Westchester County to Chicago HPN → ORD, RFD
Westchester County Airport (HPN) → O'Hare International Airport (ORD), Chicago Rockford International Airport (RFD)
The cheapest one-way found recently is $296 with Breeze Airways, 28 Oct, found yesterday.
One-way
The cheapest one-way fare on each of 4 departure dates is usually $272 to $324.
Cheapest one-way found recently
$296
28 Oct · Breeze Airways
Westchester County Airport (HPN) → Chicago Rockford International Airport (RFD)
Leaves 7:45 p.m. · 37 h 9 min trip
2 stops
found yesterday
Cheapest nonstop one-way
None seen yet.
Found recently, and the cheapest we hold
$296 28 Octfound yesterdayOpen this trip
$201 12 Feb 2027found 4 days agoOpen this trip
What have prices looked like?
Over 25 days, 24 Sept to 18 Oct, the cheapest one-way we saw each day was $173 to $340.
25 days is a short history, so treat this range as an early guide.
Those were the prices on those days, not today's.
Is this a good one-way price?
Compared with the cheapest one-way fare on each of 4 departure dates from 24 Oct to 12 Feb 2027, found by travelers' searches in the last 7 days (economy, the price the seller showed on Aviasales). The usual range is the middle half of those prices.
Could nearby dates be cheaper?
No. We hold one-way fares on 1 other departure date within 3 days of 28 Oct, and it is not cheaper.
Every date we hold
4 fares on 4 departure dates
See the chart as a table
| Dates | From | Airline | Airports | Stops | Found | |
|---|---|---|---|---|---|---|
| 24 Oct | $337 | Breeze Airways | Westchester County Airport (HPN) → O'Hare International Airport (ORD) | 2 stops | found 5 days ago | Open this trip |
| 27 Oct | $319 | Breeze Airways | Westchester County Airport (HPN) → O'Hare International Airport (ORD) | 2 stops | found 2 days ago | Open this trip |
| 28 Oct | $296 | Breeze Airways | Westchester County Airport (HPN) → Chicago Rockford International Airport (RFD) | 2 stops | found yesterday | Open this trip |
| 12 Feb 2027 | $201 | Breeze Airways | Westchester County Airport (HPN) → O'Hare International Airport (ORD) | 2 stops | found 4 days ago | Open this trip |
Which month looks cheapest?
February 2027 is the cheapest month — from $201.
Airlines on the cheapest dates: Breeze Airways.
Premium cabin fares from Westchester County to Chicago
We hold no premium economy, business or first-class fares for this route: we collect them for the busiest routes, and this one is not among them yet.
Today's prices for 28 Oct in another cabin: Premium economy · Business · First
How far ahead were prices cheapest for Westchester County to Chicago?
One-way
Not enough history yet: in 25 days of one-way prices, 24 Sept to 18 Oct, fewer than 3 booking ranges had prices on 7 days or more.
Could a nearby airport be cheaper?
A different airport at either end can change the fare — sometimes a lot.
Return
New York → Chicago
41 km from Westchester County
$254
4 Dec – 6 Dec · EWR → ORD · out nonstop, back nonstop
found yesterday
Hartford → Chicago
134 km from Westchester County
$382
29 Oct – 5 Nov · BDL → ORD · out 1 stop, back 1 stop
found today
Newburgh → Chicago
59 km from Westchester County
$427
1 Nov – 6 Nov · SWF → ORD · out 1 stop, back 1 stop
found today
New Haven → Chicago
76 km from Westchester County
$516
22 Oct – 25 Oct · HVN → ORD · out 1 stop, back 2 stops
found 6 days ago
Cheapest recent price on each route — round trip, per traveler in Economy. Distances are in a straight line.
One-way
Hartford → Chicago
134 km from Westchester County
$133
$163 less than flying from Westchester County
21 Nov · BDL → ORD · 1 stop
found 6 days ago
Islip → Chicago
62 km from Westchester County
$160
$136 less than flying from Westchester County
13 Dec · ISP → ORD · 1 stop
found 5 days ago
New York → Chicago
41 km from Westchester County
$164
$132 less than flying from Westchester County
20 Dec · EWR → ORD · nonstop
found yesterday
Newburgh → Chicago
59 km from Westchester County
$382
$86 more than flying from Westchester County
29 Mar 2027 · SWF → MDW · 1 stop
found 2 days ago
Cheapest recent price on each route — one way, per traveler in Economy. Distances are in a straight line.
Live price for these dates
The cheapest one-way found recently is for 28 Oct. A live search on this page shows what those dates cost now, for one adult in economy.
Prices are what travelers' searches on Aviasales found in the last 7 days, in US dollars: the price the seller showed on Aviasales; bags may cost extra. Fares change, so check today's price before you book. How our prices work