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Cheap flights from White Plains to Chicago from $124

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 12/10. 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

American Airlines Logo
6:00 am - 7:36 amHPN-ORD
2h 36mnonstop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$349American Airlines
Find Deal
Wed, Oct 15 - Wed, Oct 22
Multiple Airlines Logo
8:25 am - 10:17 amHPN-ORD
26h 52m2 stops
Multiple Airlines Logo
11:36 am - 11:28 amORD-HPN
22h 52m1 stop
$352Multiple Airlines
Find Deal
Fri, Oct 3 - Sun, Oct 5
American Airlines Logo
6:30 am - 12:03 pmHPN-ORD
6h 33m1 stop
American Airlines Logo
8:17 am - 11:29 amORD-HPN
2h 12mnonstop
$359American Airlines
Find Deal
Tue, Oct 21 - Sat, Oct 25
Multiple Airlines Logo
8:25 am - 10:18 amHPN-ORD
26h 53m2 stops
Multiple Airlines Logo
11:36 am - 11:28 amORD-HPN
22h 52m1 stop
$364Multiple Airlines
Find Deal
Mon, Sep 29 - Thu, Oct 2
Multiple Airlines Logo
8:00 am - 11:28 pmHPN-ORD
16h 28m2 stops
Multiple Airlines Logo
1:50 pm - 11:28 amORD-HPN
20h 38m1 stop
$367Multiple Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
12:55 pm - 6:25 pmHPN-MDW
6h 30m1 stop
Delta Logo
11:10 am - 3:49 pmMDW-HPN
3h 39m1 stop
$369Delta
Find Deal
Tue, Oct 21 - Sat, Oct 25
Delta Logo
5:20 pm - 8:23 pmHPN-ORD
4h 03m1 stop
Delta Logo
5:20 am - 12:00 pmORD-HPN
5h 40m1 stop
$369Delta
Find Deal
Tue, Oct 21 - Sat, Oct 25
American Airlines Logo
12:00 pm - 1:35 pmHPN-ORD
2h 35mnonstop
American Airlines Logo
6:29 pm - 9:59 pmORD-HPN
2h 30mnonstop
$380American Airlines
Find Deal
Sat, Oct 25 - Mon, Oct 27
Multiple Airlines Logo
8:00 am - 11:39 pmHPN-ORD
16h 39m2 stops
Multiple Airlines Logo
11:36 am - 11:28 amORD-HPN
22h 52m1 stop
$381Multiple Airlines
Find Deal
Thu, Oct 2 - Sun, Oct 5
Delta Logo
4:29 pm - 10:14 pmHPN-MDW
6h 45m1 stop
Delta Logo
9:35 am - 3:49 pmMDW-HPN
5h 14m1 stop
$400Delta
Find Deal
Sat, Oct 25 - Mon, Oct 27

American Airlines flights from White Plains to Chicago

Our best American Airlines deals on White Plains to Chicago flight tickets
American Airlines
Oct 15
HPN6:00 amWhite Plains Westchester County
2h 36m
ORD7:36 amChicago O'Hare Intl
Oct 22
ORD12:49 pmChicago O'Hare Intl
2h 10m
HPN3:59 pmWhite Plains Westchester County
$349
Find similar
American Airlines
Oct 21
HPN6:30 amWhite Plains Westchester County
6h 33m
1 stop
ORD12:03 pmChicago O'Hare Intl
Oct 25
ORD8:17 amChicago O'Hare Intl
2h 12m
HPN11:29 amWhite Plains Westchester County
$359
Find similar
American Airlines
Oct 25
HPN12:00 pmWhite Plains Westchester County
2h 35m
ORD1:35 pmChicago O'Hare Intl
Oct 27
ORD6:29 pmChicago O'Hare Intl
2h 30m
HPN9:59 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
Oct 21
HPN5:20 pmWhite Plains Westchester County
4h 03m
1 stop
ORD8:23 pmChicago O'Hare Intl
Oct 25
ORD5:20 amChicago O'Hare Intl
5h 40m
1 stop
HPN12:00 pmWhite Plains Westchester County
$369
Find similar
Delta
Oct 25
HPN6:40 pmWhite Plains Westchester County
6h 18m
1 stop
ORD11:58 pmChicago O'Hare Intl
Nov 17
ORD6:45 amChicago O'Hare Intl
4h 22m
1 stop
HPN12:07 pmWhite Plains Westchester County
$400
Find similar
Delta
Oct 11
HPN3:15 pmWhite Plains Westchester County
7h 04m
1 stop
ORD9:19 pmChicago O'Hare Intl
Oct 14
ORD7:10 amChicago O'Hare Intl
3h 49m
1 stop
HPN11:59 amWhite Plains Westchester County
$404
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 September 16, 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

Wed 10/15

6:00 am-7:36 am

Nonstop2h 36m

Chicago O'Hare Intl

Wed 10/22

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Fri 10/3

8:25 am-10:17 am

2 stops26h 52m

Chicago O'Hare Intl

Sun 10/5

11:36 am-11:28 am

1 stop22h 52m

$352

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 10/21

6:30 am-12:03 pm

1 stop6h 33m

Chicago O'Hare Intl

Sat 10/25

8:17 am-11:29 am

Nonstop2h 12m

$359

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Mon 9/29

8:25 am-10:18 am

2 stops26h 53m

Chicago O'Hare Intl

Thu 10/2

11:36 am-11:28 am

1 stop22h 52m

$364

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 10/30

8:00 am-11:28 pm

2 stops16h 28m

Chicago O'Hare Intl

Sun 11/2

1:50 pm-11:28 am

1 stop20h 38m

$367

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 10/21

12:55 pm-6:25 pm

1 stop6h 30m

Chicago Midway

Sat 10/25

11:10 am-3:49 pm

1 stop3h 39m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Tue 10/21

5:20 pm-8:23 pm

1 stop4h 03m

Chicago O'Hare Intl

Sat 10/25

5:20 am-12:00 pm

1 stop5h 40m

$369

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/25

12:00 pm-1:35 pm

Nonstop2h 35m

Chicago O'Hare Intl

Mon 10/27

6:29 pm-9:59 pm

Nonstop2h 30m

$380

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 10/2

8:00 am-11:39 pm

2 stops16h 39m

Chicago O'Hare Intl

Sun 10/5

11:36 am-11:28 am

1 stop22h 52m

$381

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 10/25

4:29 pm-10:14 pm

1 stop6h 45m

Chicago Midway

Mon 10/27

9:35 am-3:49 pm

1 stop5h 14m

$400

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 $406. If you’re not able to fly to Chicago in September, then November is your next best option. Flight prices from White Plains to Chicago during November average around $434.

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 $295. 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 $389.

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 $261. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $368.

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 $463 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 $348 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 7% 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 September 2025, prices for White Plains to Chicago flights are approximately 59% 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

$278

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Chicago

1 airport
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 $387.
The fastest flight from White Plains to Chicago takes 2h 30m
Direct flights go from White Plains to Chicago every day.
There is 1 airport near Chicago: 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 30m.

  • 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
United AirlinesPriceFrom $96Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
American AirlinesPriceFrom $349Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago

    Across 26 American Airlines flights from White Plains to Chicago this week, the average price was $470, with the best American Airlines deals starting from $349 round-trip. 10,000 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
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