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Cheap flights from White Plains to Chicago from $108

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 5/15. 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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Find the cheapest flights from White Plains to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:29 pm - 10:28 pm
HPN
-
MDW
6h 59m
1 stop
Delta Logo
9:29 am - 4:40 pm
MDW
-
HPN
6h 11m
1 stop
$375Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
12:48 pm - 10:28 pm
HPN
-
MDW
10h 40m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
HPN
5h 00m
1 stop
$391Delta
Thu, Apr 23 - Wed, Apr 29
Delta Logo
6:00 am - 4:26 pm
HPN
-
MDW
11h 26m
1 stop
Delta Logo
9:46 am - 4:40 pm
MDW
-
HPN
5h 54m
1 stop
$397Delta
Fri, Apr 24 - Sat, Apr 25
Delta Logo
12:48 pm - 5:22 pm
HPN
-
MDW
5h 34m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
$405Delta
Wed, Mar 18 - Wed, Apr 15
Delta Logo
6:57 pm - 9:56 am
HPN
-
MDW
15h 59m
1 stop
Delta Logo
5:21 pm - 12:00 pm
MDW
-
HPN
17h 39m
1 stop
$407Delta
Fri, Apr 24 - Mon, Apr 27
Delta Logo
5:20 pm - 10:28 pm
HPN
-
MDW
6h 08m
1 stop
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
$409Delta
Sat, Apr 18 - Mon, Apr 20
Delta Logo
12:30 pm - 8:47 am
HPN
-
MDW
21h 17m
1 stop
Delta Logo
6:38 pm - 11:49 am
MDW
-
HPN
16h 11m
1 stop
$421Delta
Thu, Apr 16 - Mon, Apr 20
Delta Logo
12:48 pm - 10:28 pm
HPN
-
MDW
10h 40m
1 stop
Delta Logo
6:00 am - 12:00 pm
MDW
-
HPN
5h 00m
1 stop
$425Delta
Thu, Apr 23 - Sun, Apr 26
Delta Logo
12:48 pm - 5:22 pm
HPN
-
MDW
5h 34m
1 stop
Delta Logo
9:35 am - 3:49 pm
MDW
-
HPN
5h 14m
1 stop
$439Delta
Tue, Mar 24 - Mon, Mar 30
Delta Logo
4:29 pm - 10:28 pm
HPN
-
MDW
6h 59m
1 stop
Delta Logo
9:27 am - 3:49 pm
MDW
-
HPN
5h 22m
1 stop
$443Delta
Fri, Apr 17 - Sun, Apr 19

Delta flights from White Plains to Chicago Midway Airport

Our best Delta deals on White Plains to Chicago Midway Airport flight tickets
Delta
Apr 21
HPN4:29 pmWhite Plains Westchester County
6h 59m
1 stop
MDW10:28 pmChicago Midway
Apr 25
MDW6:00 amChicago Midway
5h 00m
1 stop
HPN12:00 pmWhite Plains Westchester County
$375
Delta
Apr 23
HPN12:48 pmWhite Plains Westchester County
10h 40m
1 stop
MDW10:28 pmChicago Midway
Apr 29
MDW6:00 amChicago Midway
5h 00m
1 stop
HPN12:00 pmWhite Plains Westchester County
$391
Delta
Apr 24
HPN6:00 amWhite Plains Westchester County
11h 26m
1 stop
MDW4:26 pmChicago Midway
Apr 25
MDW9:46 amChicago Midway
5h 54m
1 stop
HPN4:40 pmWhite Plains Westchester County
$397

momondo Fare Finder

 
Customize your flight search to find flights from White Plains to Chicago Midway 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 February 26, 2026.
Use the filters below to find and compare flights from White Plains to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 4/21

4:29 pm-10:28 pm

1 stop6h 59m

Chicago Midway

Tue 4/28

9:29 am-4:40 pm

1 stop6h 11m

$375

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 4/23

12:48 pm-10:28 pm

1 stop10h 40m

Chicago Midway

Wed 4/29

6:00 am-12:00 pm

1 stop5h 00m

$391

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 4/24

6:00 am-4:26 pm

1 stop11h 26m

Chicago Midway

Sat 4/25

9:46 am-4:40 pm

1 stop5h 54m

$397

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Wed 3/18

12:48 pm-5:22 pm

1 stop5h 34m

Chicago Midway

Wed 4/15

6:00 am-2:29 pm

1 stop7h 29m

$405

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 4/24

6:57 pm-9:56 am

1 stop15h 59m

Chicago Midway

Mon 4/27

5:21 pm-12:00 pm

1 stop17h 39m

$407

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Sat 4/18

5:20 pm-10:28 pm

1 stop6h 08m

Chicago Midway

Mon 4/20

6:00 am-2:29 pm

1 stop7h 29m

$409

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 4/16

12:30 pm-8:47 am

1 stop21h 17m

Chicago Midway

Mon 4/20

6:38 pm-11:49 am

1 stop16h 11m

$421

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Thu 4/23

12:48 pm-10:28 pm

1 stop10h 40m

Chicago Midway

Sun 4/26

6:00 am-12:00 pm

1 stop5h 00m

$425

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Tue 3/24

12:48 pm-5:22 pm

1 stop5h 34m

Chicago Midway

Mon 3/30

9:35 am-3:49 pm

1 stop5h 14m

$439

White PlainsChicago

HPN - MDW

HPNMDW

White Plains Westchester County

Fri 4/17

4:29 pm-10:28 pm

1 stop6h 59m

Chicago Midway

Sun 4/19

9:27 am-3:49 pm

1 stop5h 22m

$443

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from White Plains to Chicago Midway 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 cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Tuesday is the cheapest day to fly to Chicago Midway Airport from White Plains. The lowest ticket price found for a Tuesday departure recently was $254. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday 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 $401.

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

Flying to Chicago Midway Airport from White Plains in the evening is the least expensive time of day to depart. momondo users have found prices as low as $227 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $357. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from White Plains to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from White Plains to Chicago Midway 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 Midway Airport (HPN to MDW) flight deals and tips

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

Fastest flight time

5h 54m

Direct flights

None
The fastest flight from White Plains to Chicago Midway Airport takes 5h 54m
There are no direct flights from White Plains to Chicago Midway Airport. There are no popular flight routes from White Plains to Chicago Midway Airport.
Search flight deals

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

    There are 725.1 mi between White Plains Westchester County and Chicago Midway. Flights usually cover this in 5h 54m, depending on flying conditions and air traffic around both airports.

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

    Prices for flights from White Plains Westchester County Airport to Chicago Midway Airport are refreshed on a daily basis.

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, 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 Midway Airport.

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

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from White Plains to Chicago for you.

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

Flights from White Plains to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for White Plains to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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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