The cheapest and fastest trains from Chicago, IL to Poughkeepsie, NY
Cheapest price
$250
Average price
$287
Fastest journey
19 h 43 m
Average duration
19 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 $287 if you buy it on the day, but the cheapest tickets can be found for only $250.
Of the 2 trains that leave Chicago, IL for Poughkeepsie, NY on Tue, Dec 23, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Tue, Dec 23 the direct trains cover the 1137 km distance in an average of 19 h 43 m but if you time it right, some trains will get you there in just 19 h 43 m .
On Tue, Dec 23 the slowest trains will take 19 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.




Travel Information
Compare train, bus, and flight for Chicago, IL to Poughkeepsie, NY
Omio recommends booking the train as it is the most popular option from Chicago, IL to Poughkeepsie, NY among Omio's users. If you are prioritising price take the flight with prices starting from €179. For those with little time consider booking a flight which can get you there in 6h 0m. The ticket price range depends on the travel mode: a flight costs an average of €179, and a train costs an average of €202.
Distance: 706 miles (1137 km)
Compare train with
Most popular Train | Bus | Flight |
|---|---|---|
€230 Average price | €200 Average price | €194 Average price Cheapest |
19h 6m Average total duration 18h 36m Onboard + 30m Additional time* | 38h 5m Average total duration 37h 35m Onboard + 30m Additional time* | 9h 0m Average total duration Fastest 6h 0m Onboard + 3h 0m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Chicago, IL to Poughkeepsie, NY train times
The table below shows live departures for Chicago, IL to Poughkeepsie, NY trains for today, Monday, December 22. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:30 PM Chicago, IL | 19h43 | 5:13 PM Poughkeepsie, NY | 1 transfer | |
![]() | 9:30 PM Chicago, IL | 19h43 | 5:13 PM Poughkeepsie, NY | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Chicago, IL to Poughkeepsie, NY by train, bus, or flight
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Dec 23
Dec 24
Dec 25
Dec 26
Dec 27
Dec 28
Dec 29
Why should you book Chicago to Poughkeepsie trains with Omio?
Amtrak operates all train services from Chicago to Poughkeepsie. Omio is the only official third party seller for Amtrak tickets.
Why book with Omio vs Amtrak?
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare Amtrak with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Chicago to Poughkeepsie.
Why book with Omio over Trainline and Rail Europe?
- Official reseller: Amtrak tickets can only be bought on Omio or Amtrak's website as Omio is the only official third party seller for Amtrak tickets. Trainline, RailEurope, and Rail.Ninja do not sell Amtrak tickets as they are not official sellers.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Chicago to Poughkeepsie.
Journey information
Overview: Train from Chicago, IL to Poughkeepsie, NY
Trains from Chicago, IL to Poughkeepsie, NY run on average 4 times per day, taking around 18h 36m. Cheap train tickets for this journey start at $252 (€202) but you can travel from only $224 (€179) 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 19h 43m.
Distance 706 miles (1137 km) |
Average train duration 18h 36m |
Cheapest ticket price $252 (€202) |
Trains per day 4 |
Direct trains 1 |
Fastest train 19h 43m |
First train 15:44 |
Last train 21:30 |
Train companies: Amtrak from Chicago, IL to Poughkeepsie, NY trainsAmtrak trains will get you between Chicago, IL and Poughkeepsie, NY from $224 (€179). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Chicago, IL to Poughkeepsie, NY
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.

popular train stations
Popular train stations from Chicago, IL to Poughkeepsie, NY
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- The car park is open 7 days a week from 5:00 a.m. to 12:00 a.m. Departures can be made outside of opening hours. Access via Canal Street.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
- 6:00 AM - 10:00 PM Monday - Sunday
- Free
- Parking is available 7 days a week. Access via Main Street.
- River Station Restaurant
- Brasserie 292
- Outside the main entrance.
- Elevators, ramps.
- $0.50
- Residence Inn Poughkeepsie
- Courtyard by Marriott Poughkeepsie
- Holiday Inn Express Poughkeepsie
- Located in the main hall
- Located in the main hall
- Free
- Hall 1: main entrance, ticket office, and waiting area
- Hall 2: access to platforms
- Metro-North Railroad: Hudson Line
- Bus: Dutchess County Public Transit
Most popular train connections from Chicago, IL
More options for your journey from Chicago, IL to Poughkeepsie, NY
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