
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 5, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $421 (Delta) |
One-way from | $146 (Kiwi.com) |
Popular in | October |
Cheapest in | January |
Average price | $275 |
Fly from
Fly to
Route
Depart
Return
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Tue 12/15
12:28 pm-9:00 pm
3 stops31h 32m
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 11/30
1:16 pm-9:00 pm
2 stops30h 44m
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 11/10
6:08 am-9:00 pm
2 stops13h 52m
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
Sat 12/5
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
Thu 12/3
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
Wed 12/30
9:29 am-3:49 pm
1 stop5h 20m
White Plains Westchester County
Tue 1/5
4:29 pm-10:17 pm
1 stop6h 48m
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-6:03 pm
1 stop6h 31m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Thu 12/31
9:29 am-11:56 am
1 stop25h 27m
White Plains Westchester County
Wed 1/6
12:40 pm-6:00 pm
1 stop6h 20m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Wed 12/9
9:37 am-3:48 pm
1 stop5h 11m
White Plains Westchester County
Wed 12/16
6:40 pm-1:01 pm
2 stops19h 21m
ChicagoWhite Plains
MDW Chicago Midway - HPN White Plains Westchester County
MDWHPN
Chicago Midway
Sat 12/12
9:37 am-3:48 pm
1 stop5h 11m
White Plains Westchester County
Mon 12/14
3:08 pm-1:01 pm
2 stops22h 53m
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
Find useful and relevant information for your journey from Midway to White Plains. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.