Rome2Rio

How to get fromPittsfield to Chicagoby bus, plane, train (Amtrak), bus (Greyhound, Flixbus), car, or train

Find Transport to Chicago

See all options

Pittsfield to Chicago

Rome2Rio compared 7 ways to get from Pittsfield to Chicago. The best route is Bus to Albany County Airport, fly to Chicago Midway International Airport, a distance of 1185.709 km.

  1. Bus to Albany County Airport, fly to Chicago Midway International Airport

    best
    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago Midway International Airport (MDW)plane plane ALB - MDW
    5h 58m
    $121–619

  2. Train to Bradley International Airport, fly to Chicago O'Hare International Airport

    cheapest
    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago O'Hare International Airport (ORD)plane plane BDL - ORD
    7h 38m
    $84–361

  3. Train (Amtrak)

    1. Take the train from Pittsfield Amtrak Station to Chicago Union Stationtrain train Lake Shore Limited
    18h 30m
    $280–600

  4. Bus

    1. Take the bus from Pittsfield to Port Authority Bus Terminalbus bus
    2. Take the bus from Port Authority Bus Terminal to Newark Penn Stationbus bus 108
    3. Take the bus from Newark Penn Station to Chicago Bus Stationbus bus
    22h 12m
    $158–314

  5. Drive 850.7 mi

    1. Drive from Pittsfield to Chicagocar car 850.7 mi
    14h 44m
    $156–225

  6. Bus to Albany County Airport, fly to Chicago O'Hare International Airport

    1. Take the bus from Pittsfield to Albany Bus Terminal, NYbus bus
    2. Fly from Albany County Airport (ALB) to Chicago O'Hare International Airport (ORD)plane plane ALB - ORD
    6h 28m
    $96–469

  7. Train to Bradley International Airport, fly to Chicago Midway International Airport

    1. Take the train from Pittsfield Amtrak Station to Springfieldtrain train
    2. Fly from Bradley International Airport (BDL) to Chicago Midway International Airport (MDW)plane plane BDL - MDW
    7h 9m
    $99–441

Pittsfield to Chicago by train (Amtrak)

Calendar7Weekly Trains
Duration18h 30mAverage Duration
Ticket$280Cheapest Price
See schedules

Questions & Answers

Map of how to get from Pittsfield to Chicago.ExpandLaunch map view
  • Distance: 772.9 mi
  • Duration: 5h 58m

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

Amtrak operates a train from Pittsfield Amtrak Station to Chicago Union Station once daily. Tickets cost $280–600 and the journey takes 18h 30m. Alternatively, you can take a bus from Pittsfield to Chicago Bus Station via Port Authority Bus Terminal and Newark Penn Station in around 22h 12m.

Airlines
Train operators
Bus operators

Want to know more about travelling around United States

Rome2Rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

Related travel guides

Need to know: Greyhound

Read the travel guideNeed to know: Greyhound

More Questions & Answers