Cheap train tickets from Poughkeepsie to Chicago

Find and compare the best ground travel options in one place.

Trip Summary

There are usually 2 daily train trips available from Poughkeepsie to Chicago. Traveling by train from Poughkeepsie to Chicago usually takes 18 hours and 45 minutes, but the fastest Amtrak Lake Shore Limited train can make the trip in 18 hours and 2 minutes.

Distance: 706 mi (1136 km)
Fastest train: 18h 2m
Lowest price: SEK 2,180.87
Trains per day: 1
Most frequent service: Amtrak
Train lines: 2

Millions of travelers trust Wanderu every year to get:

Lowest Prices

We find the cheapest bus & train tickets, so you can wander for less.

Best Travel Options

We partner with 500+ carriers to bring you the most bus & train options.

Quick & Easy Booking

Book trips quickly with a simple, hassle-free checkout – online & on our app.

Fast Customer Support

We don’t monkey around. We respond within minutes to help you out.

See what travelers are saying about Wanderu:

Download our free app!

Find, compare & book buses and trains on the go with the Wanderu app.

4.8 Rating

5k Reviews

4.5 Rating

4.8k Reviews

Poughkeepsie to Chicago Train Schedule

No preview is currently available. Please try another date or search the full schedule.

There are several train options that can take you from Poughkeepsie to Chicago:

See more details

What is the price of a train ticket from Poughkeepsie to Chicago?

In the last month, the average price of a train ticket from Poughkeepsie to Chicago was SEK 2,476. Considering the distance between Poughkeepsie and Chicago, tickets on this route are relatively expensive. The further in advance you book your travels, the more likely it is you can find tickets at this price or lower.

Average train ticket prices from Poughkeepsie to Chicago by travel date

Over the next 30 days, a one-way train trip from Poughkeepsie to Chicago will cost between SEK 1,680 and SEK 3,311. Book in advance to secure the best price in the next few weeks.

Average train ticket prices from Poughkeepsie to Chicago by month

Ticket prices for the train from Poughkeepsie to Chicago often fluctuate based on the time of year. For the best prices on this route, book in February when the average ticket price is only SEK 1,837. If you're thinking of traveling from Poughkeepsie to Chicago during August, keep in mind that train ticket prices may be higher than usual, with an average price of SEK 3,301 during this time of year. The best way to score a cheap deal, even in August, is to book your trip well in advance.

Prices as travel date approaches

You can score the best price on a train ticket from Poughkeepsie to Chicago by booking on Wanderu in advance. Tickets are nearly always cheaper the further in advance you purchase them.

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	SEK 2,502.10
Amtrak Lake Shore Limited	1	18h 2m	SEK 4,210.45

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 is 1 Amtrak train from Poughkeepsie to Chicago every day, as well as 1 trip on the weekends, with prices starting from SEK 1,493.21.
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 Union Station in Chicago. The route takes about 18 hours and 2 minutes and ticket prices start at SEK 1,306.56.

Frequently asked questions about traveling by train from Poughkeepsie to Chicago

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.

Trains per day

Direct trains

The distance between Poughkeepsie and Chicago is approximately 706 miles. The average train journey between these two cities takes 18 hours and 45 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.

Distance (mi)

706

Distance (km)

1136

The earliest train departs Poughkeepsie at 3:44 PM while the last train of the day leaves at 5:10 PM. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

First train

3:44pm

Last train

5:10pm

Trains from Poughkeepsie to Chicago are the most crowded on Thursday. 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 Sunday instead, as it tends to be the least crowded day of the week.

Busiest

Thursday

Least crowded

Sunday

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 Bardavon 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?

Main arrival station: Union Station

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:

Union Station

Need a return trip from Chicago to Poughkeepsie?

Search Train Tickets

Plan your next adventure

Wanderu is the simplest way to book bus and train travel.

With just a quick search on Wanderu, you can compare bus and train schedules and prices from hundreds of travel companies in one convenient place to find the trip that works best for you. Wanderu’s simple checkout process makes it easy to book cheap bus and train tickets hassle-free. Most importantly, as Wanderu is an official partner of all leading bus and train companies, we always have the best bus and train deals out there.