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HPN - CHI

$106 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 6/17. 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
0 bags
Thu 6/13
Thu 6/20

Search 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
In the last 7 days travelers have searched 42,566,405 times on KAYAK, and here is why:

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

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

Bundle and saveSave money when you bundle your flight + hotel.

Cheap flight deals from White Plains to Chicago (HPN-CHI)

 
These are the cheapest deals for flights from White Plains to Chicago currently on KAYAK along with options from the most popular airlines KAYAK users selected for this route. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from White Plains to Chicago

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from White Plains to Chicago.

Recent one-way flight deals from White Plains to Chicago

Only flying one-way? Below are some of the best one-way flight deals from White Plains to Chicago found on KAYAK recently.

Recent last minute flight deals from White Plains to Chicago

Leaving soon but still want a bargain? Check out these latest deals for last minute flights from White Plains to Chicago.

Recent direct flight deals from White Plains to Chicago

The latest deals for direct flights from White Plains to Chicago so you can sit back and relax without the need for a layover.

Cheap bus & train deals from White Plains to Chicago

Find recent round-trip train or bus tickets from White Plains to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
6:00 am - 9:38 pmHPN-ORD
16h 38m1 stop
7:10 am - 11:47 amORD-HPN
3h 37m1 stop
$290Delta
Find Deal
Tue, Jun 18 - Tue, Jun 25
7:49 pm - 8:35 pmHPN-ORD
25h 46m3 stops
7:07 pm - 12:30 pmORD-HPN
16h 23m2 stops
Fri, May 31 - Sun, Jun 2
7:49 pm - 8:35 pmHPN-ORD
25h 46m3 stops
9:35 am - 7:08 pmORD-HPN
32h 33m3 stops
Fri, May 31 - Tue, Jun 4
6:00 am - 5:59 pmHPN-MDW
12h 59m1 stop
3:45 pm - 10:21 pmMDW-HPN
5h 36m1 stop
$310Delta
Find Deal
Tue, Jun 18 - Tue, Jun 25
6:45 pm - 8:04 amHPN-ORD
14h 19m1 stop
10:15 am - 4:45 pmORD-HPN
5h 30m1 stop
$310Delta
Find Deal
Sat, Jun 22 - Tue, Jun 25
6:00 am - 9:46 pmHPN-MDW
16h 46m1 stop
9:24 am - 4:45 pmMDW-HPN
6h 21m1 stop
$311Delta
Find Deal
Sat, Jul 6 - Sat, Jul 13
6:00 am - 7:47 pmHPN-ORD
14h 47m1 stop
10:20 am - 4:45 pmORD-HPN
5h 25m1 stop
$311Delta
Find Deal
Sat, Jul 6 - Sat, Jul 13
5:25 pm - 10:46 amHPN-ORD
18h 21m2 stops
12:51 pm - 3:59 pmORD-HPN
2h 08mnonstop
$413American Airlines
Find Deal
Wed, May 29 - Thu, May 30
7:04 am - 8:35 amHPN-ORD
2h 31mnonstop
12:05 pm - 10:43 pmORD-HPN
9h 38m2 stops
$432American Airlines
Find Deal
Wed, May 29 - Wed, May 29
5:29 pm - 11:02 amHPN-MDW
18h 33m3 stops
9:46 am - 11:52 amMDW-HPN
25h 06m3 stops
$1,585WestJet
Find Deal
Fri, May 24 - Mon, May 27
1:10 pm - 10:01 amHPN-ORD
21h 51m2 stops
Mon, Jun 17
12:45 pm - 4:13 pmHPN-MDW
4h 28m1 stop
$113Delta
Find Deal
Sat, Jun 1
6:45 pm - 11:56 pmHPN-ORD
6h 11m1 stop
$113Delta
Find Deal
Tue, Jun 11
1:10 pm - 9:55 amHPN-ORD
21h 45m2 stops
Mon, May 20
1:10 pm - 9:55 amHPN-ORD
21h 45m2 stops
Fri, May 31
7:40 pm - 10:53 pmHPN-ORD
28h 13m3 stops
Tue, Jun 11
6:30 am - 1:42 pmHPN-ORD
8h 12m1 stop
$245American Airlines
