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Cheap flights from Chicago Midway Airport to New York from $141

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 1/19. 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 Chicago Midway Airport to New York

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
6:25 am - 2:26 pmMDW-HPN
7h 01m1 stop
Delta Logo
4:29 pm - 10:22 pmHPN-MDW
6h 53m1 stop
$369Delta
Find Deal
Sat, Jan 24 - Tue, Jan 27
Delta Logo
12:48 pm - 3:49 pmMDW-HPN
26h 01m2 stops
Delta Logo
5:15 pm - 10:22 pmHPN-MDW
6h 07m1 stop
$381Delta
Find Deal
Wed, Jan 28 - Sat, Jan 31
Delta Logo
9:32 am - 3:49 pmMDW-HPN
5h 17m1 stop
Delta Logo
6:00 am - 11:59 amHPN-MDW
6h 59m1 stop
$400Delta
Find Deal
Fri, Jan 23 - Tue, Jan 27
Delta Logo
11:21 am - 6:00 pmMDW-HPN
5h 39m1 stop
Delta Logo
5:12 pm - 8:52 amHPN-MDW
16h 40m1 stop
$418Delta
Find Deal
Tue, Jan 6 - Fri, Jan 9
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
Delta Logo
6:00 am - 10:27 amHPN-MDW
5h 27m1 stop
$431Delta
Find Deal
Tue, Dec 30 - Tue, Jan 6
Delta Logo
9:32 am - 3:49 pmMDW-HPN
5h 17m1 stop
Delta Logo
5:12 pm - 8:52 amHPN-MDW
16h 40m1 stop
$449Delta
Find Deal
Mon, Jan 5 - Fri, Jan 9
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
Delta Logo
12:55 pm - 5:26 pmHPN-MDW
5h 31m1 stop
$465Delta
Find Deal
Tue, Dec 30 - Sat, Jan 3
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
Delta Logo
5:20 pm - 11:47 pmHPN-MDW
7h 27m1 stop
$469Delta
Find Deal
Tue, Dec 9 - Sat, Dec 13
Delta Logo
9:34 am - 3:49 pmMDW-HPN
5h 15m1 stop
Delta Logo
6:50 pm - 11:47 pmHPN-MDW
5h 57m1 stop
$506Delta
Find Deal
Tue, Dec 9 - Sun, Dec 14
Delta Logo
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
Delta Logo
6:55 pm - 10:07 pmHPN-MDW
28h 12m1 stop
$518Delta
Find Deal
Tue, Dec 30 - Sun, Jan 4

Delta flights from Chicago Midway Airport to White Plains

Our best Delta deals on Chicago Midway Airport to White Plains flight tickets
Delta
Jan 24
MDW6:25 amChicago Midway
7h 01m
1 stop
HPN2:26 pmWhite Plains Westchester County
Jan 31
HPN5:15 pmWhite Plains Westchester County
6h 07m
1 stop
MDW10:22 pmChicago Midway
$369
Find similar
Delta
Jan 28
MDW12:48 pmChicago Midway
26h 01m
2 stops
HPN3:49 pmWhite Plains Westchester County
Jan 31
HPN5:15 pmWhite Plains Westchester County
6h 07m
1 stop
MDW10:22 pmChicago Midway
$381
Find similar
Delta
Jan 23
MDW9:32 amChicago Midway
5h 17m
1 stop
HPN3:49 pmWhite Plains Westchester County
Jan 27
HPN6:00 amWhite Plains Westchester County
6h 59m
1 stop
MDW11:59 amChicago Midway
$400
Find similar

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 November 29, 2025.
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

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 1/24

6:25 am-2:26 pm

1 stop7h 01m

White Plains Westchester County

Tue 1/27

4:29 pm-10:22 pm

1 stop6h 53m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 1/28

12:48 pm-3:49 pm

2 stops26h 01m

White Plains Westchester County

Sat 1/31

5:15 pm-10:22 pm

1 stop6h 07m

$381

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 1/23

9:32 am-3:49 pm

1 stop5h 17m

White Plains Westchester County

Tue 1/27

6:00 am-11:59 am

1 stop6h 59m

$400

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 1/6

11:21 am-6:00 pm

1 stop5h 39m

White Plains Westchester County

Fri 1/9

5:12 pm-8:52 am

1 stop16h 40m

$418

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/30

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

Tue 1/6

6:00 am-10:27 am

1 stop5h 27m

$431

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Mon 1/5

9:32 am-3:49 pm

1 stop5h 17m

White Plains Westchester County

Fri 1/9

5:12 pm-8:52 am

1 stop16h 40m

$449

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/30

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

Sat 1/3

12:55 pm-5:26 pm

1 stop5h 31m

$465

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/9

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Sat 12/13

5:20 pm-11:47 pm

1 stop7h 27m

$469

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/9

9:34 am-3:49 pm

1 stop5h 15m

White Plains Westchester County

Sun 12/14

6:50 pm-11:47 pm

1 stop5h 57m

$506

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/30

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

Sun 1/4

6:55 pm-10:07 pm

1 stop28h 12m

$518

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, Tuesday is the cheapest day to fly to White Plains from Chicago Midway Airport. The lowest ticket price found for a Tuesday departure recently was $419. 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 Monday because tickets tend to average around $823. 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 at noon when flights can be purchased for as low as $460. In the evening is when there is more demand to fly to White Plains, so prices are often more expensive at around $493 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

5h 00m

Direct flights

None
The fastest flight from Chicago Midway Airport to White Plains takes 5h 00m
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.
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  • 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 5h 00m.

  • 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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