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Cheap flights from White Plains to Chicago from $109

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 3/3. 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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Find the cheapest flights from White Plains to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
3:15 pm - 9:30 pm
HPN
-
ORD
7h 15m
1 stop
Delta Logo
8:55 am - 4:37 pm
ORD
-
HPN
6h 42m
1 stop
$277Delta
mer., févr. 25 - mer., mars 18
Multiple Airlines Logo
12:08 pm - 5:16 pm
HPN
-
ORD
6h 08m
1 stop
Multiple Airlines Logo
6:31 am - 12:47 pm
ORD
-
HPN
29h 16m
2 stops
$283Multiple Airlines
ven., avr. 10 - mar., avr. 14
Multiple Airlines Logo
12:08 pm - 11:37 pm
HPN
-
ORD
12h 29m
1 stop
Multiple Airlines Logo
11:55 am - 11:28 am
ORD
-
HPN
22h 33m
2 stops
$294Multiple Airlines
ven., févr. 27 - jeu., mars 5
American Airlines Logo
4:30 pm - 6:18 pm
HPN
-
ORD
2h 48mnonstop
American Airlines Logo
8:59 pm - 10:58 am
ORD
-
HPN
12h 59m
2 stops
$299American Airlines
sam., févr. 21 - sam., févr. 21
Multiple Airlines Logo
1:27 pm - 12:22 am
HPN
-
ORD
11h 55m
2 stops
Multiple Airlines Logo
12:34 pm - 11:28 am
ORD
-
HPN
21h 54m
1 stop
$302Multiple Airlines
mer., mars 18 - jeu., mars 19
Multiple Airlines Logo
12:08 pm - 11:16 pm
HPN
-
ORD
12h 08m
1 stop
Multiple Airlines Logo
3:52 pm - 5:29 pm
ORD
-
HPN
24h 37m
2 stops
$307Multiple Airlines
lun., mai 4 - jeu., mai 7
Multiple Airlines Logo
8:00 am - 10:52 am
HPN
-
ORD
27h 52m
2 stops
Multiple Airlines Logo
12:34 pm - 11:28 am
ORD
-
HPN
21h 54m
1 stop
$309Multiple Airlines
dim., mars 15 - jeu., mars 19
Multiple Airlines Logo
12:08 pm - 6:30 pm
HPN
-
ORD
7h 22m
1 stop
Multiple Airlines Logo
4:28 pm - 12:47 pm
ORD
-
HPN
19h 19m
2 stops
$311Multiple Airlines
lun., avr. 13 - mar., avr. 14
Delta Logo
12:36 pm - 5:37 pm
HPN
-
MDW
6h 01m
1 stop
Delta Logo
10:45 am - 6:18 pm
MDW
-
HPN
6h 33m
1 stop
$375Delta
mer., mars 4 - mer., mars 11
Delta Logo
12:35 pm - 5:54 pm
HPN
-
MDW
6h 19m
1 stop
Delta Logo
9:30 am - 4:35 pm
MDW
-
HPN
6h 05m
1 stop
$405Delta
mer., avr. 1 - sam., avr. 11

American Airlines flights from White Plains to Chicago

Our best American Airlines deals on White Plains to Chicago flight tickets
American Airlines
Feb 21
HPN4:30 pmWhite Plains Westchester County
2h 48m
ORD6:18 pmChicago O'Hare Intl
Feb 21
ORD8:59 pmChicago O'Hare Intl
12h 59m
2 stops
HPN10:58 amWhite Plains Westchester County
$299
American Airlines
Mar 11
HPN6:30 amWhite Plains Westchester County
2h 50m
ORD8:20 amChicago O'Hare Intl
Mar 14
ORD6:38 pmChicago O'Hare Intl
2h 21m
HPN9:59 pmWhite Plains Westchester County
$355
American Airlines
Mar 18
HPN5:29 pmWhite Plains Westchester County
2h 48m
ORD7:17 pmChicago O'Hare Intl
Apr 1
ORD6:38 pmChicago O'Hare Intl
2h 21m
HPN9:59 pmWhite Plains Westchester County
$363

