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Find Flight Deals from White Plains Westchester County to Chicago (HPN - CHI)

Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from White Plains Westchester County to Chicago

(Round-trip)
Depart: Sat Jun 13 2015 Return: Sun Jun 14 2015 Trip spans 2 days
US Airways
US Airways
HPN
2:54p
ORD
3:30a
12h 36m
1 stop
ORD
5:14a
HPN
7:30a
2h 16m
nonstop
Depart: Wed Feb 18 2015 Return: Tue Feb 24 2015 Trip spans 7 days
American Airlines
American Airlines
HPN
5:25a
ORD
8:10a
2h 45m
nonstop
ORD
9:50a
HPN
12:02p
2h 12m
nonstop
Depart: Thu Feb 19 2015 Return: Sun Feb 22 2015 Trip spans 4 days
American Airlines
American Airlines
HPN
2:00a
ORD
4:59a
2h 59m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Fri Feb 20 2015 Return: Sun Feb 22 2015 Trip spans 3 days
US Airways
US Airways
HPN
1:30p
ORD
4:18p
2h 48m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Sat Feb 21 2015 Return: Mon Mar 2 2015 Trip spans 10 days
US Airways
US Airways
HPN
11:37a
ORD
2:25p
2h 48m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Sun Feb 22 2015 Return: Sun Mar 1 2015 Trip spans 8 days
US Airways
US Airways
HPN
11:37a
ORD
2:25p
2h 48m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Thu Feb 26 2015 Return: Sun Mar 1 2015 Trip spans 4 days
US Airways
US Airways
HPN
5:25a
ORD
8:10a
2h 45m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Fri Feb 27 2015 Return: Sun Mar 1 2015 Trip spans 3 days
US Airways
US Airways
HPN
5:25a
ORD
8:10a
2h 45m
nonstop
ORD
1:45a
HPN
3:53a
2h 08m
nonstop
Depart: Mon Mar 2 2015 Return: Tue Mar 10 2015 Trip spans 8 days
American Airlines
American Airlines
HPN
5:25a
ORD
8:10a
2h 45m
nonstop
ORD
8:55a
HPN
11:07a
2h 12m
nonstop
Depart: Tue Mar 3 2015 Return: Wed Mar 11 2015 Trip spans 8 days
American Airlines
American Airlines
HPN
5:25a
ORD
8:10a
2h 45m
nonstop
ORD
10:50a
HPN
1:02p
2h 12m
nonstop
Depart: Wed Apr 15 2015 Return: Sun Apr 19 2015 Trip spans 5 days
US Airways
US Airways
HPN
8:54a
ORD
11:30a
2h 36m
nonstop
ORD
2:30p
HPN
4:52p
2h 22m
nonstop
Depart: Thu Apr 16 2015 Return: Sun Apr 19 2015 Trip spans 4 days
US Airways
US Airways
HPN
3:29a
ORD
6:09a
2h 40m
nonstop
ORD
2:30p
HPN
4:52p
2h 22m
nonstop
Depart: Fri Apr 17 2015 Return: Sun Apr 19 2015 Trip spans 3 days
US Airways
US Airways
HPN
3:29a
ORD
6:09a
2h 40m
nonstop
ORD
2:30p
HPN
4:52p
2h 22m
nonstop
Depart: Sat Apr 18 2015 Return: Sun Apr 19 2015 Trip spans 2 days
US Airways
US Airways
HPN
8:54a
ORD
11:30a
2h 36m
nonstop
ORD
2:30p
HPN
4:52p
2h 22m
nonstop
Depart: Fri Apr 24 2015 Return: Sun Apr 26 2015 Trip spans 3 days
American Airlines
American Airlines
HPN
2:59p
ORD
5:24p
2h 25m
nonstop
ORD
5:14a
HPN
7:30a
2h 16m
nonstop
Depart: Sat Apr 25 2015 Return: Fri May 1 2015 Trip spans 7 days
American Airlines
American Airlines
HPN
8:59a
ORD
11:30a
2h 31m
nonstop
ORD
5:14a
HPN
7:30a
2h 16m
nonstop
Depart: Sun Apr 26 2015 Return: Fri May 8 2015 Trip spans 13 days
American Airlines
American Airlines
HPN
8:59a
ORD
11:30a
2h 31m
nonstop
ORD
2:48p
HPN
5:03p
2h 15m
nonstop
Depart: Sat Feb 14 2015 Return: Mon Feb 16 2015 Trip spans 3 days
Delta
Delta
HPN
4:00a
MDW
8:37a
4h 37m
1 stop
MDW
7:40a
HPN
1:27p
5h 47m
1 stop
Depart: Mon Feb 16 2015 Return: Wed Feb 18 2015 Trip spans 3 days
Delta
Delta
HPN
11:29a
ORD
4:07p
4h 38m
1 stop
ORD
2:00a
HPN
8:54a
6h 54m
1 stop
Depart: Fri Jun 5 2015 Return: Sun Jun 7 2015 Trip spans 3 days
United
United
HPN
8:00a
ORD
10:23a
2h 23m
nonstop
ORD
9:30a
HPN
11:42a
2h 12m
nonstop
Change your search
Direct flights HPN to CHI on American Airlines
Flight # Depart HPN Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3051 7:00 am 8:59 am Jan 29 - Mar 6
3063 10:25 am 12:10 pm Jan 29 - Feb 6
3063 10:25 am 12:10 pm Jan 31 - Feb 28
3063 10:25 am 12:10 pm Feb 8 - Mar 4
3063 10:26 am 12:10 pm Mar 5 - Mar 6
3654 4:37 pm 6:25 pm Jan 29 - Feb 7
3654 4:37 pm 6:25 pm Feb 8 - Mar 7
3686 6:30 pm 8:18 pm Jan 29 - Feb 13
3686 6:30 pm 8:18 pm Feb 16 - Mar 6
Airports
Origin

White Plains
$317
Destination

Chicago
only $317
only $405