- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
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The cheapest and fastest trains from Poughkeepsie, NY to Chicago, IL
Showing times and prices for Aug 01
Cheapest price
$248
Average price
$248
Fastest journey
18 h 2 m
Average duration
18 h 2 m
Trains per day
1
Distance
1137 km
Cheap tickets
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 $248 if you buy it on the day, but the cheapest tickets can be found for only $248.
Fast trains
Of the 1 trains that leave Poughkeepsie, NY for Chicago, IL on Sat, Aug 01, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Sat, Aug 01 the direct trains cover the 1137 km distance in an average of 18 h 2 m but if you time it right, some trains will get you there in just 18 h 2 m .
On Sat, Aug 01 the slowest trains will take 18 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.
9:10 PM18h02Poughkeepsie, NY3:12 PMChicago, IL$2481One-way0 transfers
- 9:10 PM18h02Poughkeepsie, NY3:12 PMChicago, IL$2481One-way0 transfers
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 $62. 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 $62, and a train costs an average of $139.
Distance: 706 miles (1137 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$258 Average price | $170 Average price Cheapest | $196 Average price | $166 Average price (fuel + tolls) |
18h 33m Average total duration 18h 3m Onboard + 30m Additional time* | 5h 37m Average total duration Fastest 2h 37m Onboard + 3h 0m Additional time* | 26h 6m Average total duration 25h 36m Onboard + 30m Additional time* | 12h 28m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
The cheapest way to travel from Poughkeepsie, NY to Chicago, IL is a flight with an average price of $170 (€138).
This is compared to other travel options from Poughkeepsie, NY to Chicago, IL:
A flight is $27 (€22) less than a bus for this route with tickets for a bus from Poughkeepsie, NY to Chicago, IL costing on average $196 (€160).
A flight is $88 (€71) less than a train for this route with tickets for a train from Poughkeepsie, NY to Chicago, IL costing on average $258 (€210).
The fastest way to travel from Poughkeepsie, NY to Chicago, IL is by flight with an average journey time of 2h 37m.
Other travel options to Chicago, IL take longer:
Train takes on average 18h 3m.
Bus takes on average 25h 36m.
It's helpful to compare your options as there are 3 ways to travel between Poughkeepsie, NY and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Poughkeepsie, NY to Chicago, IL among Omio's users.
Take the train. It's the cheaper option, and the extra time on board is usually more relaxing than driving it.
Tickets start at around $258 (€210) compared to roughly $166 (€135) in fuel and tolls — a saving of about $-92.02 (€-74.97). The journey takes 18h 3m versus 12h 28m by car, so you'll arrive a bit later, but you can work, read, or sleep along the way rather than spending the time behind the wheel. You'll also save the hassle of parking at the other end.
Driving is worth it if you're on a tight schedule, travelling as a group, or want to stop somewhere en route.
Live departures
Poughkeepsie, NY to Chicago, IL train times
The table below shows live departures for Poughkeepsie, NY to Chicago, IL trains for today, Friday, July 31. You can also manually refresh the results below to see updated train journeys.
Last updated at
| 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.
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Journey information
Overview: Train from Poughkeepsie, NY to Chicago, IL
USAUSA
Trains from Poughkeepsie, NY to Chicago, IL run on average 2 times per day, taking around 18h 3m. Cheap train tickets for this journey start at $139 (€114) but you can travel from only $62 (€51) 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 18h 2m.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $62 (€51)
Distance 706 miles (1137 km) |
Average train duration 18h 3m |
Cheapest ticket price $139 (€114) |
Trains per day 2 |
Direct trains 1 |
Fastest train 18h 2m |
First train 3:44 PM |
Last train 9:30 PM |
Cheapest Month Aug |
Cheapest Day Sat |
High Season Jan - Mar |
Low Season Oct - Dec |
Best time to book 77 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Cheapest alternative travel mode
Flight from $62 (€51)
Train companies: Amtrak from Poughkeepsie, NY to Chicago, IL trainsAmtrak trains will get you between Poughkeepsie, NY and Chicago, IL from $62 (€51). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
About
Amtrak is the main passenger train operator in the United States, providing medium- and long-distance intercity services across 46 states and three Canadian provinces. Operating over 300 trains daily and serving more than 500 destinations, Amtrak connects cities and regions nationwide through routes such as the high-speed Acela in the Northeast Corridor, the scenic Coast Starlight along the West Coast, and the Empire Builder linking Chicago to the Midwest and the Pacific Northwest. Other notable services include the Northeast Regional, Keystone Service, and the unique Auto Train, which allows passengers to bring their cars onboard. Amtrak offers a variety of classes to suit different budgets and travel needs, including Coach, Business, First Class, and Sleeper Class with options like Roomettes, Bedrooms, and Bedroom Suites for overnight journeys. Ticket types include Saver, Value, Flexible, Business, and Premium. Onboard amenities vary by service but may include comfortable seating, Wi-Fi, power outlets, dining options, and lounge access on select trains. Popular routes include Washington, D.C.–Boston, San Diego–San Luis Obispo, San Jose–Sacramento, and Chicago–Seattle.