Delta flights from White Plains to Chicago

Our best Delta deals on White Plains to Chicago flight tickets
Delta
Feb 25
HPN3:15 pmWhite Plains Westchester County
7h 15m
1 stop
ORD9:30 pmChicago O'Hare Intl
Mar 18
ORD8:55 amChicago O'Hare Intl
6h 42m
1 stop
HPN4:37 pmWhite Plains Westchester County
$277
Delta
Mar 11
HPN4:29 pmWhite Plains Westchester County
8h 25m
1 stop
ORD11:54 pmChicago O'Hare Intl
Mar 31
ORD5:30 amChicago O'Hare Intl
5h 33m
1 stop
HPN12:03 pmWhite Plains Westchester County
$375
Delta
Feb 25
HPN12:36 pmWhite Plains Westchester County
5h 05m
1 stop
ORD4:41 pmChicago O'Hare Intl
Mar 18
ORD5:30 amChicago O'Hare Intl
5h 33m
1 stop
HPN12:03 pmWhite Plains Westchester County
$405

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 février 5, 2026.
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

mer. 2/25

3:15 pm-9:30 pm

1 stop7h 15m

Chicago O'Hare Intl

mer. 3/18

8:55 am-4:37 pm

1 stop6h 42m

$277

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

ven. 4/10

12:08 pm-5:16 pm

1 stop6h 08m

Chicago O'Hare Intl

mar. 4/14

6:31 am-12:47 pm

2 stops29h 16m

$283

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

ven. 2/27

12:08 pm-11:37 pm

1 stop12h 29m

Chicago O'Hare Intl

jeu. 3/5

11:55 am-11:28 am

2 stops22h 33m

$294

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

sam. 2/21

4:30 pm-6:18 pm

Nonstop2h 48m

Chicago O'Hare Intl

sam. 2/21

8:59 pm-10:58 am

2 stops12h 59m

$299

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

mer. 3/18

1:27 pm-12:22 am

2 stops11h 55m

Chicago O'Hare Intl

jeu. 3/19

12:34 pm-11:28 am

1 stop21h 54m

$302

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 5/4

12:08 pm-11:16 pm

1 stop12h 08m

Chicago O'Hare Intl

jeu. 5/7

3:52 pm-5:29 pm

2 stops24h 37m

$307

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

dim. 3/15

8:00 am-10:52 am

2 stops27h 52m

Chicago O'Hare Intl

jeu. 3/19

12:34 pm-11:28 am

1 stop21h 54m

$309

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

lun. 4/13

12:08 pm-6:30 pm

1 stop7h 22m

Chicago O'Hare Intl

mar. 4/14

4:28 pm-12:47 pm

2 stops19h 19m

$311

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

mer. 3/4

12:36 pm-5:37 pm

1 stop6h 01m

Chicago Midway

mer. 3/11

10:45 am-6:18 pm

1 stop6h 33m

$375

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

mer. 4/1

12:35 pm-5:54 pm

1 stop6h 19m

Chicago Midway

sam. 4/11

9:30 am-4:35 pm

1 stop6h 05m

$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

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 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 $289. 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 $362.

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 $267. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $362.

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 $471 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 $412 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 40% 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 February 2026, prices for White Plains to Chicago flights are approximately 230% more expensive 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

$280

Fastest flight time

2h 38m

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 $280. The best round-trip flight deal from White Plains to Chicago found on momondo in the last 72 hours is $336.
The fastest flight from White Plains to Chicago takes 2h 38m
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 38m.

  • 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 $374Free CancellationRating
7.2
11,237 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago

    Across 19 American Airlines flights from White Plains to Chicago this week, the average price was $481, with the best American Airlines deals starting from $374 round-trip. 11,237 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
Schererville
Valparaiso
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