- Recommended
MASS MoCA
Contemporary art museum in a converted mill featuring changing exhibitions, installations, and strong ties to North Adams culture.
2,000+ travel companies
2,000+ travel companies
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
4.942K ratings
Google Play
4.6136K reviews
The cheapest and fastest buses from Chicago, IL to Pittsfield, MA
Showing times, prices and bookable tickets for Sep 19
Cheapest price on Sep 19
€171
Average ticket price on Sep 19
€171
Fastest journey on Sep 19
1 d 19 h 20 m
Average journey duration on Sep 19
1 d 19 h 20 m
Buses on Sep 19
1
Distance
1188 km
Cheap tickets
The best way to find a cheap bus 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 €171 if you buy it on the day, but the cheapest tickets can be found for only €171.
Fast buses
It's difficult to get from Chicago, IL to Pittsfield, MA without transferring at least once.
7:15 PM43h20Chicago, IL2:35 PMPittsfield, MA€1711One-way1 transfer
- 7:15 PM43h20Chicago, IL2:35 PMPittsfield, MA€1711One-way1 transfer
Travel Information
Compare train, bus, and flight for Chicago, IL to Pittsfield, MA
Omio recommends booking the flight 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 an average ticket price of €165 For those with little time, consider booking a flight, which has an average total journey time of 5h 59m. Average ticket prices depend on the travel mode: a bus costs an average of €165, while a flight costs an average of €722.
Distance: 738 miles (1188 km)
Compare bus with
| Bus | Most popular Flight | Train | Driving |
|---|---|---|---|
€165 Average price Cheapest | €722 Average price | €248 Average price | €143 Average price (fuel + tolls) |
31h 25m Average total duration 30h 55m Onboard + 30m Additional time* | 5h 59m Average total duration Fastest 3h 59m Onboard + 2h 0m Additional time* | 18h 13m Average total duration 17h 43m Onboard + 30m Additional time* | 12h 59m Average total duration (door-to-door) |
 Most popular bus company |  Most popular airline |  Most popular train company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Chicago, IL to Pittsfield, MA is a bus with an average price of €165.
This is compared to other travel options from Chicago, IL to Pittsfield, MA:
A bus is €83 less than a train for this route with tickets for a train from Chicago, IL to Pittsfield, MA costing on average €248.
A bus is €557 less than a flight for this route with tickets for a flight from Chicago, IL to Pittsfield, MA costing on average €722.
The fastest way to travel from Chicago, IL to Pittsfield, MA is by flight with an average journey time of 3h 59m.
Other travel options to Pittsfield, MA take longer:
Train takes on average 17h 43m.
Bus takes on average 30h 55m.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Pittsfield, MA including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Chicago, IL to Pittsfield, MA among Omio's users.
Take the bus. It's the cheapest way to make this trip, and the price gap is usually bigger than people expect.
Tickets start at around €165 compared to roughly €143 in fuel and tolls — a saving of about €-21.49. The journey takes 30h 55m versus 12h 59m by car, so you'll arrive a bit later, but you can use the time productively rather than spending it behind the wheel. No parking to sort, no fuel stops, and most coaches have Wi-Fi and power outlets.
Driving is worth considering if you're on a tight schedule, travelling as a group (where fuel costs split several ways), or want the flexibility to stop along the way.
Chicago, IL to Pittsfield, MA Bus Timetables
| Operator | Departure Time | Arrival Time | Duration | Departure days | Cheapest price |
|---|---|---|---|---|---|
Operator Greyhound | Departure Time 03:50AM | Arrival Time 09:40PM | Duration 41h50 | Departure days Mon, Tue, Fri | Cheapest price €102 |
Operator Flixbus USA | Departure Time 07:15PM | Arrival Time 02:35PM | Duration 43h20 | Departure days Tue, Wed, Fri, Sat | Cheapest price €171 |
Live departures
Chicago, IL to Pittsfield, MA bus times
The table below shows live departures for Chicago, IL to Pittsfield, MA buses for tomorrow, Saturday, September 19. You can also manually refresh the results below to see updated bus journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 7:15 PM Chicago, IL | 43h20 | 2:35 PM Pittsfield, MA | 1 transfer | |
This is the last bus 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.
Sat
Sep 19
Sep 19
Sun
Sep 20
Sep 20
Mon
Sep 21
Sep 21
Tue
Sep 22
Sep 22
Wed
Sep 23
Sep 23
Thu
Sep 24
Sep 24
Fri
Sep 25
Sep 25
Why should you book Chicago, IL to Pittsfield, MA buses with Omio?
Greyhound operates all buses services from Chicago, IL to Pittsfield, MA.
Omio is an official ticket reseller for all your travel options from Chicago, IL to Pittsfield, MA.
Why book with Omio vs Greyhound?
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Greyhound with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago, IL to Pittsfield, MA.
Why book with Omio over Wanderu?
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago, IL to Pittsfield, MA.
Journey information
Overview: Bus from Chicago, IL to Pittsfield, MA
USAUSA
Buses from Chicago, IL to Pittsfield, MA run on average 2 times per day, taking around 30h 55m. Cheap bus tickets for this journey start at €160 if you book in advance.
The earliest bus runs at 06:55, the last at 23:15. The fastest bus covers the 738 miles (1188 km) distance in 29h 10m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 738 miles (1188 km) |
Average bus duration 30h 55m |
Cheapest ticket price €160 |
Buses per day 2 |
Fastest bus 29h 10m |
First bus 6:55 AM |
Last bus 11:15 PM |
Cheapest Month Aug |
Cheapest Day Mon |
High Season Jan - Mar |
Low Season Apr - Jun |
Best time to book 77 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Bus providers: Greyhound from Chicago, IL to Pittsfield, MAYou can travel by bus between Chicago, IL to Pittsfield, MA with Greyhound for as low as €160. When you search for schedules and tickets, Omio will show you the best journey
Greyhound
About
Greyhound Lines, Inc. is a prominent American intercity bus transportation provider, established in 1914. It operates the largest intercity bus network in the United States, also extending services to Canada and Mexico. Greyhound is known for offering affordable and reliable long-distance travel, connecting major cities and rural communities across North America. The company's buses are equipped with amenities such as free Wi-Fi, power outlets, and extra legroom to enhance passenger comfort. Greyhound is a subsidiary of Flix SE, which also owns FlixBus, and together they offer an extensive network of over 1,600 destinations.
Luggage & cancellation policy
Average Greyhound Duration
29h 10m
Cheapest Greyhound Price
€160
Greyhound frequency
2 a day
Luggage included
One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Additional luggage
$15 per additional bag.
Cancellation Policy
You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Amenities on board the bus
Wifi
Food sold onboard
Seat reservation
Toilets
USB plugs
Accessibility
Assistance; Priority seating; Wheelchair-accessible buses.
Bikes
Bikes are allowed.
Complete guide to Pittsfield, MA
Things to do in Pittsfield, MA
Discover the best of Pittsfield, MA — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Pittsfield, MA trip today.
- Recommended
The Mount
Historic house museum in nearby Lenox presenting author Edith Wharton’s home, gardens, and design-focused exhibitions.
- Recommended
Ventfort Hall Mansion and Gilded Age Museum
Gilded Age museum inside Ventfort Hall with exhibits on regional history, domestic life, and the Berkshires’ summer estates.
- Recommended
Upstreet Cultural District
Downtown Pittsfield district with shops, public art, theaters, and event spaces, ideal for walking and experiencing local life.
- Recommended
Burbank Park on Onota Lake
Large city park with ponds, trails, athletic fields, and mountain views, popular for walks, picnics, and seasonal events.
- Recommended
Berry Pond and Balance Rock
Wooded reservation with hiking trails and a summit observation tower offering broad views over Pittsfield and the Berkshires.
FAQs: Bus from Chicago, IL to Pittsfield, MA
Find answers to the most common questions about traveling from Chicago, IL to Pittsfield, MA by bus. 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 bus, the cheapest option, or tips for making the most of your visit at Pittsfield, MA, this guide helps you travel smarter and with confidence.
Cheap bus tickets from Chicago, IL to Pittsfield, MA can start from as little as €160 when you book in advance. The average bus ticket price for Chicago, IL to Pittsfield, MA is €165 ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by bus from Chicago, IL to Pittsfield, MA is 29h 10m to travel the 738 miles (1188 km) long journey. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest bus from Chicago, IL to Pittsfield, MA leaves at 6:55 AM. Plan your trip with the Journey Planner from Omio.
The latest bus from Chicago, IL to Pittsfield, MA leaves at 11:15 PM.
There are 2 buses a day from Chicago, IL to Pittsfield, MA which require at least one change with Greyhound. Schedules can vary on holidays or weekends with fewer buses.
When taking a bus from Chicago, IL to Pittsfield, MA, you can count on Greyhound for the best way to get you to Pittsfield, MA. You can also check all possible bus companies who offer a service between Chicago, IL and Pittsfield, MA and compare the amenities they offer before buying a bus ticket.
When departing from Chicago, IL , you have various bus station options to start your journey from including Chicago, Greyhound Bus Station, Chicago, Union Station (Amtrak), IL . When arriving in Pittsfield, MA , you can end your journey in bus stations like Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) .Passengers board the bus most frequently from Chicago, Greyhound Bus Station, which is located around 1 miles (2 km) away from the city centre, and they get off the bus at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal), located 0 away from the city centre.
A trip to Pittsfield, MA from Chicago, IL is worth doing but not as a day trip with a journey time of 29h 10m each way. Check with Omio app the best way to travel.
The cheapest month for a bus from Chicago, IL to Pittsfield, MA is August.
It's helpful to compare your options as there are 3 ways to travel between Chicago, IL and Pittsfield, MA including taking a train, bus, and flight.
Yes, the following accessibility options are available when taking the bus from Chicago, IL to Pittsfield, MA:
- Greyhound
- Assistance
- Priority seating
- Wheelchair-accessible buses.
Yes, there are bathrooms on board the bus from Chicago, IL to Pittsfield, MA for bus company Greyhound.
Yes, bikes are allowed on board the bus with bus company Greyhound.
Whether you can cancel your bus ticket from Chicago, IL to Pittsfield, MA depends on the bus companies:
- Greyhound
- You can cancel your ticket for a refund or exchange up to 24 hours before departure, for a cancellation fee applied.
Tickets are often cheaper when booked early. Traveling during off-peak hours or on weekdays can help you save money. Sort results by price to quickly identify the most affordable options. Check for promotions or discounts available on our website and app.
Yes, there is food available to purchase on board the bus from Chicago, IL to Pittsfield, MA.
Yes, the following luggage options are included when booking a bus ticket from Chicago, IL to Pittsfield, MA:
- Greyhound
- One carry-on bag up to 25 lbs (11 kg) and one checked bag up to 50 lbs (23 kg).
Yes, the following additional luggage options are available when booking a bus ticket from Chicago, IL to Pittsfield, MA:
- Greyhound
- $15 per additional bag.
Unfortunately, pets are not allowed on the bus from Chicago, IL to Pittsfield, MA.
You can reserve your seat on the bus from Chicago, IL to Pittsfield, MA with the following bus company: Greyhound
Yes, there are USB plugs on board the bus from Chicago, IL to Pittsfield, MA with the following bus company: Greyhound.
Yes, there is Wifi on board the bus from Chicago, IL to Pittsfield, MA with the following bus company: Greyhound.
Since neither Chicago, IL nor Pittsfield, MA are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
We recommend using the flight as it is the most popular way to get from Chicago, IL to Pittsfield, MA among Omio's users.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Pittsfield, MA, travelers should be mindful of typical urban safety concerns such as petty theft and vehicle break-ins, especially in busy areas or parking lots. It is advisable to stay alert in crowded places and avoid poorly lit streets at night. While there are no widespread reports of specific scams targeting visitors, travelers should be cautious of common scams like overcharging by taxis or unfamiliar vendors. Using reputable transportation services and securing personal belongings can help ensure a safe visit.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular bus stations
Popular bus stations from Chicago, IL to Pittsfield, MA
Most Chicago, IL to Pittsfield, MA buses use the Chicago, Greyhound Bus Station to Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) station pair. Use this guide to compare Chicago, IL and Pittsfield, MA bus stations on this route, check city-centre transport, alongside checking practicalities like bus station facilities and services.
Departure bus stations in Chicago
Arrival bus stations in Pittsfield
Which Chicago, IL station do buses to Pittsfield, MA leave from?
Buses from Chicago, IL to Pittsfield, MA leave from Chicago, Greyhound Bus Station. The station is 1 miles (3 km) from Chicago, IL city centre at 630 W Harrison St, Chicago, IL 60607, USA.
Chicago, Greyhound Bus Station630 W Harrison St, Chicago, IL 60607, USA
City-centre transport
Getting to Chicago, Greyhound Bus Station from Chicago city centre
Chicago, Greyhound Bus Station is 2 km from Chicago city centre. Public transport options include:
Bus7 · 8m · €3 · every ~6 min
Chicago, Greyhound Bus Station bus station facilities and services
Chicago, Greyhound Bus Station has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Snack shop and vending machines available
Wi-Fi and ATMs
Free Wi-Fi in waiting area. ATMs are located near entrance.
Tickets and information
Ticket office support is available at Chicago, Greyhound Bus Station.
Parking, taxis and toilets
Available at Chicago, Greyhound Bus Station: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Greyhound Bus Station: Wheelchair accessible entrances and seating.
Chicago, Union Station (Amtrak)Chicago Union Station, 225 S Canal St, Chicago, IL 60606, USA
City-centre transport
Getting to Chicago, Union Station (Amtrak) from Chicago city centre
Chicago, Union Station (Amtrak) is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · €3 · every ~13 min
Chicago, Union Station (Amtrak) bus station facilities and services
Chicago, Union Station (Amtrak) has practical services for this route, including Wifi, Parking, Dining, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Food and drink
Food options include: Multiple dining options are available inside the station.
Wi-Fi and ATMs
Free Wi-Fi is available in waiting areas. ATMs are aTMs are located near the main entrance.
Tickets and information
Ticket office support is available at Chicago, Union Station (Amtrak).
Parking, taxis and toilets
Available at Chicago, Union Station (Amtrak): Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Chicago, Union Station (Amtrak): Station is accessible with elevators and ramps.
Which Pittsfield, MA station do buses from Chicago, IL arrive at?
Buses from Chicago, IL to Pittsfield, MA arrive at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal). Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) is 0 miles (1 km) from Pittsfield, MA city centre.
Pittsfield, Columbus Ave (Joseph Scelsi Intermodal)Joseph Scelsi Intermodal Transportation Center, 1 Columbus Ave, Pittsfield, MA 01201, USA
City-centre transport
Getting to Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) from Pittsfield city centre
TRUE
Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) bus station facilities and services
Pittsfield, Columbus Ave (Joseph Scelsi Intermodal) has practical services for this route, including Wifi, Parking, ATM, Taxis, Accessibility, WC, Shower, and Ticket Office.
Wi-Fi and ATMs
Free public Wi-Fi available. ATMs are available at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal).
Tickets and information
Ticket office support is available at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal).
Parking, taxis and toilets
Available at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal): Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Pittsfield, Columbus Ave (Joseph Scelsi Intermodal): Wheelchair accessible entrances and exits.
Most popular bus connections from Chicago, IL
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 buses to and from Pittsfield, MA and Chicago, IL
Most popular bus connections to Pittsfield, MA
The Omio App Makes Travel Planning Easy
We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.