Find Deal
Tue, Jun 18
7:20 am - 8:53 amHPN-ORD
2h 33mnonstop
$278American Airlines
Find Deal
Tue, Jun 18
10:05 am - 2:11 pmHPN-ORD
5h 06m1 stop
$286American Airlines
Find Deal
Thu, Jul 25
12:29 pm - 2:00 pmHPN-ORD
2h 31mnonstop
$307American Airlines
Find Deal
Sun, Jun 2
10:05 am - 2:20 pmHPN-ORD
5h 15m1 stop
8:09 am - 11:27 amORD-HPN
2h 18mnonstop
$624American Airlines
Find Deal
Sun, May 19 - Sun, Jun 9
12:45 pm - 5:06 pmHPN-MDW
5h 21m1 stop
6:00 am - 12:03 pmMDW-HPN
5h 03m1 stop
$646Delta
Find Deal
Sun, May 19 - Sun, Jun 9
12:45 pm - 6:17 pmHPN-ORD
6h 32m1 stop
11:59 am - 4:49 pmORD-HPN
3h 50m1 stop
$668Delta
Find Deal
Thu, May 16 - Sun, May 26
12:29 pm - 2:00 pmHPN-ORD
2h 31mnonstop
12:51 pm - 3:59 pmORD-HPN
2h 08mnonstop
$678American Airlines
Find Deal
Thu, May 16 - Sun, May 26
12:29 pm - 2:00 pmHPN-ORD
2h 31mnonstop
3:20 pm - 10:43 pmORD-HPN
6h 23m1 stop
$686American Airlines
Find Deal
Thu, May 16 - Mon, May 20
4:30 pm - 6:01 pmHPN-ORD
2h 31mnonstop
12:51 pm - 3:59 pmORD-HPN
2h 08mnonstop
$689American Airlines
Find Deal
Wed, May 15 - Sat, May 18
6:00 am - 10:26 amHPN-ORD
5h 26m1 stop
1:40 pm - 8:28 pmORD-HPN
5h 48m1 stop
$694American Airlines
Find Deal
Thu, May 16 - Mon, May 20
7:04 am - 8:35 amHPN-ORD
2h 31mnonstop
7:30 am - 1:10 pmORD-HPN
4h 40m1 stop
$697American Airlines
Find Deal
Thu, May 16 - Sun, May 19
6:00 am - 12:40 pmHPN-ORD
7h 40m1 stop
8:30 am - 4:55 pmORD-HPN
7h 25m1 stop
$705American Airlines
Find Deal
Thu, May 16 - Sun, May 19
1:10 pm - 11:29 pmHPN-ORD
11h 19m2 stops
7:07 pm - 12:30 pmORD-HPN
16h 23m2 stops
Fri, May 17 - Sun, May 19
7:29 am - 9:00 amHPN-ORD
2h 31mnonstop
12:48 pm - 3:59 pmORD-HPN
2h 11mnonstop
$440American Airlines
Find Deal
Wed, Jul 31 - Wed, Jul 31
4:30 pm - 6:03 pmHPN-ORD
2h 33mnonstop
6:37 pm - 9:59 pmORD-HPN
2h 22mnonstop
$445American Airlines
Find Deal
Wed, Jun 12 - Wed, Jun 19
4:30 pm - 6:01 pmHPN-ORD
2h 31mnonstop
8:09 am - 11:27 amORD-HPN
2h 18mnonstop
$455American Airlines
Find Deal
Tue, Jun 4 - Mon, Jun 10
4:30 pm - 6:03 pmHPN-ORD
2h 33mnonstop
8:09 am - 11:27 amORD-HPN
2h 18mnonstop
$465American Airlines
Find Deal
Fri, Jun 14 - Mon, Jun 17
12:19 pm - 1:52 pmHPN-ORD
2h 33mnonstop
6:37 pm - 9:59 pmORD-HPN
2h 22mnonstop
$470American Airlines
Find Deal
Wed, Jun 5 - Fri, Jun 7
7:04 am - 8:35 amHPN-ORD
2h 31mnonstop
12:52 pm - 3:59 pmORD-HPN
2h 07mnonstop
$479American Airlines
Find Deal
Sat, Jun 1 - Sat, Jun 8
12:23 pm - 1:54 pmHPN-ORD
2h 31mnonstop
8:09 am - 11:27 amORD-HPN
2h 18mnonstop
$489American Airlines
Find Deal
Sat, Jun 1 - Sun, Jun 9
7:29 am - 9:00 amHPN-ORD
2h 31mnonstop
8:09 am - 11:29 amORD-HPN
2h 20mnonstop
$495American Airlines
Find Deal
Thu, Jul 18 - Fri, Jul 19
7:04 am - 8:35 amHPN-ORD
2h 31mnonstop
12:51 pm - 3:59 pmORD-HPN
2h 08mnonstop
$513American Airlines
Find Deal
Tue, May 28 - Wed, May 29
7:20 am - 8:53 amHPN-ORD
2h 33mnonstop
8:09 am - 11:27 amORD-HPN
2h 18mnonstop
$529American Airlines
Find Deal
Tue, Jun 18 - Sun, Jun 23

Flights from White Plains to Chicago - Travel Insights & Trends

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 one-way flights from White Plains to Chicago.
Our data shows that the cheapest route for a one-way flight from White Plains to Chicago cost $126 and was between White Plains and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is $283.

