Travel within United States is: Fully open. See details.

There are 9 ways to get from Chicago to Pittsfield by plane, bus, train or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Chicago Midway to Albany, bus  •  6h 59m

  1. Fly from Chicago Midway (MDW) to Albany (ALB) MDW - ALB
  2. Take the bus from Albany to Pittsfield

$218 - $419

Cheapest option

Train  •  17h 38m

  1. Take the train from Chicago Union Station to Pittsfield Amtrak Station Lake Shore Limited

$90 - $130

7 alternative options

Fly Chicago O'Hare to Albany, bus  •  7h 16m

  1. Fly from Chicago O'Hare (ORD) to Albany (ALB) ORD - ALB
  2. Take the bus from Albany to Pittsfield

$148 - $309

Fly Chicago Midway to Hartford, train  •  8h 39m

  1. Fly from Chicago Midway (MDW) to Hartford (BDL) MDW - BDL
  2. Take the train from Hartford Amtrak Station to Springfield
  3. Take the train from Springfield to Pittsfield Amtrak Station

$200 - $2,104

Fly Chicago O'Hare to Hartford, train  •  8h 58m

  1. Fly from Chicago O'Hare (ORD) to Hartford (BDL) ORD - BDL
  2. Take the train from Hartford Amtrak Station to Springfield
  3. Take the train from Springfield to Pittsfield Amtrak Station

$210 - $584

Fly Chicago O'Hare to Syracuse, train  •  10h 25m

  1. Fly from Chicago O'Hare (ORD) to Syracuse (SYR) ORD - SYR
  2. Take the train from Syracuse Regional Transportation Center to Pittsfield Amtrak Station

$186 - $432

Fly Chicago Midway to Manchester, bus, train  •  10h 15m

  1. Fly from Chicago Midway (MDW) to Manchester (MHT) MDW - MHT
  2. Take the bus from North Londonderry, NH - exit 5 to Boston South Buses
  3. Take the train from Boston South Station to Pittsfield Amtrak Station

$224 - $676

Bus  •  18h 48m

  1. Take the bus from Chicago, IL to New York
  2. Take the bus from Chinatown-152 East Broadway to Albany, NY Nyc
  3. Take the bus from Albany to Pittsfield

$125 - $152

Drive  •  14h 36m

  1. Drive from Chicago to Pittsfield 856.7 miles

$80 - $130

Chicago → Pittsfield
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Rules to follow in United States

2m

Recommended

Travel within United States

Domestic border crossings may be subject to approval, testing and quarantine
Nationwide control measures in place

COVID-19 help in United States

If you need help, visit the national COVID-19 website or call the COVID-19 Helpline 800-232-4636

Frequently Asked Questions


Yes, travel within United States is currently allowed.

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Domestic travel is not restricted, but some conditions may apply

  • Face masks are recommended
  • There is a social distancing requirement of 2 metres
  • Domestic border crossings may be subject to approval, testing and quarantine
  • Nationwide control measures in place

Explore travel options

The national COVID-19 helpline number in Pittsfield is 800-232-4636.

Wearing a face mask on public transport in Pittsfield is recommended.

The social distance requirement in Pittsfield is 2 metres.

Make yourself known to an official member of staff and/or call the national coronavirus helpline number on 800-232-4636.

Last updated: 16 Jun 2021
Exceptions may apply, for full details: Centers for Disease control and prevention (CDC).

We're working around the clock to bring you the latest COVID-19 travel updates.
This information is compiled from official sources. To the best of our knowledge, it is correct as of the last update.
Visit Rome2rio travel advice for general help.

Questions & Answers

The cheapest way to get from Chicago to Pittsfield is to drive which costs $80 - $130 and takes 14h 36m.

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The quickest way to get from Chicago to Pittsfield is to fly and bus which costs $210 - $420 and takes 6h 59m.

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No, there is no direct bus from Chicago to Pittsfield. However, there are services departing from Chicago, IL and arriving at Pittsfield via Chinatown-152 East Broadway, Central Ave & Lexington Ave and Albany. The journey, including transfers, takes approximately 18h 48m.

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Yes, there is a direct train departing from Chicago Union Station station and arriving at Pittsfield Amtrak Station station. Services depart once daily, and operate every day. The journey takes approximately 17h 38m.

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The distance between Chicago and Pittsfield is 741 miles. The road distance is 856.7 miles.

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The best way to get from Chicago to Pittsfield without a car is to train which takes 17h 38m and costs $90 - $130.

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It takes approximately 6h 59m to get from Chicago to Pittsfield, including transfers.

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Chicago to Pittsfield bus services, operated by D&W Bus, depart from Chicago, IL station.

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Chicago to Pittsfield train services, operated by Amtrak, depart from Chicago Union Station.

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The best way to get from Chicago to Pittsfield is to train which takes 17h 38m and costs $90 - $130. Alternatively, you can bus, which costs $120 - $160 and takes 18h 48m.

