
Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to White Plains (HPN). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $451 (Delta) |
One-way from | $168 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $292 |
Fly from
Fly to
Route
Depart
Return
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Mon 12/7
5:02 pm-11:27 am
3 stops17h 25m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Fri 12/11
5:02 pm-9:00 pm
2 stops26h 58m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Mon 11/16
4:31 pm-9:00 pm
3 stops27h 29m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 12/9
12:39 pm-4:35 pm
1 stop26h 56m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Thu 12/10
6:00 am-10:11 pm
1 stop15h 11m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Tue 2/16
9:46 am-4:30 pm
1 stop5h 44m
White Plains Westchester County
Tue 2/23
12:32 pm-6:08 pm
1 stop6h 36m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Sat 12/5
11:28 am-6:00 pm
1 stop5h 32m
White Plains Westchester County
Sat 12/12
6:00 am-10:28 am
1 stop5h 28m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 1/13
9:38 am-3:49 pm
1 stop5h 11m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Tue 1/12
6:00 am-12:04 pm
1 stop5h 04m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 11/25
6:00 am-12:13 pm
1 stop5h 13m
White Plains Westchester County
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
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