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

The average price of all flights from White Plains to Chicago clicked on KAYAK for each day over the last 12 months.
For White Plains to Chicago, Wednesday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Chicago back to White Plains, the best deals are generally found on Wednesday, with Monday being the most expensive.

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 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 February, where tickets cost $195 on average. On the other hand, the most expensive months are June and July, where the average cost of tickets is $348 and $308 respectively.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from White Plains to Chicago, you should book around 3 weeks before departure. For the absolute cheapest price, our data suggests you should book 77 days before departure.

Which airlines provide the cheapest flights from White Plains to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The cheapest return flight ticket from White Plains to Chicago found by KAYAK users in the last 72 hours was for $290 on Delta, followed by American Airlines ($413). One-way flight deals have also been found from as low as $113 on Delta and from $245 on American Airlines.

Which airlines fly non-stop between White Plains and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from White Plains to Chicago.
There is just one airline that flies from White Plains to Chicago direct and that is American Airlines. The best one-way deal found from American Airlines for the route is $236.

How many flights are there between White Plains and Chicago per day?

Each day, there are 3 nonstop flights that take off from White Plains and land in Chicago, with an average flight time of 2h 31m. The most common departure time is 4:00 pm and most flights take off in the morning. Each week, there are 21 flights and there are the same amount of flights each day 3.

Which cabin class options are there for flights between White Plains and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from White Plains to Chicago take?

Direct flights cover the 722 miles separating White Plains to Chicago in about 2h 31m.

What’s the earliest departure time from White Plains to Chicago?

Early birds can take the earliest flight from White Plains at 7:04 am and will be landing in Chicago at 8:35 am.

What’s the latest departure time from White Plains to Chicago?

If you prefer to fly at night, the latest flight from White Plains to Chicago jets off at 4:30 pm and lands at 6:01 pm.

Good to know

Low season

January

High season

June

Cheapest flight

$106
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 7% 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 $106 for a one-way ticket and $290 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?

    JetBlue, Delta, American 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 $381 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 $455 and an overall rating of 7.3.

  • 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.

See more FAQs

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 $216 or less one-way and $412 or less round-trip.

Prefer to fly non-stop from White Plains to Chicago?

Find which airlines fly direct from Westchester County to Chicago, which days they fly and book direct flights.

Nonstop departures

White Plains Westchester County to Chicago

Monday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Tuesday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Wednesday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Thursday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Friday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Saturday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Sunday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

See more direct flights

Nonstop returns

Chicago to White Plains Westchester County

Monday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Tuesday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Wednesday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Thursday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Friday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Saturday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

Sunday

Alaska Airlines, American Airlines, Qatar Airways

Alaska Airlines, American Airlines, +1 more

See more direct flights
See more direct flights

Top 3 airlines serving 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 10706 reviews
8.2Boarding
7.4Food
7.9Comfort
8.0Entertainment
8.6Crew
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Seat back monitors and outlets were dead and not working.

I usually have a positive experience with Delta. Complimentary upgrades are always nice!

It was a crowded flight. They did the best they could.

Service was good for such a short flight. Small plane but smooth flight.

The flight was delayed but we got to our final destination.

Uncomfortable seats on 14 hour flight. Mediocre food. On time and great crew.

The helpful attitude of the staff, and being a wheelchair passenger everyone was helpful and understanding. The trip was made comfortable by the upgraded seat which was given without my request, that was a great surprise. Thank you Delta.

We just spent $6000 on our first trip since pre COVID and we were stranded on the runway of our departing airport for 2 hours and 15 minutes while our layover was only an hour and a half. We were told by the pilot we were next for de-icing and then got bumped by 3 other planes. Pilot went on to say they only had one guy working the de-icing where they usually have at least 2. In Rochester. In the heart of winter. Someone missed a step and should be fired. I'm not done.

Everything went well with the flight. But one of the flight attendants had on inappropriate pants. She had on an old worn out pair of sweat pants. The back seam was unrivaled and should not have been worn for work. If I had not seen her in the airport with the standard type of luggage, I certainly would not have thought she was working for Delta. Not a good look at all for representation.