Mode details

Map of how to get from Chicago to Pittsfield.
Launch map view
  • Distance: 741.1 miles
  • Duration: 6h 59m

What companies run services between Chicago, IL, USA and Pittsfield, MA, USA?

Amtrak operates a train from Chicago Union Station to Pittsfield Amtrak Station once daily. Tickets cost $90 - $130 and the journey takes 17h 38m. Alternatively, you can take a bus from Chicago to Pittsfield via New York, Chinatown-152 East Broadway, Albany, NY, Central Ave & Lexington Ave, Madison Ave & Green Street, and Albany in around 18h 48m.

Airlines
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Albany
Ave. Duration
1h 50m
When
Every day
Estimated price
$130 - $470
Flights from Chicago Midway to Albany via Baltimore
Ave. Duration
4h 15m
When
Every day
Estimated price
$140 - $500
Flights from Chicago O'Hare to Albany via Baltimore
Ave. Duration
4h 25m
When
Saturday
Estimated price
$120 - $430
Flights from Chicago Midway to Hartford
Ave. Duration
1h 58m
When
Every day
Estimated price
$120 - $430
Flights from Chicago Midway to Hartford via Baltimore
Ave. Duration
4h 22m
When
Every day
Estimated price
$120 - $450
Flights from Chicago Midway to Manchester
Ave. Duration
2h 2m
When
Every day
Estimated price
$140 - $550
Flights from Chicago Midway to Manchester via Baltimore
Ave. Duration
4h 25m
When
Saturday
Estimated price
$150 - $550
United Airlines
Website
united.com
Flights from Chicago O'Hare to Albany
Ave. Duration
1h 57m
When
Every day
Estimated price
$180 - $800
Flights from Chicago O'Hare to Albany via Newark
Ave. Duration
4h 19m
When
Every day
Estimated price
$180 - $800
Flights from Chicago O'Hare to Albany via Washington Dulles
Ave. Duration
4h 35m
When
Every day
Estimated price
$180 - $800
Flights from Chicago O'Hare to Hartford
Ave. Duration
2h 6m
When
Every day
Estimated price
$230 - $950
Flights from Chicago O'Hare to Hartford via Washington Dulles
Ave. Duration
4h 26m
When
Every day
Estimated price
$230 - $950
Flights from Chicago O'Hare to Syracuse
Ave. Duration
1h 53m
When
Every day
Estimated price
$280 - $850
Flights from Chicago O'Hare to Syracuse via Washington Dulles
Ave. Duration
4h 22m
When
Every day
Estimated price
$280 - $850
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Albany
Ave. Duration
2h 6m
When
Every day
Estimated price
$180 - $600
Flights from Chicago O'Hare to Albany via Philadelphia
Ave. Duration
4h 41m
When
Every day
Estimated price
$180 - $600
Flights from Chicago O'Hare to Albany via Charlotte
Ave. Duration
4h 49m
When
Every day
Estimated price
$180 - $600
Flights from Chicago O'Hare to Hartford
Ave. Duration
2h 14m
When
Every day
Estimated price
$230 - $650
Flights from Chicago O'Hare to Hartford via Reagan Washington
Ave. Duration
4h 23m
When
Every day
Estimated price
$230 - $650
Flights from Chicago O'Hare to Syracuse
Ave. Duration
1h 54m
When
Every day
Estimated price
$310 - $750
Flights from Chicago O'Hare to Syracuse via Reagan Washington
Ave. Duration
4h 15m
When
Every day
Estimated price
$310 - $750
Flights from Chicago O'Hare to Syracuse via Philadelphia
Ave. Duration
4h 21m
When
Every day
Estimated price
$310 - $750
Delta
Website
delta.com
Flights from Chicago Midway to Albany via Detroit
Ave. Duration
3h 58m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$65 - $480
Flights from Chicago O'Hare to Albany via Detroit
Ave. Duration
4h 25m
When
Every day
Estimated price
$55 - $420
Flights from Chicago Midway to Hartford via Detroit
Ave. Duration
4h 22m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$60 - $440
Flights from Chicago O'Hare to Hartford via Detroit
Ave. Duration
4h 19m
When
Every day
Estimated price
$50 - $380
Flights from Chicago O'Hare to Syracuse via Detroit
Ave. Duration
4h 10m
When
Every day
Estimated price
$55 - $470
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Hartford Amtrak Station to Springfield
Ave. Duration
39 min
Frequency
Every 4 hours
Estimated price
$22 - $35
Schedules at
amtrak.com
Coach Seat
$22 - $35
Premium
$170 - $250
Flexi Coach Seat
$30 - $45
Business Seat
$27 - $40
Train from Springfield to Pittsfield Amtrak Station
Ave. Duration
1h 16m
Frequency
Once daily
Estimated price
$24 - $35
Schedules at
amtrak.com
Coach Seat
$24 - $35
Premium
$180 - $250
Flexi Coach Seat
$35 - $55
Business Seat
$30 - $45
Train from Syracuse Regional Transportation Center to Pittsfield Amtrak Station
Ave. Duration
4h 45m
Frequency
Once daily
Estimated price
$35 - $55
Schedules at
amtrak.com
Coach Seat
$35 - $55
Premium
$200 - $280
Flexi Coach Seat
$60 - $90
Business Seat
$60 - $90
Train from Boston South Station to Pittsfield Amtrak Station
Ave. Duration
3h 49m
Frequency
Once daily
Estimated price
$30 - $50
Schedules at
amtrak.com
Coach Seat
$30 - $50
Premium
$190 - $270
Flexi Coach Seat
$50 - $80
Business Seat
$50 - $75
Train from Chicago Union Station to Pittsfield Amtrak Station
Ave. Duration
17h 38m
Frequency
Once daily
Estimated price
$90 - $130
Schedules at
amtrak.com
Coach Seat
$90 - $130
Premium
$310 - $430
Flexi Coach Seat
$180 - $270
Business Seat
$190 - $270
Amtrak Northeast Regional

