How much does a train ticket from Poughkeepsie to Chicago cost?

The average train ticket price from Poughkeepsie to Chicago is $220. The best way to find 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 706 miles that separates the two cities.

How many daily trains 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 you 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.

What are the best sights and things to do in Chicago?

Once in Chicago, you can explore the city. The top sights and things to do are Museum of Contemporary Art, Willis Tower (Sears Tower), Chicago Shakespeare Theater on Navy Pier, Navy Pier, Lincoln Park Zoo.

Train Poughkeepsie to Chicago from $73 | Refundable Tickets

Next train departures

Next departures for Poughkeepsie to Chicago on November 20
Vehicle type	Departure time	Departure location	Trip duration	Arrival time	Arrival location	Recommended
Train	5:10pm	Poughkeepsie Station	18h 2m	10:12am	Chicago (Union Station), IL	CheapestFastest
Train	5:10pm	Poughkeepsie Station	18h 2m	10:12am	Chicago (Union Station), IL	No tags
Train	3:44pm	Poughkeepsie Station	19h 28m	10:12am	Chicago (Union Station), IL	No tags
Train	3:44pm	Poughkeepsie Station	19h 28m	10:12am	Chicago (Union Station), IL	No tags

Last refresh of the prices: Yesterday at 6:56 AM EST.

Get from Poughkeepsie to Chicago

This route is served by train only

The journey takes about 19 hours 28 minutes and with fares starting at just $77, it presents an excellent value for a comfortable ride.

1train per day

19h 28mAverage Duration

704 milesDistance

103kgCO₂ emissions

Train Companies

Amtrak

4/55,594 reviews

Staff4.7

Timeliness3.8

Cleanliness4.6

Wifi3.6

Based on 5594 reviews, the company was rated 4.1 stars on Busbud. Travelers were especially satisfied with the seats and the ticket access but often complained with the wifi. Amtrak ticket prices on this trip start at $77

Train and bus companies in US:Amtrak, Trenitalia, Renfe, VIA Rail Canada, Amtrak Acela, NS Nederlandse Spoorwegen, Iryo

Frequently asked questions about traveling from Poughkeepsie to Chicago by train

How much does a train ticket from Poughkeepsie to Chicago cost?
How long is the train trip from Poughkeepsie to Chicago?
How many daily trains are there between Poughkeepsie and Chicago?
Which train companies travel from Poughkeepsie to Chicago?
What are the best sights and things to do in Chicago?

Find cheapest prices for trains

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

Best price found

11/18

$126

11/19

$126

Today

$182

11/21

$265

11/22

$126

11/23

$126

11/24

$152

11/25

$105

The cheapest trip from Poughkeepsie to Chicago was searched and found on Nov 25, 2025 with a price of $105

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 $105 to $980 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 $105 which is on 2025-11-25.