- Must visit
Art Institute Of Chicago
One of the world’s leading art museums, famous for Impressionist masterpieces, American art, and major special exhibitions.
2,000+ travel companies
2,000+ travel companies
Scan to get our free app
Use our app to get live travel updates and book mobile tickets for trains, buses, flights, and ferries.
App Store
4.942K ratings
Google Play
4.6136K reviews
The cheapest and fastest trains from Poughkeepsie, NY to Chicago, IL
Showing times and prices for Jun 17
Cheapest price
$206
Average price
$228
Fastest journey
18 h 2 m
Average duration
18 h 2 m
Trains per day
2
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 $228 if you buy it on the day, but the cheapest tickets can be found for only $206.
Fast trains
Of the 2 trains that leave Poughkeepsie, NY for Chicago, IL on Wed, Jun 17, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, Jun 17 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 Wed, Jun 17 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.
10:10 PM18h02Poughkeepsie, NY4:12 PMChicago, IL$2061One-way0 transfers- 9:10 PM18h02Poughkeepsie, NY3:12 PMChicago, IL$2501One-way0 transfers
- 10:10 PM18h02Poughkeepsie, NY4:12 PMChicago, IL$2061One-way0 transfers
- 9:10 PM18h02Poughkeepsie, NY3:12 PMChicago, IL$2501One-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 $63. 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 $63, and a train costs an average of $140.
Distance: 706 miles (1137 km)
Compare train with
Most popular Train | Flight | Bus | Driving |
|---|---|---|---|
$259 Average price | $171 Average price Cheapest | $198 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 $171 (€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 $198 (€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 $259 (€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 $259 (€210) compared to roughly $166 (€135) in fuel and tolls — a saving of about $-92.55 (€-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, Tuesday, June 16. You can also manually refresh the results below to see updated train journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 5:10 PM Poughkeepsie, NY | 17h02 | 10:12 AM 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.
Wed
Jun 17
Jun 17
Thu
Jun 18
Jun 18
Fri
Jun 19
Jun 19
Sat
Jun 20
Jun 20
Sun
Jun 21
Jun 21
Mon
Jun 22
Jun 22
Tue
Jun 23
Jun 23
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 $140 (€114) but you can travel from only $63 (€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 $63 (€51)
Distance 706 miles (1137 km) |
Average train duration 18h 3m |
Cheapest ticket price $140 (€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 $63 (€51)
Train companies: Amtrak from Poughkeepsie, NY to Chicago, IL trainsAmtrak trains will get you between Poughkeepsie, NY and Chicago, IL from $63 (€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
$140 (€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
Things to do in Chicago
Discover the best of Chicago — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago trip today.
- Must visit
Field Museum
Major natural history museum known for Sue the T. rex, ancient cultures, and large family-friendly science exhibits.
- Must visit
Museum Of Science And Industry
Large hands-on science museum in Hyde Park with a U-505 submarine, aviation exhibits, and immersive interactive displays.
- Must visit
Millennium Park
Chicago’s signature public space, home to Cloud Gate and major events, with strong appeal for first-time visitors and photographers.
- Must visit
Chicago Riverwalk
Scenic pedestrian route along the Chicago River, popular for architecture views, strolling, and social-media-friendly city scenes.
- Must visit
Magnificent Mile
Famous stretch of North Michigan Avenue known for landmark architecture, flagship stores, and busy big-city energy.
Deep-Dish Pizza
Chicago’s iconic thick-crust pizza baked in a deep pan, layered with cheese, toppings, and chunky tomato sauce. It is one of the city’s most famous comfort foods.
Chicago-Style Hot Dog
An all-beef hot dog on a poppy seed bun topped with mustard, onions, neon relish, tomato, pickle spear, sport peppers, and celery salt. It is a classic local street food.
Italian Beef Sandwich
Thinly sliced roast beef piled onto an Italian roll, often dipped in seasoned jus and topped with sweet peppers or giardiniera. It is a defining Chicago sandwich.
Gene & Georgetti
A historic old-school steakhouse serving steaks, chops, and classic Italian-American dishes in a traditional setting.
Alinea
Chicago’s internationally acclaimed fine-dining restaurant known for highly inventive tasting menus and exceptional service.
Lou Malnati's Pizzeria
A long-established Chicago favorite known for buttery deep-dish pizza and a casual, family-friendly atmosphere.
United States Dollar
Moderate by U.S. big-city standards. Hotels can be pricey downtown, but food and transit offer good value.
Average meal costs
- Budget
- USD 10-18 for fast food or casual takeout.
- Mid-range
- USD 25-45 per person at a mid-range restaurant.
- Fine dining
- USD 80+ per person before drinks and tip.
- Coffee
- USD 4-7 for a regular café coffee.
Tipping culture
Tip 18-20% at sit-down restaurants; 20%+ for great service. USD 1-2 per drink at bars, round up or 10-15% for taxis, and USD 1-2 per bag for hotel staff.
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 $140 (€114), while the average price is around $259 (€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 $63 (€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
Poughkeepsie
Chicago
The major train station for departures in Poughkeepsie is Poughkeepsie Station. Find all the information you need to know about services, amenities and connections at Poughkeepsie Station for your trip from Poughkeepsie to Chicago.
Amenities at train station
Wifi
Lockers
Parking
Dining
Taxis
Accessibility
WC
Hotel
Lost and Found Office
Ticket Office
Bike Parking
Information Desk
Luggage Cartsinformation
Ticket Office Hours
- 6:00 AM - 10:00 PM Monday - Sunday
Distance to city center
1 km
Number of platforms
2Wifi
- Free
Parking
- Parking is available 7 days a week. Access via Main Street.
Dining
- River Station Restaurant
- Brasserie 292
Taxis
- Outside the main entrance.
Accessibility
- Elevators, ramps.
WC
- $0.50
Hotel
- Residence Inn Poughkeepsie
- Courtyard by Marriott Poughkeepsie
- Holiday Inn Express Poughkeepsie
Lost and Found Office
- Located in the main hall
Information Desk
- Located in the main hall
Luggage Carts
- Free
Station Plan
- Hall 1: main entrance, ticket office, and waiting area
- Hall 2: access to platforms
Public transit options for Poughkeepsie Station
- Metro-North Railroad: Hudson Line
- Bus: Dutchess County Public Transit
The major train station for arrivals in Chicago is Union Station. Find all the information you need to know about services, amenities and connections at Union Station for your journey to Chicago from Poughkeepsie.
Amenities at train station
WifiLockersParkingDining
ATMTaxisAccessibilityWCHotel
LoungeLost and Found OfficeTicket OfficeBike Parking
Car RentalInformation DeskLuggage Cartsinformation
Ticket Office Hours
- 5:00 AM - 12:00 AM Monday - Sunday
Distance to city center
3 kmNumber of platforms
24Wifi
- Free
Parking
- 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.
Dining
- The Chicago Firehouse Restaurant
- Lou Mitchell's
Taxis
- Outside the main entrance.
Accessibility
- Elevators, ramps, restrooms.
WC
- $1
Hotel
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
Lounge
- Located in the main hall
Lost and Found Office
- Located in the main hall
Car Rental
- Avis
- Budget
- Enterprise
Information Desk
- Located in the main hall
Luggage Carts
- Free
Station Plan
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
Public transit options for Union Station
- Bus: Several lines available
- CTA: Blue Line, Pink Line
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
The Omio App Makes Travel Planning Easy
We’ll get you where you want to go. From live train updates to mobile tickets, our innovative app is the ideal way to plan and keep track of your travel.
