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Cheap flights from White Plains to Chicago from $129

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from White Plains to Chicago departing on 6/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:08 pm - 11:06 pm
HPN
-
ORD
11h 58m
1 stop
Multiple Airlines Logo
1:59 pm - 11:20 am
ORD
-
HPN
20h 21m
2 stops
$382Multiple Airlines
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
12:00 pm - 2:39 pm
HPN
-
ORD
27h 39m
1 stop
Multiple Airlines Logo
1:59 pm - 11:20 am
ORD
-
HPN
20h 21m
2 stops
$385Multiple Airlines
Sat, May 9 - Fri, May 15
Multiple Airlines Logo
12:00 pm - 2:39 pm
HPN
-
ORD
27h 39m
1 stop
Multiple Airlines Logo
5:49 pm - 5:29 pm
ORD
-
HPN
22h 40m
2 stops
$388Multiple Airlines
Sat, May 16 - Sun, May 17
Multiple Airlines Logo
8:00 am - 2:39 pm
HPN
-
ORD
7h 39m
1 stop
Multiple Airlines Logo
8:05 am - 11:20 am
ORD
-
HPN
50h 15m
2 stops
$389Multiple Airlines
Sun, May 17 - Thu, May 21
Multiple Airlines Logo
8:00 am - 2:39 pm
HPN
-
ORD
7h 39m
1 stop
Multiple Airlines Logo
1:59 pm - 11:20 am
ORD
-
HPN
20h 21m
2 stops
$392Multiple Airlines
Thu, May 14 - Fri, May 15
American Airlines Logo
4:30 pm - 6:21 pm
HPN
-
ORD
2h 51mnonstop
American Airlines Logo
7:36 pm - 10:59 pm
ORD
-
HPN
2h 23mnonstop
$395American Airlines
Sat, Jul 11 - Sat, Jul 25
Multiple Airlines Logo
6:09 pm - 12:23 pm
HPN
-
ORD
19h 14m
2 stops
Multiple Airlines Logo
8:39 am - 8:59 pm
ORD
-
HPN
11h 20m
1 stop
$398Multiple Airlines
Fri, May 15 - Sun, May 17
Multiple Airlines Logo
12:08 pm - 11:06 pm
HPN
-
ORD
11h 58m
1 stop
Multiple Airlines Logo
1:59 pm - 5:29 pm
ORD
-
HPN
26h 30m
2 stops
$400Multiple Airlines
Mon, May 4 - Thu, May 7
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
$404Multiple Airlines
Mon, May 4 - Wed, May 6
American Airlines Logo
7:55 am - 12:17 pm
HPN
-
ORD
5h 22m
1 stop
American Airlines Logo
1:57 pm - 5:15 pm
ORD
-
HPN
2h 18mnonstop
$405American Airlines
Sat, Jul 11 - Sat, Jul 18

American Airlines flights from White Plains to Chicago O'Hare Intl Airport

Our best American Airlines deals on White Plains to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jul 11
HPN4:30 pmWhite Plains Westchester County
2h 51m
ORD6:21 pmChicago O'Hare Intl
Jul 25
ORD7:36 pmChicago O'Hare Intl
2h 23m
HPN10:59 pmWhite Plains Westchester County
$395
American Airlines
Jul 11
HPN7:55 amWhite Plains Westchester County
5h 22m
1 stop
ORD12:17 pmChicago O'Hare Intl
Jul 18
ORD1:57 pmChicago O'Hare Intl
2h 18m
HPN5:15 pmWhite Plains Westchester County
$405
American Airlines
May 29
HPN6:30 pmWhite Plains Westchester County
2h 56m
ORD8:26 pmChicago O'Hare Intl
Jun 1
ORD8:10 amChicago O'Hare Intl
2h 19m
HPN11:29 amWhite Plains Westchester County
$429

Delta flights from White Plains to Chicago O'Hare Intl Airport

Our best Delta deals on White Plains to Chicago O'Hare Intl Airport flight tickets
Delta
Jul 11
HPN12:35 pmWhite Plains Westchester County
4h 48m
1 stop
ORD4:23 pmChicago O'Hare Intl
Jul 25
ORD5:15 amChicago O'Hare Intl
8h 14m
1 stop
HPN2:29 pmWhite Plains Westchester County
$415
Delta
May 9
HPN6:00 amWhite Plains Westchester County
13h 41m
1 stop
ORD6:41 pmChicago O'Hare Intl
May 16
ORD5:30 amChicago O'Hare Intl
15h 50m
1 stop
HPN10:20 pmWhite Plains Westchester County
$447
Delta
May 29
HPN12:50 pmWhite Plains Westchester County
6h 45m
1 stop
ORD6:35 pmChicago O'Hare Intl
Jun 1
ORD5:30 amChicago O'Hare Intl
7h 59m
1 stop
HPN2:29 pmWhite Plains Westchester County
$449

momondo Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago O'Hare Intl Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 20, 2026.
Use the filters below to find and compare flights from White Plains to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 5/4

