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Cheap flights from White Plains to Chicago from $93

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 1/21. 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

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Multiple Airlines Logo
1:10 pm - 11:47 am
HPN
-
ORD
23h 37m2 stops
Multiple Airlines Logo
5:35 am - 11:28 am
ORD
-
HPN
4h 53m1 stop
$212Multiple Airlines
Fri, Jan 9 - Mon, Jan 12
American Airlines Logo
12:00 pm - 1:45 pm
HPN
-
ORD
2h 45mnonstop
American Airlines Logo
7:49 pm - 11:00 pm
ORD
-
HPN
2h 11mnonstop
$349American Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
12:09 pm - 7:02 pm
HPN
-
ORD
31h 53m2 stops
Multiple Airlines Logo
5:35 am - 11:28 am
ORD
-
HPN
4h 53m1 stop
$351Multiple Airlines
Tue, Jan 6 - Fri, Jan 9
Multiple Airlines Logo
1:20 pm - 8:31 am
HPN
-
ORD
44h 11m2 stops
Multiple Airlines Logo
5:35 am - 11:28 am
ORD
-
HPN
4h 53m1 stop
$352Multiple Airlines
Mon, Jan 5 - Fri, Jan 9
American Airlines Logo
6:30 am - 10:52 am
HPN
-
ORD
5h 22m1 stop
American Airlines Logo
8:18 am - 11:28 am
ORD
-
HPN
2h 10mnonstop
$359American Airlines
Tue, Jan 20 - Tue, Jan 27
Multiple Airlines Logo
12:08 pm - 10:52 am
HPN
-
ORD
23h 44m2 stops
Multiple Airlines Logo
12:34 pm - 11:28 am
ORD
-
HPN
21h 54m1 stop
$367Multiple Airlines
Mon, Mar 16 - Thu, Mar 19
Delta Logo
12:36 pm - 5:55 pm
HPN
-
MDW
6h 19m1 stop
Delta Logo
9:32 am - 3:49 pm
MDW
-
HPN
5h 17m1 stop
$369Delta
Tue, Jan 20 - Tue, Jan 27
Delta Logo
5:12 pm - 9:05 pm
HPN
-
ORD
4h 53m1 stop
Delta Logo
7:05 am - 2:26 pm
ORD
-
HPN
6h 21m1 stop
$369Delta
Tue, Jan 20 - Tue, Jan 27
American Airlines Logo
6:00 am - 7:52 am
HPN
-
ORD
2h 52mnonstop
American Airlines Logo
12:50 pm - 3:59 pm
ORD
-
HPN
2h 09mnonstop
$380American Airlines
Wed, Feb 25 - Sun, Mar 1
Delta Logo
6:59 pm - 9:56 am
HPN
-
MDW
15h 57m1 stop
Delta Logo
9:30 am - 4:35 pm
MDW
-
HPN
6h 05m1 stop
$382Delta
Mon, Mar 30 - Sat, Apr 4

American Airlines flights from White Plains to Chicago

Our best American Airlines deals on White Plains to Chicago flight tickets
American Airlines
Jan 20
HPN12:00 pmWhite Plains Westchester County
2h 45m
ORD1:45 pmChicago O'Hare Intl
Jan 27
ORD7:49 pmChicago O'Hare Intl
2h 11m
HPN11:00 pmWhite Plains Westchester County
$349
Find similar
American Airlines
Jan 20
HPN6:30 amWhite Plains Westchester County
5h 22m
1 stop
ORD10:52 amChicago O'Hare Intl
Jan 27
ORD8:18 amChicago O'Hare Intl
2h 10m
HPN11:28 amWhite Plains Westchester County
$359
Find similar
American Airlines
Feb 25
HPN6:00 amWhite Plains Westchester County
2h 52m
ORD7:52 amChicago O'Hare Intl
Mar 1
ORD12:50 pmChicago O'Hare Intl
2h 09m
HPN3:59 pmWhite Plains Westchester County
$380
Find similar

Delta flights from White Plains to Chicago

Our best Delta deals on White Plains to Chicago flight tickets
Delta
Jan 20
HPN5:12 pmWhite Plains Westchester County
4h 53m
1 stop
ORD9:05 pmChicago O'Hare Intl
Jan 27
ORD7:05 amChicago O'Hare Intl
6h 21m
1 stop
HPN2:26 pmWhite Plains Westchester County
$369
Find similar
Delta
Mar 30
HPN6:59 pmWhite Plains Westchester County
14h 31m
1 stop
ORD8:30 amChicago O'Hare Intl
Apr 4
ORD9:35 amChicago O'Hare Intl
6h 00m
1 stop
HPN4:35 pmWhite Plains Westchester County
$382
Find similar
Delta
Mar 30
HPN3:13 pmWhite Plains Westchester County
18h 17m
2 stops
ORD8:30 amChicago O'Hare Intl
Apr 4
ORD7:10 amChicago O'Hare Intl
3h 33m
1 stop
HPN11:43 amWhite Plains Westchester County
$387
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago 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 December 22, 2025.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 1/9