Luggage & cancellation policy
Average Duration
18h 2m
Cheapest Price
$139 (€114)
Amtrak frequency
2 a day
Luggage included
2 personal items and 2 carry-on bags included free
Luggage storage
Overhead racks, under seats, and designated luggage areas at end of cars
Cancellation Policy
Cancellation policies depend on ticket type and timing
Refund
Full refund if train is canceled by Amtrak
Amenities on board the train
Wifi
Food sold onboard
Café car with snacks, beverages, and light meals. Long-distance trains have full-service dining cars
Seat reservation
Included in ticket price for Business and First Class. Optional fee for Coach Class
Toilets
USB plugs
Accessibility
Wheelchair spaces, accessible restrooms, Red Cap assistance service, accessible platforms and stations
Pets
Small pets under 20 pounds allowed for $26 fee. Must be in carrier. Service animals travel free
Quiet zone
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
FAQs: Trains from Poughkeepsie, NY to Chicago, IL
Find answers to the most common questions about traveling from Poughkeepsie, NY to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.
Train ticket prices from Poughkeepsie, NY to Chicago, IL can vary. The cheapest ticket starts at $139 (€114), while the average price is around $258 (€210).
The train from Poughkeepsie, NY to Chicago, IL takes 18h 2m and runs 2 per day.
The first train from Poughkeepsie, NY to Chicago, IL leaves at 3:44 PM.
The distance by train from Poughkeepsie, NY to Chicago, IL is 706 miles (1137 km).
The last train from Poughkeepsie, NY to Chicago, IL leaves at 9:30 PM.
There is no high speed train available from Poughkeepsie, NY to Chicago, IL.
Yes, there is a direct train from Poughkeepsie, NY to Chicago, IL. This service operates 1 times per day, provided by Amtrak.
Unfortunately, there is no night train available from Poughkeepsie, NY to Chicago, IL.
The train station in Poughkeepsie, NY that goes to Chicago, IL is Poughkeepsie Station, Poughkeepsie, NY, which connects to Chicago Union Station, Chicago, IL.
The cheapest way to get from Poughkeepsie, NY to Chicago, IL is by flight, with a cost of around $62 (€51).
The train journey from Poughkeepsie, NY to Chicago, IL offers scenic views, particularly during the initial stretch along the Hudson River, where travelers can enjoy picturesque landscapes and historic sites. As the route progresses, it transitions through the rolling hills of upstate New York and the rural expanses of the Midwest, providing varied and scenic vistas along the way.
A day trip from Poughkeepsie, NY to Chicago, IL is not feasible as the journey takes 18h 2m. The distance is 706 miles (1137 km) and there are 2 trains per day.
In Chicago, IL, you can explore the Museum of Science and Industry and its interactive exhibits, enjoy the vibrant neighborhoods like Wicker Park and Lincoln Park, take a river cruise to view iconic architecture, and attend a live performance at the historic Chicago Theatre. Visit Lincoln Park Zoo for a free and enjoyable day. For sights, don't miss Millennium Park with its modern art, the renowned Art Institute of Chicago, the entertainment hub of Navy Pier, panoramic views from Willis Tower Skydeck, and the fascinating exhibits at the Field Museum.
