Next train departures
| Operated by | Vehicle type | Departure time | Departure location | Trip duration | Arrival time | Arrival location | Recommended | Price and booking link |
|---|---|---|---|---|---|---|---|---|
 | Train | Poughkeepsie Station | Chicago (Union Station), IL | CheapestFastest | ||||
| Train | Poughkeepsie Station | Chicago (Union Station), IL | No tags | ||||
| Train | Poughkeepsie Station | Chicago (Union Station), IL | No tags | ||||
| Train | Poughkeepsie Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Yesterday at 6:56 AM EST.
Get from Poughkeepsie to Chicago
The journey takes about 19 hours 28 minutes, and with fares starting at just R 1 355, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5594 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained with the Wi-Fi. Amtrak ticket prices on this trip start at R 1 355
Frequently asked questions about travelling from Poughkeepsie to Chicago by train
How much does a cheap train ticket from Poughkeepsie to Chicago cost?
The average train ticket price from Poughkeepsie to Chicago is R 3 875. The best way to find cheap train tickets from Poughkeepsie to Chicago is to book your tickets as early as possible. Prices tend to rise as your travel date approaches, so book in advance to secure the best prices!
How long is the train trip from Poughkeepsie to Chicago?
A train trip between Poughkeepsie and Chicago is around 19h 28m, although the fastest train will take about 18h 2m. This is the time it takes to travel the 1138 km that separates the two cities.
How many daily train are there between Poughkeepsie and Chicago?
The number of trains from Poughkeepsie to Chicago can differ depending on the day of the week. On average, there is 1. Some trains are direct while others have layovers. Simplify your train trip from Poughkeepsie to Chicago by comparing and selecting the train that fits your travel style and budget on Busbud.
Which train companies travel from Poughkeepsie to Chicago?
When taking the train from Poughkeepsie to Chicago, you can travel comfortably and safely with Amtrak.
Find cheapest prices for trains
Price is for a one-way ticket for one passenger and based on past searches.
The cheapest trip from Poughkeepsie to Chicago was searched and found on 25 Nov 2025 with a price of R 1 853To save money and be sure you have the best seat, it's a good idea to buy your train tickets from Poughkeepsie to Chicago as early as possible.
You can expect to pay from R 1 853 to R 17 292 for a train ticket from Poughkeepsie to Chicago based on the last 2 days. You can expect to find the cheapest price for the trip at R 1 853, which is on 2025-11-25.
