Private charter · MDW → PSF
Chicago to Great Barrington
742 miles. One price for the whole airplane.
Price your flight from Chicago to Great Barrington
The trip
Chicago to Great Barrington, door to door faster.
Trade about 16 hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Pittsfield Municipal Airport in Great Barrington, 742 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.
- Distance
- 742 mi
- Flight
- —
- Driving
- 16 hours
- Passengers
- Up to 1
Departing Chicago
Airports in Chicago
MDW
Major airportChicago Midway International Airport
Chicago · KMDW
- From downtown
- 9 mi
- Longest runway
- 6,522 ft
ORD
Major airportChicago O'Hare International Airport
Chicago · KORD
- From downtown
- 16 mi
- Longest runway
- 13,000 ft
PWK
Commercial airportChicago Executive Airport
Chicago/Prospect Heights/Wheeling · KPWK
- From downtown
- 21 mi
- Longest runway
- 5,001 ft
GYY
Commercial airportGary/Chicago International Airport
Gary · KGYY
- From downtown
- 21 mi
- Longest runway
- 8,859 ft
Arriving Great Barrington
Airports in Great Barrington
PSF
Regional airportPittsfield Municipal Airport
Pittsfield · KPSF
- From downtown
- 16 mi
- Longest runway
- 5,792 ft
HCC
Regional airportColumbia County Airport
Hudson
- From downtown
- 19 mi
- Longest runway
- 5,350 ft
When you land
Things to do in Great Barrington
Great Barrington is the main town of the southern Berkshires, a compact downtown of restored brick buildings, independent shops and restaurants set along the Housatonic River. Much of its economy depends on the second-home owners, weekenders and remote workers who have turned the surrounding countryside into one of the most desirable corners of New England, along with farms, small food producers, real estate and the arts. Bard College at Simon’s Rock and the Mahaiwe Performing Arts Center add a cultural life that lasts well beyond summer.
- 01
Mahaiwe Performing Arts Center
A restored 1905 theater on Main Street presents concerts, dance, comedy, film and live opera and theater broadcasts throughout the year.
- 02
Monument Mountain
Just north of town, popular trails climb to a rocky quartzite summit with sweeping views of the southern Berkshires; Herman Melville and Nathaniel Hawthorne famously hiked here together in 1850.
- 03
Bash Bish Falls
Near Mount Washington in the state’s far southwest corner, the tallest single-drop waterfall in Massachusetts plunges through a granite gorge into a clear pool.
- 04
Norman Rockwell Museum
In nearby Stockbridge, the museum holds the world’s largest collection of Rockwell’s original art, along with the studio he used, moved to the museum grounds.
- 05
Butternut and Catamount
Two family-friendly ski areas sit close to town, with Catamount straddling the New York state line and offering night skiing and a summer aerial adventure park.
- 06
Ashintully Gardens
In Tyringham, the Trustees maintain a contemplative mid-century garden of terraces, fountains and lawns created by composer John McLennan beside the ruins of an early 20th-century marble mansion.
Questions
Chicago to Great Barrington flights
How long is a private flight from Chicago to Great Barrington?
About a short flight in a private jet, for 742 miles direct. Driving the same trip takes about 16 hours.
Which airports do flights from Chicago to Great Barrington use?
You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Pittsfield Municipal Airport (PSF) or Columbia County Airport (HCC). Pick whichever is closest to where you're starting and where you're headed.
How much does a private charter from Chicago to Great Barrington cost?
The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.
Can I book a round trip between Chicago and Great Barrington?
Yes. Choose round trip when you search, and pick your return date and time. Flights from Great Barrington back to Chicago are priced the same way.
Return flight
Great Barrington to Chicago
More flights from Chicago
More flights to Great Barrington
Explore Chicago private charter and Great Barrington private charter, airports and things to do. Arriving at Pittsfield Municipal Airport (PSF).
Chicago to Great Barrington, on your schedule
Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.
Get an instant price