Browse Origins:
Browse Destinations:

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: Mon Apr 13 2015 Return: Tue Apr 14 2015 Trip spans 2 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Tue Apr 14 2015 Return: Wed Apr 15 2015 Trip spans 2 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Wed Apr 15 2015 Return: Thu Apr 16 2015 Trip spans 2 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Thu Apr 16 2015 Return: Fri Apr 17 2015 Trip spans 2 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
5:05a
→
HPN
7:22a
2h 17m
nonstop
Depart: Fri Apr 17 2015 Return: Tue Apr 21 2015 Trip spans 5 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Sun Apr 19 2015 Return: Tue Apr 21 2015 Trip spans 3 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Thu Apr 23 2015 Return: Sun Apr 26 2015 Trip spans 4 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
5:05a
→
HPN
7:22a
2h 17m
nonstop
Depart: Fri Apr 24 2015 Return: Sun Apr 26 2015 Trip spans 3 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
5:05a
→
HPN
7:22a
2h 17m
nonstop
Depart: Thu Apr 30 2015 Return: Mon May 4 2015 Trip spans 5 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Fri May 1 2015 Return: Mon May 4 2015 Trip spans 4 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
11:05a
→
HPN
1:21p
2h 16m
nonstop
Depart: Sun May 3 2015 Return: Sun May 10 2015 Trip spans 8 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
5:14a
→
HPN
7:30a
2h 16m
nonstop
Depart: Mon May 4 2015 Return: Fri May 8 2015 Trip spans 5 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:37p
2h 38m
nonstop
ORD
5:14a
→
HPN
7:30a
2h 16m
nonstop
Depart: Thu May 7 2015 Return: Sun May 10 2015 Trip spans 4 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
11:00a
→
HPN
1:16p
2h 16m
nonstop
Depart: Wed May 13 2015 Return: Tue May 19 2015 Trip spans 7 days
$200
Select
US Airways
US Airways
HPN
3:20a
→
ORD
5:50a
2h 30m
nonstop
ORD
11:15a
→
HPN
1:30p
2h 15m
nonstop
Depart: Thu May 14 2015 Return: Fri May 15 2015 Trip spans 2 days
$200
Select
US Airways
US Airways
HPN
3:29a
→
ORD
6:09a
2h 40m
nonstop
ORD
11:00a
→
HPN
1:16p
2h 16m
nonstop
Depart: Fri May 15 2015 Return: Sun May 17 2015 Trip spans 3 days
$200
Select
US Airways
US Airways
HPN
2:59p
→
ORD
5:24p
2h 25m
nonstop
ORD
5:14a
→
HPN
7:30a
2h 16m
nonstop
Depart: Tue Mar 24 2015 Return: Tue Mar 31 2015 Trip spans 8 days
$324
Select
American Airlines
American Airlines
HPN
12:37p
→
ORD
3:25p
2h 48m
nonstop
ORD
5:05a
→
HPN
7:22a
2h 17m
nonstop
Depart: Sun Jun 14 2015 Return: Tue Jun 16 2015 Trip spans 3 days
$435
Select
Delta
Delta
HPN
8:35a
→
MDW
3:34p
6h 59m
1 stop
MDW
6:10a
→
HPN
11:47a
5h 37m
1 stop
Depart: Sun Apr 5 2015 Return: Thu Apr 9 2015 Trip spans 5 days
$435
Select
Delta
Delta
HPN
3:25a
→
ORD
10:20a
6h 55m
1 stop
ORD
8:00a
→
HPN
2:30p
6h 30m
1 stop
Depart: Wed Apr 8 2015 Return: Sat Apr 11 2015 Trip spans 4 days
$472
Select
United
United
HPN
2:30a
→
ORD
5:00a
2h 30m
nonstop
ORD
2:00p
→
HPN
4:14p
2h 14m
nonstop
Change your search
Select an airline:  American Airlines
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 ✈ ✈ ✈ ✈ ✈ ✈ Mar 8 - Mar 27
3097 7:29 am 9:09 am ✈ ✈ ✈ ✈ ✈ ✈ Mar 29 - May 8
3063 10:26 am 12:10 pm ✈ ✈ ✈ ✈ ✈ ✈ Mar 8 - Mar 27
3063 10:26 am 12:10 pm ✈ Mar 14 - Mar 28
3215 12:54 pm 2:30 pm ✈ Apr 4 - May 2
3215 12:54 pm 2:30 pm ✈ Mar 29 - May 3
3215 12:54 pm 2:30 pm ✈ ✈ ✈ ✈ ✈ Mar 30 - May 6
3654 4:37 pm 6:25 pm ✈ ✈ ✈ ✈ ✈ ✈ ✈ Mar 8 - Mar 28
3686 6:30 pm 8:18 pm ✈ ✈ ✈ ✈ ✈ Mar 9 - Mar 27
3182 6:59 pm 8:37 pm ✈ ✈ ✈ ✈ ✈ Mar 30 - May 6
Airports
Origin
White Plains
$200
Destination
Chicago
only $200
only $435