To fully experience Chicago, IL, plan for at least 3-4 days to visit key attractions such as Millennium Park, The Art Institute of Chicago, Navy Pier, and explore diverse neighborhoods.
Yes, you can take the train from Poughkeepsie, NY to Chicago, IL.
Since neither Poughkeepsie, NY nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
Popular day trips by train from Chicago, IL include Milwaukee, WI, South Bend, IN, New Buffalo, MI, Racine, WI, Elkhart, IN.
We recommend using the train as it is the most popular way to get from Poughkeepsie, NY to Chicago, IL among Omio's users.
Items not allowed on trains typically include hazardous materials such as explosives, flammable liquids, corrosive substances, and illegal drugs. Additionally, large or bulky items that may obstruct aisles or emergency exits, as well as pets without proper carriers, may be restricted. Specific prohibited items can vary by train operator and region, so please check the rules for your particular journey.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular train stations
Popular train stations from Poughkeepsie, NY to Chicago, IL
Most Poughkeepsie, NY to Chicago, IL trains use the Poughkeepsie Station to Union Station station pair. Use this guide to compare Poughkeepsie, NY and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Departure train stations in Poughkeepsie
Arrival train stations in Chicago
Which Poughkeepsie, NY station do trains to Chicago, IL leave from?
Trains from Poughkeepsie, NY to Chicago, IL leave from Poughkeepsie Station. The station is 1 miles (2 km) from Poughkeepsie, NY city centre at 41 Main Street, Poughkeepsie, NY 12601, USA.
Poughkeepsie Station41 Main Street, Poughkeepsie, NY 12601, USA1-800-USA-RAIL
City-centre transport
Getting to Poughkeepsie Station from Poughkeepsie city centre
Poughkeepsie Station is 1 km from Poughkeepsie city centre. Public transport options include:
BusRoute P · 15m · $2 · every ~1 min
Poughkeepsie Station train station facilities and services
Poughkeepsie Station has practical services for this route, including Wifi, Lockers, Parking, Dining, Taxis, Accessibility, WC, Hotel, Lost and Found Office, Ticket Office, Bike Parking, Information Desk, and Luggage Carts.
Food and drink
Food options include: River Station Restaurant, Brasserie 292
Wi-Fi and ATMs
Free.
Tickets and information
Ticket office support is available at Poughkeepsie Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Poughkeepsie Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Poughkeepsie Station: Parking, Taxis, WC.
Bike and car services
Available at Poughkeepsie Station: Bike Parking.
Accessibility
Accessibility facilities are available at Poughkeepsie Station: Elevators, ramps.
Shops, hotels and contact
Nearby hotels include Residence Inn Poughkeepsie, Courtyard by Marriott Poughkeepsie, Holiday Inn Express Poughkeepsie.
Which Chicago, IL station do trains from Poughkeepsie, NY arrive at?
Trains from Poughkeepsie, NY to Chicago, IL arrive at Union Station. Union Station is 1 miles (3 km) from Chicago, IL city centre.
Union Station225 South Canal Street, Chicago, IL 60606, USA+1 800-872-7245
City-centre transport
Getting to Union Station from Chicago city centre
Union Station is 3 km from Chicago city centre. Public transport options include:
Bus28, 151 · 7m · $4 · every ~13 min
Union Station train station facilities and services
Union Station has practical services for this route, including Wifi, Lockers, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Lounge, Lost and Found Office, Ticket Office, Bike Parking, Car Rental, Information Desk, and Luggage Carts.
Food and drink
Food options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Wi-Fi and ATMs
Free. ATMs are available in the train station.
Tickets and information
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage and lost property
Luggage storage is available at Union Station. Lost and found is available at the station.
Parking, taxis and toilets
Available at Union Station: Parking, Taxis, WC.
Bike and car services
Available at Union Station: Bike Parking, Car Rental.
Accessibility
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Shops, hotels and contact
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
Most popular train connections from Poughkeepsie, NY
More options for your journey from Poughkeepsie, NY to Chicago, IL
Here are some other resources that might have the information you need
Most popular trains to and from Chicago, IL and Poughkeepsie, NY
Most popular train connections to Chicago, IL
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