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Cheap train tickets from Greenwood to Chicago

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Greenwood to Chicago Train Schedule

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Trip Summary

3 trains operate daily from Greenwood to Chicago. The train trip from Greenwood to Chicago is usually about 19 hours and 6 minutes long. However, traveling on the fastest Amtrak City of New Orleans train can get you there in as little as 13 hours and 38 minutes.

Distance594 mi (956 km)
Fastest train13h 38m
Lowest price$93.00
Trains per day1
Most frequent serviceAmtrak
Train lines2

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Price trends for trains from Greenwood to Chicago

Monthly avg. prices

$150$120$90$60$30MAMJJASONDJF

Prices as travel date approaches

$175$140$105$70$353020100

Which train should you take from Greenwood to Chicago?

2 train services operate from Greenwood to Chicago. Amtrak usually has more trains scheduled, with 2 trips per day. That said, it's still worth comparing the prices and trip durations:

TrainDaily TripsAvg. TimeAvg. Price
Amtrak221h 51m$106.46
Amtrak City of New Orleans113h 38m$105.24
  • Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 2 Amtrak trains from Greenwood to Chicago every day, as well as 2 trips on the weekends, with prices starting from $93.

  • The City of New Orleans is an Amtrak route that runs daily trains from Chicago to New Orleans and vice versa. The City of New Orleans includes a sightseer lounge with panoramic windows for the best views of the five states along the route. Affordable Coach seats cost about for a trip from Greenwood to Chicago. However, the City of New Orleans also offers private roomettes and bedrooms for added comfort and luxury (and a higher price). Passengers who book sleeper accommodations will enjoy included meals, and all passengers can stop into the cafe car to purchase meals and snacks.

Frequently asked questions about traveling by train from Greenwood to Chicago

The distance between Greenwood and Chicago is approximately 594 miles, or 956 kilometers. The average train journey between these two cities takes 19 hours and 6 minutes, although the absolute fastest you could get there is 13 hours and 38 minutes.

Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.

Trains from Greenwood to Chicago are the most crowded on Monday. Tickets also tend to be more expensive then. If you are looking for a great deal on your train tickets or just want extra room to stretch out, consider traveling on Friday instead, as it tends to be the least crowded day of the week.

The earliest train departs Greenwood at 5:00pm while the last train of the day leaves at 7:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

There are 3 scheduled trains on most days. There is one direct train, which you can stay on for the entire journey from Greenwood to Chicago. In contrast, taking a non-direct train would require you to transfer trains during your trip.

You can also take a train for your return trip from Chicago to Greenwood.

City Information

Greenwood

Greenwood, MS, US - GWD-0

Image credit: U.S. Department of Agriculture

Link to image attribution

Greenwood is a city in Mississippi, at the eastern edge of the Mississippi Delta region. It is also called the Cotton Capital of the World and is the center of the civil rights movement in the United States. Greenwood was pushed under the national spotlight after the murder of Emmett Louis Till. This triggered civil rights movements in the city, and you can pay your respects at the Emmett Till Historical Marker. Greenwood features diverse historical sites and museums like the Fort Pemberton Memorial Park and Museum of the Mississippi Delta. You can expect a gorgeous view from the Tallahatchie Bridge or take walks on the Mississippi Blues Trail.

Greenwood is constantly organizing festivals like the AgFest celebrating the agriculture community and the Stars & Stripes Festival, which pays tribute to veterans. The downtown area is the best place to explore and is highly walkable, so you can take a self-guided tour and visit the local stores and restaurants. Once night falls, you can check out the theatres and arenas for shows or have craft beers at some of their cafés and bars.

Amtrak has daily trips to Greenwood from nearby cities. Bus lines are provided within the town by the Mississippi Department of Transportation.

Chicago

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Station Information

Where is the train station in Greenwood?

Main departure station: Carrollton Ave and E Gibson St

There is one train station in Greenwood.

All train stations in Greenwood:

  • Carrollton Ave and E Gibson St

Where is the train station in Chicago?

Chicago, IL - Union Station - CHIUST-0

Image credit: Jeramey Jannene

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Main arrival station: Chicago (Union Station), Illinois

The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.

All train stations in Chicago:

  • Chicago (Union Station), Illinois

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