CHI - HPN

$93 Find Cheap Flights from Chicago to White Plains

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to White Plains departing on 4/26. 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 White Plains

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to White Plains, 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 Chicago to White Plains, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$355
Overall average: $456
American Airlines
Sat 8/15Sat 8/22
ORD - HPN • Non-stop
Cheapest one-way
$93
Typical prices: $269-$541
Multiple Airlines
Sun 4/26
ORD - HPN • 1 stop
Top airlines
American Airlines
Cheapest • from $355 (round-trip)
American Airlines
Best reviews • 7.1 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 13m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
ORD
-
HPN
Cheapest
ORD
-
HPN
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Atlanta (ATL)
Cheapest • Avg $265 (round-trip)
Detroit (DTW)
Shortest trip • 4h 04m (one-way)
Insights
Insights
Insights
Insights
When to book
7 weeks
in advance
Our data shows that travelers who book at least 7 weeks in advance save around 27% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
December
Cheapest • 10% price drop
March
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 White Plains!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to White Plains 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 Chicago to White Plains

Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
8:18 am - 11:28 am
ORD
-
HPN
2h 10mnonstop
American Airlines Logo
4:30 pm - 6:09 pm
HPN
-
ORD
2h 39mnonstop
$355American Airlines
Wed, Apr 8 - Wed, Apr 15
American Airlines Logo
12:32 pm - 3:48 pm
ORD
-
HPN
2h 16mnonstop
American Airlines Logo
4:30 pm - 6:25 pm
HPN
-
ORD
2h 55mnonstop
$356American Airlines
Sat, Aug 15 - Sat, Aug 22
American Airlines Logo
12:49 pm - 3:59 pm
ORD
-
HPN
2h 10mnonstop
American Airlines Logo
11:00 am - 3:48 pm
HPN
-
ORD
5h 48m
1 stop
$365American Airlines
Wed, Apr 8 - Wed, Apr 15
Multiple Airlines Logo
4:21 pm - 11:28 am
ORD
-
HPN
42h 07m
2 stops
Multiple Airlines Logo
1:27 pm - 5:27 pm
HPN
-
ORD
29h 00m
1 stop
$373Multiple Airlines
Sat, Aug 15 - Sat, Aug 22
Delta Logo
8:55 am - 4:33 pm
ORD
-
HPN
6h 38m
1 stop
Delta Logo
3:15 pm - 9:34 pm
HPN
-
ORD
7h 19m
1 stop
$375Delta
Wed, Mar 25 - Wed, Apr 1
Delta Logo
6:00 am - 12:03 pm
MDW
-
HPN
5h 03m
1 stop
Delta Logo
12:35 pm - 5:54 pm
HPN
-
MDW
6h 19m
1 stop
$375Delta
Mon, Mar 23 - Wed, Apr 1
Delta Logo
7:59 pm - 12:03 pm
ORD
-
HPN
15h 04m
1 stop
Delta Logo
5:17 pm - 8:17 pm
HPN
-
ORD
4h 00m
1 stop
$376Delta
Tue, Mar 24 - Tue, Mar 31
Delta Logo
12:47 pm - 10:07 pm
MDW
-
HPN
8h 20m
1 stop
Delta Logo
12:35 pm - 5:54 pm
HPN
-
MDW
6h 19m
1 stop
$376Delta
Mon, Mar 23 - Mon, Mar 30
Delta Logo
7:59 pm - 12:03 pm
ORD
-
HPN
15h 04m
1 stop
Delta Logo
6:59 pm - 8:30 am
HPN
-
ORD
14h 31m
1 stop
$377Delta
Wed, Mar 25 - Sat, Mar 28
American Airlines Logo
6:38 pm - 9:59 pm
ORD
-
HPN
2h 21mnonstop
American Airlines Logo
5:29 pm - 7:17 pm
HPN
-
ORD
2h 48mnonstop
$385American Airlines
Booking Insights

KAYAK's insights & trends for Chicago to White Plains flights

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

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

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

What is the cheapest Chicago to White Plains flight route?

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

The cheapest return flight from Chicago to White Plains costs $389 on the route between Chicago O'Hare Intl Airport (ORD) and White Plains (HPN). It is also the most popular route.

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

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

For Chicago to White Plains, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from White Plains back to Chicago, the best deals are generally found on Saturday, with Monday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to White Plains, 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 Chicago to White Plains is December, where tickets cost $411 (return) on average. On the other hand, the most expensive months are January and November, where the average cost of round-trip tickets is $519 and $496 respectively.

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

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 $423, prices are generally cheapest when you fly direct.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to White Plains, 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 Chicago to White Plains, you should book around 7 weeks before departure, which saves you about 27% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Find deals

Good to know

Low seasonJanuary
Cheapest flight$93
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago O'Hare Airport to White Plains

When to book flights from Chicago to White Plains

Are your dates flexible? Find out the best times to travel from Chicago to White Plains 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 Chicago to White Plains

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

    In the last 3 days, the lowest price for a flight from Chicago to White Plains was $93 for a one-way ticket and $355 for a round-trip.

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

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

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

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

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

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

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

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

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

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

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

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

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

    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 Chicago to White Plains.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to White Plains from Chicago 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 Chicago to White Plains?

    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 White Plains with an airline and back to Chicago with another airline.

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

    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 White Plains from Chicago 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 Chicago to White Plains

  • Looking for a cheap flight? 25% of our users found flights on this route for $289 or less one-way and $389 or less round-trip.

Prefer to fly direct from Chicago to White Plains?

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

Direct departures

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

Direct returns

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

Reviews of the top airline flying from Chicago to White Plains

 
See real verified KAYAK customer reviews for airlines flying from Chicago to White Plains. 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 Chicago to White Plains? 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.
7.1
American AirlinesOverall score based on 11345 reviews
6.4Food
8.0Crew
7.2Comfort
6.9Entertainment
7.5Boarding
Airline reviews

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

10.0 ExcellentBobby, Feb 2026
ORD - TPA
Read more American Airlines reviews

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

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

Information on your arrival and departure airports

White Plains (HPN)