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Cheap flights from Chicago Midway Airport to New York from $123

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 10/20. 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
9:29 am - 3:49 pmMDW-HPN
5h 20m1 stop
Delta Logo
4:19 pm - 9:46 pmHPN-MDW
6h 27m1 stop
$369Delta
Find Deal
Sat, Dec 20 - Sat, Jan 17
Delta Logo
6:00 am - 12:11 pmMDW-HPN
5h 11m1 stop
Delta Logo
12:45 pm - 6:34 pmHPN-MDW
6h 49m1 stop
$400Delta
Find Deal
Wed, Apr 1 - Sat, Apr 4
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
Delta Logo
6:41 pm - 9:52 amHPN-MDW
16h 11m1 stop
$421Delta
Find Deal
Sat, Nov 8 - Mon, Nov 10
Delta Logo
2:00 pm - 11:50 amMDW-HPN
20h 50m2 stops
Delta Logo
12:45 pm - 6:34 pmHPN-MDW
6h 49m1 stop
$465Delta
Find Deal
Wed, Apr 1 - Sat, Apr 4
Delta Logo
9:34 am - 3:49 pmMDW-HPN
5h 15m1 stop
Delta Logo
12:55 pm - 6:00 pmHPN-MDW
6h 05m1 stop
$469Delta
Find Deal
Tue, Dec 2 - Sun, Dec 7
Delta Logo
9:35 am - 4:30 pmMDW-HPN
5h 55m1 stop
Delta Logo
4:29 pm - 10:14 pmHPN-MDW
6h 45m1 stop
$476Delta
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
2:00 pm - 11:50 amMDW-HPN
20h 50m2 stops
Delta Logo
12:45 pm - 6:34 pmHPN-MDW
6h 49m1 stop
$496Delta
Find Deal
Wed, Apr 1 - Sat, Apr 4
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
Delta Logo
6:00 am - 11:55 amHPN-MDW
6h 55m1 stop
$499Delta
Find Deal
Thu, Dec 4 - Sun, Dec 7
Delta Logo
6:00 am - 2:29 pmMDW-HPN
7h 29m1 stop
Delta Logo
6:00 am - 11:52 amHPN-MDW
6h 52m1 stop
$511Delta
Find Deal
Sat, Nov 8 - Sun, Nov 9
Delta Logo
6:00 am - 12:00 pmMDW-HPN
5h 00m1 stop
Delta Logo
4:29 pm - 11:40 pmHPN-MDW
8h 11m1 stop
$513Delta
Find Deal
Fri, Nov 7 - Mon, Nov 10

Delta flights from Chicago Midway Airport to White Plains

Our best Delta deals on Chicago Midway Airport to White Plains flight tickets
Delta
Dec 20
MDW9:29 amChicago Midway
5h 20m
1 stop
HPN3:49 pmWhite Plains Westchester County
Jan 17
HPN4:19 pmWhite Plains Westchester County
6h 27m
1 stop
MDW9:46 pmChicago Midway
$369
Find similar
Delta
Apr 1
MDW6:00 amChicago Midway
5h 11m
1 stop
HPN12:11 pmWhite Plains Westchester County
Apr 4
HPN12:45 pmWhite Plains Westchester County
6h 49m
1 stop
MDW6:34 pmChicago Midway
$400
Find similar
Delta
Nov 8
MDW6:00 amChicago Midway
5h 00m
1 stop
HPN12:00 pmWhite Plains Westchester County
Nov 10
HPN6:41 pmWhite Plains Westchester County
16h 11m
1 stop
MDW9:52 amChicago Midway
$421
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 October 14, 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 12/20

9:29 am-3:49 pm

1 stop5h 20m

White Plains Westchester County

Sat 1/17

4:19 pm-9:46 pm

1 stop6h 27m

$369

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 4/1

6:00 am-12:11 pm

1 stop5h 11m

White Plains Westchester County

Sat 4/4

12:45 pm-6:34 pm

1 stop6h 49m

$400

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 11/8

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Mon 11/10

6:41 pm-9:52 am

1 stop16h 11m

$421

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 4/1

2:00 pm-11:50 am

2 stops20h 50m

White Plains Westchester County

Sat 4/4

12:45 pm-6:34 pm

1 stop6h 49m

$465

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Tue 12/2

9:34 am-3:49 pm

1 stop5h 15m

White Plains Westchester County

Sun 12/7

12:55 pm-6:00 pm

1 stop6h 05m

$469

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 10/31

9:35 am-4:30 pm

1 stop5h 55m

White Plains Westchester County

Mon 11/3

4:29 pm-10:14 pm

1 stop6h 45m

$476

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Wed 4/1

2:00 pm-11:50 am

2 stops20h 50m

White Plains Westchester County

Sat 4/4

12:45 pm-6:34 pm

1 stop6h 49m

$496

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Thu 12/4

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Sun 12/7

6:00 am-11:55 am

1 stop6h 55m

$499

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Sat 11/8

6:00 am-2:29 pm

1 stop7h 29m

White Plains Westchester County

Sun 11/9

6:00 am-11:52 am

1 stop6h 52m

$511

ChicagoWhite Plains

MDW - HPN

MDWHPN

Chicago Midway

Fri 11/7

6:00 am-12:00 pm

1 stop5h 00m

White Plains Westchester County

Mon 11/10

4:29 pm-11:40 pm

1 stop8h 11m

$513

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 New York from

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 $797. 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 $454. 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

Direct flights

None
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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