4.9
4.6Journey information
Overview: Chicago, IL to Pittsfield, MA flight
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Flights from Chicago, IL to Pittsfield, MA depart on average 45 times per day, taking around 2h 12m. Cheap flight tickets for this journey start at $375 (€307) but you can travel from only $125 (€102) by bus.
There are 5 flights per day. The earliest flight runs at 05:00, the last at 21:38. The fastest flight covers the 738 miles (1188 km) distance in 2h 10m. July is the cheapest month to fly.
Distance 738 miles (1188 km) |
Average flight duration 2h 12m |
Cheapest ticket price $375 (€307) |
Flights per day 45 |
Direct flights 5 |
Fastest flight 2h 10m |
First flight 5:00 AM |
Last flight 9:38 PM |
Cheapest Month Jul |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 77 days |
The cheapest and fastest flights from Chicago, IL to Pittsfield, MA
Cheapest price
$375
Average price
$375
Fastest journey
2 h 11 m
Average duration
2 h 11 m
Flights per day
1
Distance
1188 km
The best way to find a cheap flight ticket from Chicago, IL to Pittsfield, MA is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Chicago, IL to Pittsfield, MA will cost around $375 if you buy it on the day, but the cheapest tickets can be found for only $375.
Of the 1 flights that leave Chicago, IL for Pittsfield, MA onSat, Jun 27, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Jun 27 the direct flights cover the 1188 km distance in an average of 2 h 11 m but if you time it right, some flights will get you there in just 2 h 11 m .
On Sat, Jun 27 the longest flights will take 2 h 11 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
2:19 AM2h11Chicago, IL4:30 AMPittsfield, MA$3751One-way0 transfers
- 2:19 AM2h11Chicago, IL4:30 AMPittsfield, MA$3751One-way0 transfers
Travel Information
Compare train, bus, and flight for Chicago, IL to Pittsfield, MA
Omio recommends booking the train as it is the most popular option from Chicago, IL to Pittsfield, MA among Omio's users. If you are prioritising price take the bus with prices starting from $125. For those with little time consider booking a flight which can get you there in 2h 12m. The ticket price range depends on the travel mode: a bus costs an average of $125, and a train costs an average of $261.
Distance: 738 miles (1188 km)
Compare flight with
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$429 Average price | $539 Average price | $138 Average price Cheapest | $173 Average price (fuel + tolls) |
5h 12m Average total duration Fastest 2h 12m Onboard + 3h 0m Additional time* | 18h 30m Average total duration 18h 0m Onboard + 30m Additional time* | 42h 20m Average total duration 41h 50m Onboard + 30m Additional time* | 12h 59m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Pittsfield, MA:
A bus is $290 (€238) less than a flight for this route with tickets for a flight from Chicago, IL to Pittsfield, MA costing on average $429 (€351).
A bus is $401 (€328) less than a train for this route with tickets for a train from Chicago, IL to Pittsfield, MA costing on average $539 (€441).
Other travel options to Pittsfield, MA take longer:
Train takes on average 18h 0m.
Bus takes on average 41h 50m.
Live departures
Chicago, IL to Pittsfield, MA flight times
The table below shows live departures for Chicago, IL to Pittsfield, MA flights for tomorrow, Sunday, June 21. You can also manually refresh the results below to see updated flight journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 2:19 AM Chicago, IL | 2h11 | 4:30 AM Pittsfield, MA | 0 transfersDirect | |
This is the last flight of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Pittsfield, MA by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
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Jun 27
FAQs: Chicago, IL to Pittsfield, MA Flight
Find answers to the most common questions about traveling from Chicago, IL to Pittsfield, MA by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Pittsfield, MA, this guide helps you travel smarter and with confidence.
- Pittsfield Fourth of July Celebration, a festive event featuring fireworks, parades, and community activities to celebrate Independence Day
- Pittsfield Arts Festival, an annual celebration of local artists with exhibitions, performances, and workshops
- Berkshire International Film Festival, a showcase of independent films from around the world with screenings and discussions.
- Independence Day, vibrant fireworks and festive parades celebrating American heritage
- Labor Day, pleasant weather perfect for outdoor activities and local events
- Thanksgiving, a cozy atmosphere with family gatherings and community festivities.
popular airports
Popular airports from Chicago, IL to Pittsfield, MA
Most Chicago, IL to Pittsfield, MA flights use the O'Hare International Airport to Bradley International Airport airport pair. Use this guide to compare Chicago, IL and Pittsfield, MA airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Which Chicago, IL airport do flights to Pittsfield, MA leave from?
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport airport facilities and services
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food and drink
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
More options for your journey from Chicago, IL to Pittsfield, MA
Here are some other resources that might have the information you need
Most popular flights to and from Pittsfield, MA and Chicago, IL
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