HPN - CHI

$78 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 2/3. 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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Everything you should know

Cheapest round-trip
$300
Overall average: $451
Multiple Airlines
Tue 3/24Thu 3/26
HPN - ORD • 2 stops
Cheapest non-stop
$335
Typical prices: $391-$543
American Airlines
Tue 3/10Tue 3/17
HPN - ORD • Non-stop
Top routes
HPN-ORD
Cheapest
HPN-ORD
Most popular
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 19% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 7% 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, Mar 24 - Thu, Mar 26
Multiple Airlines Logo
12:08 pm - 11:38 pm
HPN
-
ORD
12h 30m2 stops
Multiple Airlines Logo
12:34 pm - 11:28 am
ORD
-
HPN
21h 54m1 stop
$300Multiple Airlines
Tue, Apr 14 - Mon, Apr 20
Delta Logo
12:30 pm - 8:40 pm
HPN
-
ORD
9h 10m1 stop
Delta Logo
7:43 pm - 11:44 am
ORD
-
HPN
15h 01m1 stop
$319Delta
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
4:30 pm - 6:18 pm
HPN
-
ORD
2h 48mnonstop
American Airlines Logo
8:14 am - 11:29 am
ORD
-
HPN
2h 15mnonstop
$335American Airlines
Sat, Apr 18 - Tue, Apr 21
Delta Logo
3:10 pm - 7:43 pm
HPN
-
ORD
5h 33m1 stop
Delta Logo
7:43 pm - 11:44 am
ORD
-
HPN
15h 01m1 stop
$337Delta
Fri, Apr 17 - Tue, Apr 21
Delta Logo
5:17 pm - 10:01 am
HPN
-
ORD
17h 44m1 stop
Delta Logo
7:43 pm - 11:44 am
ORD
-
HPN
15h 01m1 stop
$343Delta
Tue, Mar 10 - Tue, Mar 17
American Airlines Logo
5:37 pm - 7:25 pm
HPN
-
ORD
2h 48mnonstop
American Airlines Logo
10:28 am - 4:59 pm
ORD
-
HPN
5h 31m1 stop
$345American Airlines
Mon, Feb 9 - Tue, Feb 17
Delta Logo
5:12 pm - 8:52 am
HPN
-
MDW
16h 40m1 stop
Delta Logo
6:20 pm - 11:56 am
MDW
-
HPN
16h 36m1 stop
$347Delta
Mon, Feb 9 - Thu, Feb 19
Delta Logo
12:38 pm - 9:05 pm
HPN
-
ORD
9h 27m1 stop
Delta Logo
6:30 am - 3:49 pm
ORD
-
HPN
8h 19m1 stop
$347Delta
Mon, Feb 9 - Sat, Feb 21
Delta Logo
12:38 pm - 9:05 pm
HPN
-
ORD
9h 27m1 stop
Delta Logo
6:30 am - 11:56 am
ORD
-
HPN
4h 26m1 stop
$351Delta
Tue, Mar 10 - Tue, Mar 17
Delta Logo
12:35 pm - 4:43 pm
HPN
-
ORD
5h 08m1 stop
Delta Logo
9:50 am - 6:18 pm
ORD
-
HPN
7h 28m1 stop
$355Delta
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 $276 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 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 Tuesday 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 September, where tickets cost $450 (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.

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 $454 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, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$78
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 $78 for a one-way ticket and $300 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?

    American Airlines, Delta, and JetBlue 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 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 $483 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 $304 or less one-way and $380 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 8035 reviews
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

2.0 MediocreWilliam, Jan 2026
LGA - BOS
Read more Delta reviews

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

I truly love flying with Delta. They have always treated me with the upmost respect

The flight was great. The gate location was way to far away!!!

Cramped seating for me. Luckily it wasn’t a long flight

This route with Delta always has delays or is cancelled. Aircrafts seem smaller and older. I fly Delta quite a bit - haven’t had issues with the international flights. But this route has always been the troublesome one

Three seats in first class were broken and while they were able to still acommodate us it was looking very touch and go and they had others they could not acommodate

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

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Excellent - explanations were clear staff was nice and flight was comfortable

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

Information on your arrival and departure airports