- Must visit
Franklin D. Roosevelt Presidential Library and Museum
Presidential library chronicling Franklin and Eleanor Roosevelt through exhibits, archives, and a nationally significant collection.
Cheapest price
$168
Average price
$184
Fastest journey
18 h 43 m
Average duration
18 h 43 m
Trains per day
2
Distance
1137 km
The best way to find a cheap train ticket from Chicago, IL to Poughkeepsie, NY 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 Poughkeepsie, NY will cost around $184 if you buy it on the day, but the cheapest tickets can be found for only $168.
Of the 2 trains that leave Chicago, IL for Poughkeepsie, NY on Thu, Aug 06, 2 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 1137 km distance in an average of 18 h 43 m but if you time it right, some trains will get you there in just 18 h 43 m .
On Thu, Aug 06 the slowest trains will take 18 h 43 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.




Trains from Chicago, IL to Poughkeepsie, NY run on average 3 times per day, taking around 18h 43m. Cheap train tickets for this journey start at $165 but you can travel from only $101 by flight.
There are 1 trains per day. The earliest train runs at 15:44, the last at 21:30. The fastest train covers the 706 miles (1137 km) distance in 18h 43m.
Distance 706 miles (1137 km) |
Average train duration 18h 43m |
Cheapest ticket price $165 |
Trains per day 3 |
Direct trains 1 |
Fastest train 18h 43m |
First train 3:44 PM |
Last train 9:30 PM |
Cheapest Month May |
Cheapest Day Tue |
High Season Jan - Mar |
Low Season Jul - Sep |
Best time to book 1 day |
The table below shows live departures for Chicago, IL to Poughkeepsie, NY trains for tomorrow, Wednesday, August 5. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 2:30 AM Chicago, IL | 18h43 | 9:13 PM Poughkeepsie, NY | 0 transfersDirect | |
![]() | 3:30 AM Chicago, IL | 18h43 | 10:13 PM Poughkeepsie, NY | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Discover the best of Poughkeepsie, NY — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Poughkeepsie, NY trip today.
Presidential library chronicling Franklin and Eleanor Roosevelt through exhibits, archives, and a nationally significant collection.
Leading contemporary art museum on Vassar’s campus, known for thought-provoking exhibitions and strong Hudson Valley cultural appeal.
Historic house museum and estate preserving the life of Samuel Morse, with river views, gardens, and guided interpretation.
Expansive riverfront park beneath the Walkway, popular for waterfront walks, events, and dramatic Hudson views.
Large urban park with trails, athletic fields, and quiet wooded sections, loved by locals for everyday recreation.
Scenic hilltop preserve with a short climb to a panoramic overlook of the Hudson Valley and surrounding highlands.
A classic Hudson Valley breakfast side made from local apples, slowly cooked into a chunky sauce. It reflects the region's long apple-growing tradition.
Cider made from Hudson Valley apples, served fresh or sparkling. The area is one of New York's historic cider regions, making it a local staple drink.
Tart made with local orchard apples in a flaky crust. It is a signature dessert across the Hudson Valley, especially during harvest season.
Refined New American restaurant known for seasonal Hudson Valley ingredients, polished service, and an intimate upscale setting in downtown Poughkeepsie.
Popular casual smokehouse serving barbecue, burgers, and comfort food in a lively, rustic space with a strong local following.
Established Italian restaurant known for pasta, seafood, and classic entrées in a warm, traditional dining room near the waterfront.
Moderate for the Hudson Valley: hotels often cost more than small-town stays, while dining is mid-priced and local transit is limited, so visitors may rely on taxis or rideshare.
Tip 18-20% in restaurants, about 15-20% for taxis, and $1-2 per drink or coffee in cafes if service is provided.
Find answers to the most common questions about traveling from Chicago, IL to Poughkeepsie, NY 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 Poughkeepsie, NY, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Poughkeepsie, NY trains use the Union Station to Poughkeepsie Station station pair. Use this guide to compare Chicago, IL and Poughkeepsie, NY train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
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.
Poughkeepsie Station is 1 km from Poughkeepsie city centre. Public transport options include:
Poughkeepsie Station has practical services for this route, including Wifi, Lockers, Parking, Dining, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Information Desk, and Luggage Carts.
Food options include: River Station Restaurant, Brasserie 292
Free.
Ticket office support is available at Poughkeepsie Station. Information desks are located in the main hall.
Luggage storage is available at Poughkeepsie Station. Lost and found is available at the station.
Available at Poughkeepsie Station: Parking, Taxis, WC.
Available at Poughkeepsie Station: Bike Parking.
Accessibility facilities are available at Poughkeepsie Station: Elevators, ramps.
Nearby hotels include Residence Inn Poughkeepsie, Courtyard by Marriott Poughkeepsie, Holiday Inn Express Poughkeepsie.
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