The cheapest and fastest trains from Chicago, IL to Greenwood, MS
- Cheapest price on Nov 04
- $150
- Average ticket price on Nov 04
- $167
- Fastest journey on Nov 04
- 17 h 25 m
- Average journey duration on Nov 04
- 21 h 20 m
- Trains on Nov 04
- 2
- Distance
- 953 km
The best way to find a cheap train ticket from Chicago, IL to Greenwood, MS 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 Greenwood, MS will cost around $167 if you buy it on the day, but the cheapest tickets can be found for only $150.
On Wed, Nov 04, we found 2 trains from Chicago, IL to Greenwood, MS, including 2 direct services.
On Wed, Nov 04 the direct trains cover the 953 km distance in an average of 21 h 20 m but if you time it right, some trains will get you there in just 17 h 25 m .
On Wed, Nov 04 the slowest trains will take 1 d 1 h 15 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.

1:15 PM 25h15 Chicago, IL 2:30 PM Greenwood, MS $150 1 One-way 0 transfers
9:05 PM 17h25 Chicago, IL 2:30 PM Greenwood, MS $184 1 One-way 0 transfers

9:05 PM 17h25 Chicago, IL 2:30 PM Greenwood, MS $184 1 One-way 0 transfers
1:15 PM 25h15 Chicago, IL 2:30 PM Greenwood, MS $150 1 One-way 0 transfers
Journey information
Overview: Train from Chicago, IL to Greenwood, MS
Trains from Chicago, IL to Greenwood, MS run on average 4 times per day, taking around 13h 11m. Cheap train tickets for this journey start at $127 if you book in advance.
There are 1 trains per day. The earliest train runs at 08:15, the last at 21:05. The fastest train covers the 592 miles (953 km) distance in 13h 6m.
Distance 592 miles (953 km) |
Average train duration 13h 11m |
Cheapest ticket price $127 |
Trains per day 4 |
Direct trains 1 |
Fastest train 13h 6m |
First train 8:15 AM |
Last train 9:05 PM |
Cheapest Month Feb |
Cheapest Day Mon |
High Season Apr - Jun |
Low Season Oct - Dec |
Best time to book 28 days |
Frequently asked questions about your Chicago, IL to Greenwood, MS trip
Use these quick route answers to check fares, travel time, departure options, and direct services before booking from Chicago, IL to Greenwood, MS.
Live departures
Chicago, IL to Greenwood, MS train times
The table below shows live departures for Chicago, IL to Greenwood, MS trains for today, Tuesday, November 3. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:05 PM Chicago, IL | 17h25 | 2:30 PM Greenwood, MS | 0 transfersDirect | |
| Wednesday, November 4 | |||||
![]() | 1:15 PM Chicago, IL | 25h15 | 2:30 PM Greenwood, MS | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Train companies: Amtrak from Chicago, IL to Greenwood, MS trainsAmtrak trains will get you between Chicago, IL and Greenwood, MS from $127. With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
Companies, tickets, and onboard amenities between Chicago, IL and Greenwood, MS
Review the details behind your booking, from operators and ticket rules to luggage, onboard amenities, accessibility, and route-specific travel policies.
FAQs: Trains from Chicago, IL to Greenwood, MS
Find answers to the most common questions about traveling from Chicago, IL to Greenwood, MS 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 Greenwood, MS, this guide helps you travel smarter and with confidence.

popular train stations
Popular train stations from Chicago, IL to Greenwood, MS
Most Chicago, IL to Greenwood, MS trains use the Union Station to Greenwood Amtrak Station station pair. Use this guide to compare Chicago, IL and Greenwood, MS train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Which Chicago, IL station do trains to Greenwood, MS leave from?
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
Union Station train station facilities and services
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food and drink
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Wi-Fi and ATMs
Free. ATMs are available in the train station.
Tickets and information
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Union Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Union Station: Parking, Taxis, WC.
Bike and car services
Available at Union Station: Bike Parking, Car Rental.
Accessibility
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Shops, hotels and contact
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Which Greenwood, MS station do trains from Chicago, IL arrive at?
Getting to Greenwood Amtrak Station from Greenwood city centre
Greenwood Amtrak Station train station facilities and services
Greenwood Amtrak Station has practical services for this route, including Parking, Dining, Taxis, Accessibility, WC, Ticket Office, Information Desk, and Luggage Carts.
Food and drink
Food and drink options are available at Greenwood Amtrak Station.
Tickets and information
Ticket office support is available at Greenwood Amtrak Station. Information desks are located in the main hall.
Parking, taxis and toilets
Available at Greenwood Amtrak Station: Parking, Taxis, WC.
Accessibility
Accessibility facilities are available at Greenwood Amtrak Station: Ramps.
Train stations for Chicago, IL to Greenwood, MS
Check train stations information for Chicago, IL and Greenwood, MS, including where trains depart and arrive on this route.
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Greenwood, MS
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