- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Cheapest price
$344
Average price
$344
Fastest journey
13 h 38 m
Average duration
13 h 38 m
Trains per day
1
Distance
953 km
The best way to find a cheap train ticket from Greenwood, MS 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 Greenwood, MS to Chicago, IL will cost around $344 if you buy it on the day, but the cheapest tickets can be found for only $344.
Of the 1 trains that leave Greenwood, MS for Chicago, IL on Thu, Aug 06, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Aug 06 the direct trains cover the 953 km distance in an average of 13 h 38 m but if you time it right, some trains will get you there in just 13 h 38 m .
On Thu, Aug 06 the slowest trains will take 13 h 38 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.


Omio recommends booking the train as it is the most popular option from Greenwood, MS to Chicago, IL among Omio's users. If you are prioritising price take the train with prices starting from $130. For those with little time consider booking a train which can get you there in 13h 32m. The ticket price range depends on the travel mode: a train costs an average of $130, and a train costs an average of $130.
Distance: 592 miles (953 km)
Most popular Train | Driving |
|---|---|
$175 Average price Cheapest | $47 Average price (fuel + tolls) |
14h 2m Average total duration Fastest 13h 32m Onboard + 30m Additional time* | 9h 42m Average total duration (door-to-door) |
![]() Most popular train company | Your own car or car rental |
Direct Options | Direct Options |
Tickets start at around $175 compared to roughly $47 in fuel and tolls — a saving of about $-127.72. The journey takes 13h 32m versus 9h 42m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
The table below shows live departures for Greenwood, MS to Chicago, IL trains for today, Wednesday, August 5. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
58 City Of New Orleans | 5:38 PM Greenwood Amtrak Station, Greenwood, MS | 13h37 | 7:15 AM Chicago Union Station, Chicago, IL | 0 transfersDirect | |
58 City Of New Orleans · 390 Saluki | 5:38 PM Greenwood Amtrak Station, Greenwood, MS | 19h22 | 1:00 PM Chicago Union Station, Chicago, IL | 1 transfer | |
58 City Of New Orleans · 392 Illini | 5:38 PM Greenwood Amtrak Station, Greenwood, MS | 28h07 | 9:45 PM Chicago Union Station, Chicago, IL | 1 transfer | |
58 City Of New Orleans · 390 Saluki | 5:38 PM Greenwood Amtrak Station, Greenwood, MS | 19h22 | 1:00 PM Chicago Union Station, Chicago, IL | 1 transfer | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
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.
Trains from Greenwood, MS to Chicago, IL run on average 3 times per day, taking around 13h 32m. Cheap train tickets for this journey start at $130 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 37m.
Distance 592 miles (953 km) |
Average train duration 13h 32m |
Cheapest ticket price $130 |
Trains per day 3 |
Direct trains 1 |
Fastest train 13h 37m |
First train 8:15 AM |
Last train 9:05 PM |
Cheapest Month Feb |
Cheapest Day Tue |
High Season Jul - Sep |
Low Season Jan - Mar |
Busiest Day Tue |
Least Busy Day Tue |
Best time to book 14 days |
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Find answers to the most common questions about traveling from Greenwood, MS 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.

Most Greenwood, MS to Chicago, IL trains use the Greenwood Amtrak Station to Union Station station pair. Use this guide to compare Greenwood, MS and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like 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 options are available at Greenwood Amtrak Station.
Ticket office support is available at Greenwood Amtrak Station. Information desks are located in the main hall.
Available at Greenwood Amtrak Station: Parking, Taxis, WC.
Accessibility facilities are available at Greenwood Amtrak Station: Ramps.
Union Station is 3 km from Chicago city centre. Public transport options include:
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 options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Here are some other resources that might have the information you need