The cheapest and fastest trains from Poughkeepsie, NY to Chicago, IL
Cheapest price
$243
Average price
$243
Fastest journey
17 h 2 m
Average duration
17 h 2 m
Trains per day
1
Distance
1137 km
The best way to find a cheap train ticket from Poughkeepsie, NY to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Poughkeepsie, NY to Chicago, IL will cost around $243 if you buy it on the day, but the cheapest tickets can be found for only $243.
Of the 1 trains that leave Poughkeepsie, NY for Chicago, IL on Thu, Nov 06, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Thu, Nov 06 the direct trains cover the 1137 km distance in an average of 17 h 2 m but if you time it right, some trains will get you there in just 17 h 2 m .
On Thu, Nov 06 the slowest trains will take 17 h 2 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 Poughkeepsie, NY to Chicago, IL
Omio recommends booking the train as it is the most popular option from Poughkeepsie, NY to Chicago, IL among Omio's users. If you are prioritising price take the flight with prices starting from €23. For those with little time consider booking a flight which can get you there in 2h 37m. The ticket price range depends on the travel mode: a flight costs an average of €23, and a bus costs an average of €195.
Distance: 706 miles (1137 km)
Compare train with
Most popular Train | Flight | Bus |
|---|---|---|
€175 Average price | €117 Average price Cheapest | €201 Average price |
18h 2m Average total duration 17h 32m Onboard + 30m Additional time* | 5h 37m Average total duration Fastest 2h 37m Onboard + 3h 0m Additional time* | 25h 26m Average total duration 24h 56m Onboard + 30m Additional time* |
Direct Options | Direct Options | Direct Options |
Live departures
Poughkeepsie, NY to Chicago, IL train times
The table below shows live departures for Poughkeepsie, NY to Chicago, IL trains for today, Wednesday, November 5. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 9:10 PM Poughkeepsie, NY | 18h02 | 3:12 PM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Compare prices and tickets Poughkeepsie, NY to Chicago, IL 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.
Nov 06
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Nov 12
Journey information
Overview: Train from Poughkeepsie, NY to Chicago, IL
Distance 706 miles (1137 km) |
Average train duration 17h 32m |
Cheapest ticket price $140 (€115) |
Trains per day 2 |
Direct trains 1 |
Fastest train 18h 2m |
First train 15:44 |
Last train 21:30 |
Train companies: Amtrak from Poughkeepsie, NY to Chicago, IL trainsAmtrak trains will get you between Poughkeepsie, NY and Chicago, IL from $29 (€23). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Poughkeepsie, NY to Chicago, IL

popular train stations
Popular train stations from Poughkeepsie, NY to Chicago, IL
- 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
- 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
More options for your journey from Poughkeepsie, NY to Chicago, IL
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