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 | ||||
| Train | Poughkeepsie Station | Chicago (Union Station), IL | No tags |
Last refresh of the prices: Last Thursday at 6:37 PM EST.
Get from Poughkeepsie to Chicago
The journey takes about 18 hours 2 minutes, and with fares starting at just R 1 255, it presents an excellent value for a comfortable ride.
Train Companies
Based on 5750 reviews, the company was rated 4.1 stars on Busbud. Travellers were especially satisfied with the seats and the ticket access but often complained about the Wi-Fi. Amtrak ticket prices on this trip start at R 1 255
Frequently asked questions about travelling from Poughkeepsie to Chicago by train
Please note that timetables, routes, or operator details shown here may be updated or differ at the time of your trip.
How much is the train ticket from Poughkeepsie to Chicago?
The cheapest train tickets from Poughkeepsie to Chicago start from R 1 255. The average price for this train route is around R 3 724. Busbud recommends booking your tickets in advance for a better chance to secure the lowest possible price.
How long is the train journey from Poughkeepsie to Chicago?
The average train journey time from Poughkeepsie to Chicago is 18h 2m, covering a distance of 1136 km. The quickest train can get you there in 18h 2m and is operated by Amtrak.
Which train operators serve the Poughkeepsie to Chicago route?
Several major train operators run on this route, with 1 trains available per day.
What are the earliest and latest departure times for the train from Poughkeepsie to Chicago?
The earliest train from Poughkeepsie to Chicago departs at 15:44. And the latest train departs at 17:10.
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 24 Jan 2026 with a price of R 1 716To 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 1 716 to R 33 023 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 2 059, which is on 2026-01-27.
