The cheapest and fastest trains from Greenfield, MA to Chicago, IL
Cheapest price
$338
Average price
$338
Fastest journey
20 h 36 m
Average duration
20 h 36 m
Trains per day
1
Distance
1240 km
The best way to find a cheap train ticket from Greenfield, MA to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Greenfield, MA to Chicago, IL will cost around $338 if you buy it on the day, but the cheapest tickets can be found for only $338.
It's difficult to get from Greenfield, MA to Chicago, IL without transferring at least once.


Live departures
Greenfield, MA to Chicago, IL train times
The table below shows live departures for Greenfield, MA to Chicago, IL trains for tomorrow, Friday, November 7. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 1:36 PM Greenfield, MA | 20h36 | 10:12 AM Chicago, IL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Greenfield, MA to Chicago, IL by train
Compare train 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.
Nov 07
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Nov 11
Nov 12
Nov 13
Journey information
Overview: Train from Greenfield, MA to Chicago, IL
Trains from Greenfield, MA to Chicago, IL run on average 1 times per day, taking around 22h 26m. Cheap train tickets for this journey start at $339 (€276) if you book in advance.
The earliest train runs at 09:15, the last at 21:30. The fastest train covers the 770 miles (1240 km) distance in 20h 36m.
Distance 770 miles (1240 km) |
Average train duration 22h 26m |
Cheapest ticket price $339 (€276) |
Trains per day 1 |
Fastest train 20h 36m |
First train 09:15 |
Last train 21:30 |
Train companies: Amtrak from Greenfield, MA to Chicago, IL trainsAmtrak trains will get you between Greenfield, MA and Chicago, IL from $339 (€276). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Greenfield, MA to Chicago, IL
Find answers to the most common questions about traveling from Greenfield, MA to Chicago, IL by train. 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 train, the cheapest option, or tips for making the most of your visit at Chicago, IL, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Greenfield, MA to Chicago, IL
- 6:00 AM - 10:00 PM Monday - Sunday
- Free
- Parking is available adjacent to the station building.
- Hope & Olive
- People's Pint
- Outside the main entrance.
- Ramps.
- $0.50
- Hampton Inn & Suites Greenfield
- Days Inn by Wyndham Greenfield
- Rodeway Inn
- Located in the main hall
- 10 places, covered
- Located in the main hall
- Free
- The station consists of a main hall with a waiting room and ticketing services, with access to the platform.
- Bus: Franklin Regional Transit Authority (FRTA) services available
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Greenfield, MA to Chicago, IL
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