Cheap train tickets from Poughkeepsie to Chicago
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Trip Summary
You can pick from 2 daily train trips between Poughkeepsie and Chicago. The average train journey from Poughkeepsie to Chicago takes 18 hours and 50 minutes, but some Amtrak Lake Shore Limited train trips are as short as 18 hours and 2 minutes.
| Distance | 706 mi (1136 km) |
| Fastest train | 18h 2m |
| Lowest price | $119.00 |
| Trains per day | 1 |
| Most frequent service | Amtrak |
| Train lines | 2 |
Price trends for trains from Poughkeepsie to Chicago
Monthly avg. prices
Which train should you take from Poughkeepsie to Chicago?
2 train services operate from Poughkeepsie to Chicago. However, each train line only offers one daily trip.
| Train | Daily Trips | Avg. Time | Avg. Price |
|---|---|---|---|
| Amtrak | 1 | 19h 28m | $208.20 |
| Amtrak Lake Shore Limited | 1 | 18h 2m | $185.75 |
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 1 Amtrak trains from Poughkeepsie to Chicago every day, as well as 1 trips on the weekends, with prices starting from $138.
The Amtrak Lake Shore Limited is an overnight train that runs along some of the best shorelines in the U.S., connecting New York City and Boston with Chicago. The service provides top-tier amenities to its passengers, including free WiFi and dining onboard. The Lake Shore Limited departs from 41 Main St in Poughkeepsie and arrives at Chicago (Union Station), Illinois in Chicago. The route takes about 18 hours and 2 minutes and ticket prices start at $119.
Frequently asked questions about traveling by train from Poughkeepsie to Chicago
The distance between Poughkeepsie and Chicago is approximately 706 miles, or 1136 kilometers. The average train journey between these two cities takes 18 hours and 50 minutes, although the absolute fastest you could get there is 18 hours and 2 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.
On a weekly basis, the greatest number of passengers tend to travel by trains from Poughkeepsie to Chicago on Friday. Tickets for Friday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Saturday. Saturday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.
The earliest train departs Poughkeepsie at 3:00pm while the last train of the day leaves at 3:00pm. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.
Trains leave the station in Poughkeepsie twice a day, so there are a couple of options depending on your preferred travel time. One of these is a direct train, which will typically get you to Chicago faster. While it might still have stops along the way, you will not need to switch trains during your trip.
You can also take a train for your return trip from Chicago to Poughkeepsie.
City Information
Poughkeepsie
Poughkeepsie is nicknamed the second capital of New York for a good reason – the bustling city has breathtaking views of the Hudson River and is a quick weekend destination for New Yorkers. Art buffs can visit the Barrett Art Center and Frances Lehman Loeb Art Center, while history lovers will enjoy the National Register of Historic Places. Poughkeepsie is a true university town with campuses for the Culinary Institute of America, Vassar College, and Marist College. If music is your thing, you can check what's playing at the iconic Barvadon Opera House. The city is also an excellent place for picnics and outdoor activities, especially on the riverfront.
Poughkeepsie is known for its wide range of restaurants, ranging from farm-to-table establishments to breweries and brewpubs. The craft beer scene is upcoming, with beer gardens and pubs to check out. Nightlife keeps the fun going with comedy clubs, champagne bars, and lounges.
Poughkeepsie is easily accessible via Amtrak. The Amtrak Lake Shore Limited, Maple Leaf, Empire Service, and Ethan Allen Express stop in Poughkeepsie en route to New York City, Philadelphia, Rensselaer, Newark, and other cities. The central and busiest station is 41 Main St, and many other trains make stops in and around Poughkeepsie. Poughkeepsie is also accessible by Greyhound buses. Most visitors and locals use the Newburgh Airport, only about 15 miles away, for air travel.
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 Poughkeepsie?
Main departure station: 41 Main St
There is one train station in Poughkeepsie.
All train stations in Poughkeepsie:
41 Main St
Where is the train station in Chicago?
Image credit: Jeramey Jannene
Link to image attribution
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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