 stop
Multiple Airlines Logo
1:27 pm - 11:27 am
ORD
-
HPN
21h 00m
2 stops
$250Multiple Airlines
Mon, May 11 - Wed, May 20
Multiple Airlines Logo
6:09 pm - 11:16 pm
HPN
-
ORD
6h 07m
1 stop
Multiple Airlines Logo
1:27 pm - 11:27 am
ORD
-
HPN
21h 00m
2 stops
$258Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
1:27 pm - 2:20 pm
HPN
-
ORD
25h 53m
2 stops
Multiple Airlines Logo
2:10 pm - 11:28 am
ORD
-
HPN
20h 18m
1 stop
$260Multiple Airlines
Mon, May 11 - Mon, May 18
Multiple Airlines Logo
6:09 pm - 11:16 pm
HPN
-
ORD
6h 07m
1 stop
Multiple Airlines Logo
3:31 pm - 11:27 am
ORD
-
HPN
18h 56m
2 stops
$263Multiple Airlines
Fri, May 15 - Wed, May 20
Multiple Airlines Logo
12:25 pm - 11:16 pm
HPN
-
ORD
11h 51m
1 stop
Multiple Airlines Logo
1:27 pm - 11:27 am
ORD
-
HPN
21h 00m
2 stops
$280Multiple Airlines
Fri, May 15 - Sun, May 17
Multiple Airlines Logo
12:25 pm - 11:16 pm
HPN
-
ORD
11h 51m
1 stop
Multiple Airlines Logo
8:24 pm - 5:29 pm
ORD
-
HPN
20h 05m
2 stops
$284Multiple Airlines
Fri, May 15 - Mon, May 18
Multiple Airlines Logo
12:25 pm - 11:16 pm
HPN
-
ORD
11h 51m
1 stop
Multiple Airlines Logo
3:31 pm - 11:27 am
ORD
-
HPN
18h 56m
2 stops
$285Multiple Airlines
Tue, Apr 21 - Wed, Apr 29
Delta Logo
12:30 pm - 5:58 pm
HPN
-
MDW
6h 28m
1 stop
Delta Logo
9:27 am - 3:49 pm
MDW
-
HPN
5h 22m
1 stop
$375Delta
Thu, Apr 23 - Sat, Apr 25
Delta Logo
12:48 pm - 10:28 pm
HPN
-
MDW
10h 40m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
HPN
5h 00m
1 stop
$391Delta
Booking Insights

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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from White Plains to Chicago costs $237 on the route between White Plains (HPN) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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 Saturday, 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 Saturday 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 January, where tickets cost $429 (return) on average. On the other hand, the most expensive months are December and October, where the average cost of round-trip tickets is $537 and $496 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.

No, with an average price for the route of $453, prices are generally cheapest when you fly direct.

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, which saves you about 18% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 4% 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 $104 for a one-way ticket and $236 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?

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

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

    The Embraer 175 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 $330 and an overall rating of 7.9, Delta is the most popular choice. American Airlines is also a great choice for the route, with an average price of $488 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 $167 or less one-way and $337 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.
7.9
DeltaOverall score based on 8237 reviews
7.8Entertainment
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
Airline reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

6.0 GoodAnthony, Feb 2026
LGA - CMH
Read more Delta reviews

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Flight delay was frustrating, also you cannot checkin online without delta app, web browser check-in throw errors

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Smooth boarding, pleasant and professional lady checking us in. Crew service was excellent, again pleasant, but professional. Nice touch-down on landing! Thank you Delta. 💗

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

We departed early and made up time in the air allowing us to arrive 30 minutes early. Capt was incredibly genuine and thanked every passenger for flying with Delta. Completely humble and professional!

Got on the plane and sat there for an hour before departure.

They double booked seats, the gate staff changed my ticket as I was boarding she went over to the computer and changed it without telling me. She messed up an entire three row section for me and others. Other travelers were outraged but the gate staff were so rude, so condescending saying it wasn't their problem to solve. I would rate this a zero if I could. Will not fly Delta again I'll stick with United and American.

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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

Information on your arrival and departure airports