1:10 pm-11:47 am

2 stops23h 37m

Chicago O'Hare Intl

Mon 1/12

5:35 am-11:28 am

1 stop4h 53m

$212

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 1/20

12:00 pm-1:45 pm

Nonstop2h 45m

Chicago O'Hare Intl

Tue 1/27

7:49 pm-11:00 pm

Nonstop2h 11m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 1/6

12:09 pm-7:02 pm

2 stops31h 53m

Chicago O'Hare Intl

Fri 1/9

5:35 am-11:28 am

1 stop4h 53m

$351

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 1/5

1:20 pm-8:31 am

2 stops44h 11m

Chicago O'Hare Intl

Fri 1/9

5:35 am-11:28 am

1 stop4h 53m

$352

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 1/20

6:30 am-10:52 am

1 stop5h 22m

Chicago O'Hare Intl

Tue 1/27

8:18 am-11:28 am

Nonstop2h 10m

$359

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 3/16

12:08 pm-10:52 am

2 stops23h 44m

Chicago O'Hare Intl

Thu 3/19

12:34 pm-11:28 am

1 stop21h 54m

$367

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 1/20

12:36 pm-5:55 pm

1 stop6h 19m

Chicago Midway

Tue 1/27

9:32 am-3:49 pm

1 stop5h 17m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 1/20

5:12 pm-9:05 pm

1 stop4h 53m

Chicago O'Hare Intl

Tue 1/27

7:05 am-2:26 pm

1 stop6h 21m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 2/25

6:00 am-7:52 am

Nonstop2h 52m

Chicago O'Hare Intl

Sun 3/1

12:50 pm-3:59 pm

Nonstop2h 09m

$380

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Mon 3/30

6:59 pm-9:56 am

1 stop15h 57m

Chicago Midway

Sat 4/4

9:30 am-4:35 pm

1 stop6h 05m

$382

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

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?

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from White Plains, with most prices found around $450. If you’re not able to fly to Chicago in September, then March is your next best option. Flight prices from White Plains to Chicago during March average around $451.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as $291. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from White Plains to Chicago for around $369.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from White Plains to Chicago during this time can be as low as $269. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $365.

What is the cheapest White Plains Westchester County to Chicago flight route?

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

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

You are more likely to see cheaper flights to Chicago from White Plains when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $467 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from White Plains for as low as $392 on momondo.

What cabin class options are available on White Plains Westchester County to Chicago flights?

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

Can stopping save me money on White Plains to Chicago flights?

You could potentially save up to 19% on your flight if you consider stops on a White Plains to Chicago flight.

How have White Plains to Chicago flight prices changed over time?

As of December 2025, prices for White Plains to Chicago flights are approximately 34% cheaper when compared to flights at the same time last year.

When to book flights from White Plains to Chicago

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

Cheap White Plains to Chicago (HPN to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from White Plains to Chicago

Best Price Found

$278

Fastest flight time

2h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from White Plains in the past 72 hours is $278. The best round-trip flight deal from White Plains to Chicago found on momondo in the last 72 hours is $380.
The fastest flight from White Plains to Chicago takes 2h 40m
Direct flights go from White Plains to Chicago every day.
There are 3 airports in Chicago. From White Plains there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • How far is White Plains Westchester County to Chicago by plane?

    Chicago is 719.0 mi away from White Plains Westchester County. A reasonable flight in good conditions will take 2h 40m.

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

    Prices for flights from White Plains Westchester County Airport to Chicago are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from White Plains Westchester County Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from White Plains to Chicago?

  • What is the most popular airline from White Plains to Chicago?

Best airlines flying from White Plains to Chicago

Compare and see reviews for airlines that fly from White Plains to Chicago with momondo
Airline
Rating
Free Cancellation
Price
American AirlinesPriceFrom $349Free CancellationRating
7.2
11,052 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago

    Across 23 American Airlines flights from White Plains to Chicago this week, the average price was $479, with the best American Airlines deals starting from $349 round-trip. 11,052 users have rated American Airlines on momondo, with an average score of 7.2/10.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from White Plains to Chicago. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo allows you to filter the results for White Plains to Chicago flights to just show those with flexible booking policies.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from White Plains to Chicago.

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

Price alerts on flights to Chicago from White Plains are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport