Next bus departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Bus | John Oliver Transp. Bus Stop | Downtown Greyhound Station | Cheapest | ||||
| Bus | John Oliver Transp. Bus Stop | Downtown Greyhound Station | Fastest | ||||
| Bus | John Oliver Transp. Bus Stop | 537-517 W. Jackson Blvd | No tags | ||||
Greyhound Lines, Inc. + FlixBus | Bus | John Oliver Transp. Bus Stop | Chicago 95Th & Dan Ryan | No tags | ||||
| Bus | John Oliver Transp. Bus Stop | 537-517 W. Jackson Blvd | No tags |
Last refresh of the prices: Today at 10:34 AM EST.
Compare 2 ways to go from Greenfield to Chicago
Among the sustainable travel choices, the bus stands out as the good way to reach Chicago. The journey takes about 1 day, 6 hours 40 minutes and with fares starting at just $124, it presents an excellent value for a comfortable ride.
Where are the popular stops in Greenfield and Chicago?
Stops in Chicago
- A630 W Harrison St, Chicago, IL 60607, USA
- C
Polk St & Canal St
500-536 W Polk St, Chicago IL 60607, USA - D
Tornado Bus S Kedzie Ave
2807 S Kedzie Ave, Chicago, IL 60623, USA - E
Cumberland CTA
5800 N Cumberland Ave, Chicago, IL 60631, USA - F
Turimex California Ave
2139 S California Ave, Chicago, IL 60608, USA
Compare bus companies
Greyhound Lines offers the most comprehensive intercity bus services in the United States. They operate a modern, environmentally friendly fleet that serves more than 2400 destinations and carries nearly 16 million passengers annually. When traveling with them, you can expect free WiFi, onboard entertainment, bathrooms, power outlets and decent legroom. One of the great perks of Greyhound is that they connect big cities and smaller towns in the US, where you usually can't get to by train or plane. If you're looking for safe and affordable transportation, Greyhound is a great choice.
Frequently asked questions about traveling from Greenfield, MA, US to Chicago by bus
Please note that schedules, routes, or operator details shown here may be updated or vary at the time of your trip.
How much is the bus ticket from Greenfield to Chicago?
The cheapest bus tickets from Greenfield to Chicago start from $124. The average price for this route is around $138. Busbud recommends that you book your tickets in advance for a better chance to get the lowest possible price.
How long is the bus ride from Greenfield to Chicago?
The average bus trip duration from Greenfield to Chicago is 1d 6h, covering a distance of 770 miles (1241 km). The quickest bus can get you there in 1d 2h and is operated by Greyhound.
Which bus companies service the Greenfield to Chicago route?
Several major train operators operate on this route with 5 trains available per day.
What is the earliest and latest departure time for the bus from Greenfield to Chicago?
The earliest bus departs from Greenfield to Chicago at 8:30am. And the latest bus departs at 5:10pm.
What are the CO₂ emissions for the bus trip from Greenfield to Chicago?
A bus trip from Greenfield to Chicago generates an estimated 31 kg of CO₂, making it a highly eco-friendly travel option and recommended mode of travel by Busbud.
Find cheapest prices for buses
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Greenfield, MA, US to Chicago was searched and found on Dec 27, 2025 with a price of $120To save money and be sure you have the best seat, it's a good idea to buy your bus tickets from Greenfield, MA, US to Chicago, as early as possible.
You can expect to pay from $120 to $361 for a bus ticket from Greenfield, MA, US to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at $120 which is on 2025-12-27.
What's the cheapest way to go from Greenfield, MA, US to Chicago?
The bus is the cheapest travel choice for this destination
