Train Poughkeepsie to Chicago from €66

Next train departures

Next departures from Poughkeepsie to Chicago on 20 March
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	CheapestFastest
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags

Next departures from Poughkeepsie to Chicago on 21 March
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	CheapestFastest
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags

Next departures from Poughkeepsie to Chicago on 23 March
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	CheapestFastest
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags

Next departures from Poughkeepsie to Chicago on 24 March
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	CheapestFastest
Train	17:10	Poughkeepsie Station	18h 2m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags
Train	15:44	Poughkeepsie Station	19h 28m	10:12	Chicago (Union Station), IL	No tags

Last refresh of the prices: Today at 07:43 EDT.

Find cheapest prices for trains

Price is for a one-way ticket for one passenger and based on past searches.

Best price found

17/03

€163

18/03

€196

Today

No data

20/03

€239

21/03

€196

22/03

€209

23/03

€163

24/03

€163

The cheapest trip from Poughkeepsie to Chicago was searched and found on 17 Mar 2026 with a price of €163

To 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 €163 to €1,813 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 €163, which is on 2026-03-23.