HPN - CHI

$121 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 5/29. 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
$360
Typical prices: $590-$451
Multiple Airlines
Tue 5/5Thu 5/7
HPN - ORD • 2 stops
Cheapest non-stop
$395
Typical prices: $543-$380
American Airlines
Sat 8/1Sat 8/8
HPN - ORD • Non-stop
Top airlines
Cheapest • from $395 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with American Airlines. Average duration is 2h 50m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $430 (round-trip)
Shortest trip • 4h 12m (one-way)
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 5 weeks in advance save around 23% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 12% price drop
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, May 5 - Thu, May 7
Multiple Airlines Logo
8:00 am - 7:55 am
HPN
-
ORD
24h 55m
2 stops
Multiple Airlines Logo
8:39 am - 8:59 pm
ORD
-
HPN
11h 20m
1 stop
$360Multiple Airlines
Tue, Apr 28 - Thu, Apr 30
Multiple Airlines Logo
12:08 pm - 1:00 pm
HPN
-
ORD
25h 52m
2 stops
Multiple Airlines Logo
1:12 pm - 11:28 am
ORD
-
HPN
21h 16m
1 stop
$364Multiple Airlines
Mon, May 4 - Wed, May 6
Multiple Airlines Logo
12:08 pm - 11:06 pm
HPN
-
ORD
11h 58m
1 stop
Multiple Airlines Logo
1:59 pm - 8:59 pm
ORD
-
HPN
30h 00m
2 stops
$373Multiple Airlines
Mon, Apr 20 - Sun, Apr 26
Multiple Airlines Logo
12:08 pm - 11:06 pm
HPN
-
ORD
11h 58m
1 stop
Multiple Airlines Logo
5:50 am - 11:28 am
ORD
-
HPN
28h 38m
2 stops
$388Multiple Airlines
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
5:45 pm - 7:40 pm
HPN
-
ORD
2h 55mnonstop
American Airlines Logo
8:18 am - 11:28 am
ORD
-
HPN
2h 10mnonstop
$395American Airlines
Sat, Aug 1 - Sat, Aug 8
American Airlines Logo
6:00 am - 7:42 am
HPN
-
ORD
2h 42mnonstop
American Airlines Logo
5:21 pm - 11:24 pm
ORD
-
HPN
5h 03m
1 stop
$405American Airlines
Tue, Sep 8 - Sat, Sep 19
Delta Logo
12:45 pm - 6:31 pm
HPN
-
MDW
6h 46m
1 stop
Delta Logo
6:00 am - 12:13 pm
MDW
-
HPN
5h 13m
1 stop
$435Delta
Sat, Jun 6 - Mon, Jun 8
Delta Logo
12:31 pm - 6:33 pm
HPN
-
MDW
7h 02m
1 stop
Delta Logo
6:05 am - 12:09 pm
MDW
-
HPN
5h 04m
1 stop
$449Delta
Tue, Jun 30 - Fri, Jul 3
Delta Logo
12:35 pm - 6:31 pm
HPN
-
MDW
6h 56m
1 stop
Delta Logo
9:54 am - 4:30 pm
MDW
-
HPN
5h 36m
1 stop
$459Delta
Sat, Jun 27 - Tue, Jun 30
Delta Logo
12:35 pm - 6:06 pm
HPN
-
MDW
6h 31m
1 stop
Delta Logo
9:17 am - 3:49 pm
MDW
-
HPN
5h 32m
1 stop
$465Delta
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.

How much is a round-trip flight from White Plains to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from White Plains to Chicago departing in May.

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 $332 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 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 January, where tickets cost $429 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $537 and $523 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 $481 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 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$121
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 3% 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 $121 for a one-way ticket and $360 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, JetBlue, 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 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 $491 and an overall rating of 7.1.

  • 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 $265 or less one-way and $462 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 8392 reviews
7.8Entertainment
8.1Boarding
7.9Comfort
7.2Food
8.5Crew
Airline reviews

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

10.0 ExcellentKathryn, Apr 2026
JFK - LAX
Read more Delta reviews

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

I am still at the Airport! Delayed Delayed and Delyaed

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Delayed. Hot. Passenger next to me was so large I couldn’t move.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

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

Information on your arrival and departure airports