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Cheap flights from White Plains to Chicago from $202

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 9/30. 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

Delta Logo
12:42 pm - 8:20 pmHPN-ORD
8h 38m1 stop
Delta Logo
8:55 am - 12:04 pmORD-HPN
26h 09m1 stop
$297Delta
Find Deal
Wed, Oct 1 - Tue, Oct 7
Delta Logo
12:42 pm - 8:20 pmHPN-ORD
8h 38m1 stop
Delta Logo
8:55 am - 12:04 pmORD-HPN
26h 09m1 stop
$300Delta
Find Deal
Wed, Oct 1 - Mon, Oct 6
Delta Logo
12:42 pm - 9:34 pmHPN-ORD
9h 52m1 stop
Delta Logo
8:55 am - 12:04 pmORD-HPN
26h 09m1 stop
$307Delta
Find Deal
Sat, Oct 4 - Tue, Oct 7
Delta Logo
12:42 pm - 9:34 pmHPN-ORD
9h 52m1 stop
Delta Logo
8:55 am - 12:04 pmORD-HPN
26h 09m1 stop
$310Delta
Find Deal
Sat, Oct 4 - Mon, Oct 6
Delta Logo
12:42 pm - 8:20 pmHPN-ORD
8h 38m1 stop
Delta Logo
7:10 am - 12:04 pmORD-HPN
3h 54m1 stop
$333Delta
Find Deal
Wed, Oct 1 - Wed, Oct 8
American Airlines Logo
11:00 am - 9:10 amHPN-ORD
23h 10m2 stops
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$337American Airlines
Find Deal
Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
6:00 am - 7:36 amHPN-ORD
2h 36mnonstop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$348American Airlines
Find Deal
Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
4:30 pm - 6:10 pmHPN-ORD
2h 40mnonstop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$349American Airlines
Find Deal
Sat, Aug 30 - Sun, Aug 31
American Airlines Logo
1:35 pm - 5:32 pmHPN-ORD
4h 57m1 stop
American Airlines Logo
12:49 pm - 3:59 pmORD-HPN
2h 10mnonstop
$358American Airlines
Find Deal
Sat, Aug 30 - Sun, Aug 31
Logo
8:10 am - 3:43 pmHPN-ORD
8h 33m1 stop
Logo
5:16 pm - 11:29 amORD-HPN
17h 13m2 stops
$396
Find Deal
Thu, Aug 28 - Wed, Sep 3

American Airlines flights from White Plains to Chicago

Our best American Airlines deals on White Plains to Chicago flight tickets
American Airlines
Aug 30
HPN11:00 amWhite Plains Westchester County
23h 10m
2 stops
ORD9:10 amChicago O'Hare Intl
Aug 31
ORD12:49 pmChicago O'Hare Intl
2h 10m
HPN3:59 pmWhite Plains Westchester County
$337
Find similar
American Airlines
Aug 30
HPN6:00 amWhite Plains Westchester County
2h 36m
ORD7:36 amChicago O'Hare Intl
Aug 31
ORD12:49 pmChicago O'Hare Intl
2h 10m
HPN3:59 pmWhite Plains Westchester County
$348
Find similar
American Airlines
Aug 30
HPN4:30 pmWhite Plains Westchester County
2h 40m
ORD6:10 pmChicago O'Hare Intl
Aug 31
ORD12:49 pmChicago O'Hare Intl
2h 10m
HPN3:59 pmWhite Plains Westchester County
$349
Find similar

Delta flights from White Plains to Chicago

Our best Delta deals on White Plains to Chicago flight tickets
Delta
Oct 1
HPN12:42 pmWhite Plains Westchester County
8h 38m
1 stop
ORD8:20 pmChicago O'Hare Intl
Oct 7
ORD8:55 amChicago O'Hare Intl
26h 09m
1 stop
HPN12:04 pmWhite Plains Westchester County
$297
Find similar
Delta
Oct 1
HPN12:42 pmWhite Plains Westchester County
8h 38m
1 stop
ORD8:20 pmChicago O'Hare Intl
Oct 6
ORD8:55 amChicago O'Hare Intl
26h 09m
1 stop
HPN12:04 pmWhite Plains Westchester County
$300
Find similar
Delta
Oct 4
HPN12:42 pmWhite Plains Westchester County
9h 52m
1 stop
ORD9:34 pmChicago O'Hare Intl
Oct 7
ORD8:55 amChicago O'Hare Intl
26h 09m
1 stop
HPN12:04 pmWhite Plains Westchester County
$307
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 August 2, 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 10/1

12:42 pm-8:20 pm

1 stop8h 38m

Chicago O'Hare Intl

Tue 10/7

8:55 am-12:04 pm

1 stop26h 09m

$297

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 10/1

12:42 pm-8:20 pm

1 stop8h 38m

Chicago O'Hare Intl

Mon 10/6

8:55 am-12:04 pm

1 stop26h 09m

$300

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/4

12:42 pm-9:34 pm

1 stop9h 52m

Chicago O'Hare Intl

Tue 10/7

8:55 am-12:04 pm

1 stop26h 09m

$307

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 10/4

12:42 pm-9:34 pm

1 stop9h 52m

Chicago O'Hare Intl

Mon 10/6

8:55 am-12:04 pm

1 stop26h 09m

$310

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Wed 10/1

12:42 pm-8:20 pm

1 stop8h 38m

Chicago O'Hare Intl

Wed 10/8

7:10 am-12:04 pm

1 stop3h 54m

$333

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/30

11:00 am-9:10 am

2 stops23h 10m

Chicago O'Hare Intl

Sun 8/31

12:49 pm-3:59 pm

Nonstop2h 10m

$337

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/30

6:00 am-7:36 am

Nonstop2h 36m

Chicago O'Hare Intl

Sun 8/31

12:49 pm-3:59 pm

Nonstop2h 10m

$348

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/30

4:30 pm-6:10 pm

Nonstop2h 40m

Chicago O'Hare Intl

Sun 8/31

12:49 pm-3:59 pm

Nonstop2h 10m

$349

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Sat 8/30

1:35 pm-5:32 pm

1 stop4h 57m

Chicago O'Hare Intl

Sun 8/31

12:49 pm-3:59 pm

Nonstop2h 10m

$358

White PlainsChicago

HPN - ORD

HPNORD

White Plains Westchester County

Thu 8/28

8:10 am-3:43 pm

1 stop8h 33m

Chicago O'Hare Intl

Wed 9/3

5:16 pm-11:29 am

2 stops17h 13m

$396

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 July is, on average, the cheapest month to fly to Chicago from White Plains, with most prices found around $419. If you’re not able to fly to Chicago in July, then September is your next best option. Flight prices from White Plains to Chicago during September average around $423.

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 $293. 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 $378.

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 $248. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $352.

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 $453 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 $379 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 August 2025, prices for White Plains to Chicago flights are approximately 113% 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

$202

Fastest flight time

2h 29m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from White Plains in the past 72 hours is $202. The best round-trip flight deal from White Plains to Chicago found on momondo in the last 72 hours is $297.
The fastest flight from White Plains to Chicago takes 2h 29m
Direct flights go from White Plains to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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 29m.

  • 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
8,904 reviews
Search United Airlines flights
American AirlinesPriceFrom $334Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • American Airlines Flights From White Plains to Chicago

    Across 20 American Airlines flights from White Plains to Chicago this week, the average price was $459, with the best American Airlines deals starting from $334 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
Portage
Lansing
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