Find Cheap Flights from White Plains Westchester County to Chicago (HPN - CHI)

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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: Wed Sep 20 2017 Return: Mon Sep 25 2017 Trip spans 6 days
Delta
Delta
HPN
MDW
3h 50m
1 stop
MDW
HPN
3h 51m
1 stop
Depart: Sun Nov 5 2017 Return: Sat Nov 11 2017 Trip spans 7 days
American Airlines
American Airlines
HPN
ORD
2h 30m
nonstop
ORD
HPN
2h 15m
nonstop
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
United
United
HPN
ORD
2h 34m
nonstop
ORD
HPN
2h 13m
nonstop
Depart: Thu Aug 17 2017 Return: Sat Aug 19 2017 Trip spans 3 days
Major Airline
Major Airline
HPN
ORD
15h 12m
nonstop
ORD
HPN
27h 30m
nonstop
Depart: Sat Oct 21 2017 Return: Tue Oct 24 2017 Trip spans 4 days
Delta
Delta
HPN
MDW
6h 11m
1 stop
MDW
HPN
3h 56m
1 stop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
Delta
Delta
HPN
MDW
3h 50m
1 stop
MDW
HPN
3h 56m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 28 2017 Trip spans 13 days
Delta
Delta
HPN
MDW
4h 21m
1 stop
MDW
HPN
3h 51m
1 stop
Depart: Thu Aug 10 2017 Return: Sat Aug 12 2017 Trip spans 3 days
United
United
HPN
ORD
2h 36m
nonstop
ORD
HPN
2h 20m
nonstop
Depart: Wed Jul 12 2017 Return: Sun Jul 16 2017 Trip spans 5 days
American Airlines
American Airlines
HPN
ORD
7h 27m
1 stop
ORD
HPN
9h 55m
1 stop
Depart: Wed Aug 16 2017 Return: Mon Aug 28 2017 Trip spans 13 days
Delta
Delta
HPN
ORD
4h 08m
1 stop
ORD
HPN
3h 51m
1 stop
Depart: Fri Sep 1 2017 Return: Sun Sep 3 2017 Trip spans 3 days
United
United
HPN
ORD
2h 41m
nonstop
ORD
HPN
2h 20m
nonstop
Depart: Sat Jul 29 2017 Return: Sun Aug 6 2017 Trip spans 9 days
Major Airline
Major Airline
HPN
ORD
22h 26m
nonstop
ORD
HPN
26h 25m
nonstop
Depart: Tue Nov 14 2017 Return: Mon Nov 20 2017 Trip spans 7 days
Delta
Delta
HPN
MDW
3h 50m
1 stop
MDW
HPN
5h 42m
1 stop
Depart: Sat Sep 9 2017 Return: Mon Sep 11 2017 Trip spans 3 days
United
United
HPN
ORD
2h 36m
nonstop
ORD
HPN
2h 14m
nonstop
Depart: Fri Oct 20 2017 Return: Tue Oct 24 2017 Trip spans 5 days
United
United
HPN
ORD
2h 31m
nonstop
ORD
HPN
2h 12m
nonstop
Depart: Fri Sep 1 2017 Return: Tue Sep 5 2017 Trip spans 5 days
Delta
Delta
HPN
MDW
3h 50m
1 stop
MDW
HPN
3h 56m
1 stop
Depart: Thu Jun 29 2017 Return: Sat Jul 1 2017 Trip spans 3 days
Major Airline
Major Airline
HPN
ORD
2h 28m
nonstop
ORD
HPN
0h 28m
nonstop
Depart: Thu Oct 26 2017 Return: Mon Oct 30 2017 Trip spans 5 days
United
United
HPN
ORD
2h 31m
nonstop
ORD
HPN
2h 12m
nonstop
Depart: Fri Dec 8 2017 Return: Sun Dec 10 2017 Trip spans 3 days
United
United
HPN
ORD
2h 31m
nonstop
ORD
HPN
2h 12m
nonstop
Depart: Mon Jun 26 2017 Return: Thu Jun 29 2017 Trip spans 4 days
Major Airline
Major Airline
HPN
ORD
2h 28m
nonstop
ORD
HPN
0h 28m
nonstop
Direct flights HPN to CHI on American Airlines
Flight # Depart HPN Arrive ORD Sun Mon Tue Wed Thu Fri Sat Valid Between
3804 7:00 am 8:27 am Jun 21 - Aug 21
3804 7:00 am 8:27 am Jun 24 - Aug 19
3297 4:39 pm 6:11 pm Jun 21 - Jul 4
3297 4:39 pm 6:11 pm Jun 24 - Aug 20
3297 4:39 pm 6:11 pm Jul 5 - Aug 21
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

White Plains
$184
Destination

Chicago
only $240
only $184
Airlines Airline reviews

17 travelers who booked a flight from White Plains to Chicago rated their chosen airlines with an average of 6.8.

Overall
6.8
Boarding
6.7
Crew
7.5
Comfort
6.6
Food
6.6
Entertainment
6.2