Amtrak’s Northeast Regional train service serves the US’ busy northeast corridor from Virginia to Massachusetts; major stops include Boston, Providence, New York City, Philadelphia, Washington DC and Baltimore. Amenities include Wi-Fi, a quiet car, cafe and business-class seating, and travelling with a small dog or cat is permitted. Book at least 14 days in advance for a cheaper Saver Fare.

Rome2rio's guide to Amtrak Northeast Regional
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Hartford Amtrak Station to Springfield
Ave. Duration
47 min
Frequency
Once daily
Estimated price
$35 - $60
Schedules at
amtrak.com
Reserved Coach Seat
$35 - $60
Business Class Seat
$55 - $100
Bus operators
Greyhound USA

Greyhound is a leading bus company based in Dallas, Texas, serving over 3800 destinations across North America, Mexico and Canada. Greyhound carries around 18 million passengers a year who travel 5.4 billion miles (8.6 billion km) a year on their fleet of around 1700 vehicles. For travel flexibility, you can board or get off a Greyhound bus at official Greyhound stations, partner stations and curbside stops. There are around 230 Greyhound stations across the US where you can both catch your bus and buy tickets, that are also available on the official website and via the mobile app.

Rome2rio's guide to Greyhound USA
Contact Details
Phone
+1 214-849-8100/1-800-231-2222
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Albany to Pittsfield
Ave. Duration
1h
Frequency
Once daily
Estimated price
$11 - $17
Website
greyhound.com
Economy
$11 - $17
Flexible
$28 - $40
Peter Pan Bus Lines
Phone
1-800-343-9999
Website
peterpanbus.com
Bus from Albany Greyhound Bus Terminal, Albany, NY to Intermodal Transportation Center, Pittsfield, MA
Ave. Duration
1h
Frequency
3 times a week
Estimated price
$14 - $20
Website
peterpanbus.com
Boston Express
Phone
1800-639-8080
Email
contact@bostonexpressbus.com
Website
bostonexpressbus.com
Bus from North Londonderry, NH - exit 5 to Boston South Buses
Ave. Duration
1h
Frequency
Hourly
Estimated price
$12 - $18
Schedules at
bostonexpressbus.com
Book at
webstore.bostonexpressbus.com
D&W Bus
Website
gotobus.com
Bus from Chicago, IL to New York
Ave. Duration
12h 15m
Frequency
3 times a week
Estimated price
$90 - $110
Schedules at
gotobus.com
Book at
gotobus.com
Fox Bus
Website
gotobus.com
Bus from Chinatown-152 East Broadway to Albany, NY
Ave. Duration
3h 15m
Frequency
Every 3 hours
Estimated price
$20
Schedules at
gotobus.com

Want to know more about travelling around United States

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More Questions & Answers

The quickest flight from Chicago Midway Airport to Albany Airport is the direct flight which takes 1h 50m.

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Chicago to Pittsfield bus services, operated by Greyhound USA, arrive at Pittsfield station.

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Pittsfield is 1h ahead of Chicago. It is currently 6:12 PM in Chicago and 7:12 PM in Pittsfield.

Chicago to Pittsfield train services, operated by Amtrak, arrive at Pittsfield Amtrak Station.

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Yes, the driving distance between Chicago to Pittsfield is 857 miles. It takes approximately 14h 36m to drive from Chicago to Pittsfield.

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Delta and Southwest Airlines offer flights from Chicago Midway Airport to Albany Airport.

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Book your Chicago to Pittsfield train tickets online with Omio.

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There are 70+ hotels available in Pittsfield. Prices start at $100 USD per night.

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The best way to get from Chicago to Chicago Midway Airport is to subway which takes 23 min and costs $2 - $5.

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