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Awful…flight was delayed more than 12hrs, missed all connections to Fort Wayne, IN, had to get flight to another city 2 hours from my destination, flight was again delayed by 40 mins because they did not have enough fuel, again missed a connection, finally arrived in Indiana at 11pm…but before my 2 hour drive home, ay, no Five That Our Luggage Never Made On The plane and Still In Chicago

Boarding was friendly and quick. While the plane model was older with no live tv, the entertainment was full of movies and tv shows. All food was available. Pilots were very communicative with status of the flight. Flight landed on time.

The Palm Springs to Chicago O’Hare was on Time and Palm Springs airport is easier navigate. As our connection was only an approximately 50 minutes, we asked staff for insights for the Chicago airport in terms of transferring into the other terminal from which our flight left, and they were unhelpful. However, the United App was very helpful in terms of notifications and even providing directions. The Chicago to Detroit flight was significantly delayed which we all know does happen. However, there were very few updates or notifications as to why this was happening when we would actually arrive. It took nearly 30 minutes for bags to make it to baggage claim. We arrived nearly 1 hour late on a 40 minute flight.

Flight cancelled due to fog. No other flights available for 36 hours. Directed by United to book passage on another carrier, and submit receipts for reimbursement. Did that. United now states they will not reimburse. Currently out 2 grand.

The flight was delayed by 4 hours !!!!! It was very uncomfortable , and they told us only one our before departure

The CX617 from HK to BKK was delayed more than 1.5 hours.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

The only problem experienced was a ground stop in Chicago due to weather. But the crew handled everything professionally. They prioritized rebooking those passengers who had connecting flights and then deplaning the other passengers. When the hold was lifted, they efficiently re-boarded all the passengers so that we could depart before our departure limit expired.

Our second leg to Jackson WY was unable to land due to weather. We were flown back to Dallas after stopping in SLC. We were given hotel rooms and vouchers. We were told that we would be back on the same plane in the morning. Instead we were given a different flight with different seats. Not a good experience. No one knew what was going on.

Book cheap flights from White Plains to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from White Plains to Chicago found on KAYAK in the last 72 hours.
6/17Mon
2 stops
21h 51mHPN-ORD
$106
6/1Sat
1 stopDelta
4h 28mHPN-MDW
$113
6/11Tue
1 stopDelta
6h 11mHPN-ORD
$113
5/20Mon
2 stops
21h 45mHPN-ORD
$122
5/31Fri
2 stops
21h 45mHPN-ORD
$138
6/11Tue
3 stops
28h 13mHPN-ORD
$140
6/18Tue
1 stopAmerican Airlines
8h 12mHPN-ORD
$245
6/18Tue
nonstopAmerican Airlines
2h 33mHPN-ORD
$278
7/25Thu
1 stopAmerican Airlines
5h 06mHPN-ORD
$286
6/2Sun
nonstopAmerican Airlines
2h 31mHPN-ORD
$307

Search by stops

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Last minute flights from White Plains to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from White Plains to Chicago that are departing in the next 10 days.
5/19Sun
multi-stopAmerican Airlines
5h 15mHPN-ORD
6/9Sun
nonstopAmerican Airlines
2h 18mORD-HPN
$624
5/19Sun
multi-stopDelta
5h 21mHPN-MDW
6/9Sun
multi-stopDelta
5h 03mMDW-HPN
$646
5/16Thu
multi-stopDelta
6h 32mHPN-ORD
5/26Sun
multi-stopDelta
3h 50mORD-HPN
$668
5/16Thu
nonstopAmerican Airlines
2h 31mHPN-ORD
5/26Sun
nonstopAmerican Airlines
2h 08mORD-HPN
$678
5/16Thu
nonstopAmerican Airlines
2h 31mHPN-ORD
5/20Mon
multi-stopAmerican Airlines
6h 23mORD-HPN
$686
5/15Wed
nonstopAmerican Airlines
2h 31mHPN-ORD
5/18Sat
nonstopAmerican Airlines
2h 08mORD-HPN
$689
5/16Thu
multi-stopAmerican Airlines
5h 26mHPN-ORD
5/20Mon
multi-stopAmerican Airlines
5h 48mORD-HPN
$694
5/16Thu
nonstopAmerican Airlines
2h 31mHPN-ORD
5/19Sun
multi-stopAmerican Airlines
4h 40mORD-HPN
$697
5/16Thu
multi-stopAmerican Airlines
7h 40mHPN-ORD
5/19Sun
multi-stopAmerican Airlines
7h 25mORD-HPN
$705
5/17Fri
multi-stop
11h 19mHPN-ORD
5/19Sun
multi-stop
16h 23mORD-HPN
$775

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White Plains - Chicago Flights

Departure:

White Plains (undefined)United States

Return flight deals:

Chicago - White Plains

Cabin classes:

$799
$1,098
$1,078
$283