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Cheap flights from Chicago Midway Airport to New York from $144

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to New York departing on 8/18. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:24 am - 3:48 pm
MDW
-
HPN
5h 24m
1 stop
Delta Logo
6:00 am - 11:51 am
HPN
-
MDW
6h 51m
1 stop
$395Delta
Fri, Aug 21 - Mon, Aug 24
Delta Logo
6:00 am - 2:29 pm
MDW
-
HPN
7h 29m
1 stop
Delta Logo
6:00 am - 9:59 am
HPN
-
MDW
4h 59m
1 stop
$415Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
9:19 am - 3:47 pm
MDW
-
HPN
5h 28m
1 stop
Delta Logo
12:36 pm - 6:07 pm
HPN
-
MDW
6h 31m
1 stop
$445Delta
Sat, Jul 25 - Sat, Aug 1
Delta Logo
9:29 am - 3:45 pm
MDW
-
HPN
5h 16m
1 stop
Delta Logo
6:00 am - 11:55 am
HPN
-
MDW
6h 55m
1 stop
$459Delta
Fri, Sep 18 - Tue, Sep 22
Delta Logo
9:19 am - 3:47 pm
MDW
-
HPN
5h 28m
1 stop
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
$475Delta
Sat, Jul 18 - Tue, Jul 21
Delta Logo
11:05 am - 6:07 pm
MDW
-
HPN
6h 02m
1 stop
Delta Logo
4:29 pm - 10:15 pm
HPN
-
MDW
6h 46m
1 stop
$489Delta
Tue, Jul 21 - Mon, Jul 27
Delta Logo
9:24 am - 3:48 pm
MDW
-
HPN
5h 24m
1 stop
Delta Logo
6:00 am - 10:10 am
HPN
-
MDW
5h 10m
1 stop
$503Delta
Fri, Sep 4 - Sun, Sep 6
Delta Logo
9:19 am - 3:47 pm
MDW
-
HPN
5h 28m
1 stop
Delta Logo
10:29 am - 4:15 pm
HPN
-
MDW
6h 46m
1 stop
$519Delta
Thu, Jul 9 - Wed, Jul 15
Delta Logo
9:19 am - 3:47 pm
MDW
-
HPN
5h 28m
1 stop
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
$527Delta
Sat, Jul 25 - Sun, Jul 26
Delta Logo
9:19 am - 3:47 pm
MDW
-
HPN
5h 28m
1 stop
Delta Logo
12:36 pm - 6:25 pm
HPN
-
MDW
6h 49m
1 stop
$533Delta
Fri, Jul 24 - Sun, Aug 2

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Delta flights from Chicago Midway Airport to White Plains

Our best Delta deals on Chicago Midway Airport to White Plains flight tickets
Delta
Aug 21
MDW9:24 amChicago Midway
5h 24m
1 stop
HPN3:48 pmWhite Plains Westchester County
Aug 24
HPN6:00 amWhite Plains Westchester County
6h 51m
1 stop
MDW11:51 amChicago Midway
$395
Delta
Aug 4
MDW6:05 amChicago Midway
4h 58m
1 stop
HPN12:03 pmWhite Plains Westchester County
Sep 2
HPN6:00 amWhite Plains Westchester County
4h 59m
1 stop
MDW9:59 amChicago Midway
$415
Delta
Jul 25
MDW9:19 amChicago Midway
5h 28m
1 stop
HPN3:47 pmWhite Plains Westchester County
Aug 1
HPN12:36 pmWhite Plains Westchester County
6h 31m
1 stop
MDW6:07 pmChicago Midway
$445

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to White Plains 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 June 30, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to White Plains that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 8/21

9:24 am-3:48 pm

1 stop5h 24m

White Plains Westchester County

Mon 8/24

6:00 am-11:51 am

1 stop6h 51m

$395

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 7/28

6:00 am-2:29 pm

1 stop7h 29m

White Plains Westchester County

Tue 8/4

6:00 am-9:59 am

1 stop4h 59m

$415

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 7/25

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Sat 8/1

12:36 pm-6:07 pm

1 stop6h 31m

$445

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 9/18

9:29 am-3:45 pm

1 stop5h 16m

White Plains Westchester County

Tue 9/22

6:00 am-11:55 am

1 stop6h 55m

$459

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 7/18

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Tue 7/21

12:36 pm-6:25 pm

1 stop6h 49m

$475

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 7/21

11:05 am-6:07 pm

1 stop6h 02m

White Plains Westchester County

Mon 7/27

4:29 pm-10:15 pm

1 stop6h 46m

$489
Quickest round-trip

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 9/4

9:24 am-3:48 pm

1 stop5h 24m

White Plains Westchester County

Sun 9/6

6:00 am-10:10 am

1 stop5h 10m

$503

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 7/9

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Wed 7/15

10:29 am-4:15 pm

1 stop6h 46m

$519

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 7/25

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Sun 7/26

12:36 pm-6:25 pm

1 stop6h 49m

$527

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 7/24

9:19 am-3:47 pm

1 stop5h 28m

White Plains Westchester County

Sun 8/2

12:36 pm-6:25 pm

1 stop6h 49m

$533

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 Chicago Midway Airport to White Plains

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 White Plains?

According to our data, Saturday is the cheapest day to fly to White Plains from Chicago Midway Airport. The lowest ticket price found for a Saturday departure recently was $450. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around $550. These prices are subject to change though, so be sure to set up a Price Alert for flights to White Plains.

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

The cheapest time of day to fly to White Plains is in the morning when flights can be purchased for as low as $481. In the afternoon is when there is more demand to fly to White Plains, so prices are often more expensive at around $511 per ticket.

When to book flights from Chicago Midway Airport to White Plains

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

Cheap Chicago Midway Airport to White Plains (MDW to HPN) flight deals and tips

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

Fastest flight time

4h 58m

Direct flights

None
The fastest flight from Chicago Midway Airport to White Plains takes 4h 58m
There are no direct flights from Chicago Midway Airport to White Plains. There are no popular flight routes from Chicago Midway Airport to White Plains.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to White Plains

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

    Chicago Midway and White Plains Westchester County are 725.1 mi apart from one another. By plane, this route typically takes 4h 58m.

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

    Prices for flights from Chicago Midway Airport to White Plains Westchester County Airport refresh daily.

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

  • What documentation or ID do you need to fly to White Plains Westchester County Airport?

    The travel and health documents required for your trip to White Plains Westchester County Airport 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 White Plains Westchester County Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to White Plains from Chicago.

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

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

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

Once all potential Chicago to White Plains flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to White Plains from Chicago 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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