12:08 pm-11:06 pm

1 stop11h 58m

Chicago O'Hare Intl

Fri 5/8

1:59 pm-11:20 am

2 stops20h 21m

$382

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/9

12:00 pm-2:39 pm

1 stop27h 39m

Chicago O'Hare Intl

Fri 5/15

1:59 pm-11:20 am

2 stops20h 21m

$385

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 5/16

12:00 pm-2:39 pm

1 stop27h 39m

Chicago O'Hare Intl

Sun 5/17

5:49 pm-5:29 pm

2 stops22h 40m

$388

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sun 5/17

8:00 am-2:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Thu 5/21

8:05 am-11:20 am

2 stops50h 15m

$389

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 5/14

8:00 am-2:39 pm

1 stop7h 39m

Chicago O'Hare Intl

Fri 5/15

1:59 pm-11:20 am

2 stops20h 21m

$392
Quickest round-trip

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 7/11

4:30 pm-6:21 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sat 7/25

7:36 pm-10:59 pm

Nonstop2h 23m

$395

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 5/15

6:09 pm-12:23 pm

2 stops19h 14m

Chicago O'Hare Intl

Sun 5/17

8:39 am-8:59 pm

1 stop11h 20m

$398

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 5/4

12:08 pm-11:06 pm

1 stop11h 58m

Chicago O'Hare Intl

Thu 5/7

1:59 pm-5:29 pm

2 stops26h 30m

$400

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 5/4

12:08 pm-11:06 pm

1 stop11h 58m

Chicago O'Hare Intl

Wed 5/6

1:59 pm-8:59 pm

2 stops30h 00m

$404

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 7/11

7:55 am-12:17 pm

1 stop5h 22m

Chicago O'Hare Intl

Sat 7/18

1:57 pm-5:15 pm

Nonstop2h 18m

$405

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from White Plains to Chicago O'Hare Intl Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between White Plains and Chicago O'Hare Intl Airport?

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from White Plains averaging around $449.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $288. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from White Plains because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $366.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from White Plains in the evening is the least expensive time of day to depart. momondo users have found prices as low as $275 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $362. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest White Plains Westchester County to Chicago O'Hare Intl flight route?

Fly from White Plains Westchester County to Chicago O'Hare Intl for the best White Plains Westchester County - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from White Plains when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $480 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from White Plains for as low as $394 on momondo.

What cabin class options are available on White Plains Westchester County to Chicago O'Hare Intl flights?

There are 3 cabin classes available to choose from on White Plains Westchester County to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have White Plains to Chicago O'Hare Intl Airport flight prices changed over time?

As of April 2026, prices for White Plains to Chicago O'Hare Intl Airport flights are approximately 219% more expensive when compared to flights at the same time last year.

When to book flights from White Plains to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from White Plains to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap White Plains to Chicago O'Hare Intl Airport (HPN to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from White Plains to Chicago O'Hare Intl Airport

Best Price Found

$265

Fastest flight time

2h 43m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from White Plains in the past 72 hours is $265. The best round-trip flight deal from White Plains to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $457.
The fastest flight from White Plains to Chicago O'Hare Intl Airport takes 2h 43m
Direct flights go from White Plains to Chicago O'Hare Intl Airport every day.
Search flight deals

Frequently asked questions about flying from White Plains to Chicago O'Hare Intl Airport

  • How far is White Plains Westchester County to Chicago O'Hare Intl by plane?

    The distance between White Plains Westchester County and Chicago O'Hare Intl is about 733.3 mi. By plane, this route typically takes 2h 43m.

  • When did momondo last update prices for flights from White Plains Westchester County Airport to Chicago O'Hare Intl Airport?

    Prices for flights from White Plains Westchester County Airport to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from White Plains Westchester County Airport to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from White Plains Westchester County Airport to Chicago O'Hare Intl Airport?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from White Plains Westchester County Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

  • What is the most popular plane model from White Plains to Chicago O'Hare Intl Airport?

  • What is the most popular airline from White Plains to Chicago O'Hare Intl Airport?

Best airlines flying from White Plains to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from White Plains to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $375Free CancellationRating
7.1
11,629 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago O'Hare Intl Airport

    American Airlines flight deals from White Plains to Chicago O'Hare Intl Airport start from $375 round-trip. Over the 26 American Airlines flights for this route in a normal week, average airfare is usually $493 round-trip - but some users have found much cheaper deals with momondo.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
South Haven
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Janesville
Racine
Hammond
Elgin
Tinley Park
Evanston

Why use momondo?

Why should I use momondo to find a flight deal from White Plains to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from White Plains to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from White Plains to Chicago with flexible booking policies on momondo?

All flight searches from White Plains to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from White Plains to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from White Plains.

I’m not ready to book a flight from White Plains to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from White Plains and alert you when they change.

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