1map logoGo to main page

Chicago, IL, USA to Poughkeepsie, NY, USA from $35: 7 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Chicago, United States of America
to
Poughkeepsie, United States of America

How to Get from Chicago to Poughkeepsie: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$35 by trainBest price
1143 kmDistance
5h 49m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Poughkeepsie with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Plane
Train
Average Duration
6h  36m
Estimated price
$146-608
Recommended
Company
Amtrak
Train
Average Duration
18h  43m
Estimated price
$35-270
Cheapest
route map
Distance: 1143 km
Duration: 5h 49m

See more options

Company
various
Plane
Train
Average Duration
6h  54m
Estimated price
$66-358
Company
various
Plane
Train
Average Duration
7h 
Estimated price
$78-494
Company
various
Plane
Drive
Average Duration
5h  49m
Estimated price
$174-640
Company
various
Plane
Bus
Train
Average Duration
8h  29m
Estimated price
$1460-1461
Company
various
Drive
Average Duration
13h  32m
Estimated price
$1462-1463
Browse car rentalsExplore flights

Traveling From Chicago to Poughkeepsie

Embark on a journey from the bustling city of Chicago to the tranquil charm of Poughkeepsie, where vibrant urban life meets serene riverside landscapes.

Best Neighbourhoods in Poughkeepsie

Poughkeepsie offers diverse neighborhoods, each with its own charm and attractions.

Downtown Poughkeepsie
• Trendy restaurants and cafes abound.
• Close to the Walkway Over the Hudson.
Historic District
• Beautiful 19th-century architecture.
• Home to local art galleries and boutiques.
Highland
• Scenic views of the Hudson River.
• Quaint shops and outdoor recreational spots.

Best Times To Visit Poughkeepsie's Attractions

Timing your visits can enhance your experience at Poughkeepsie's attractions.

Walkway Over the Hudson
Visit early in the morning during weekdays for peaceful views.
Vassar College
Explore the campus on weekends in spring for vibrant blooms.
The Bardavon 1869 Opera House
Attend weekday matinees for an intimate performance experience.

Poughkeepsie Weather: What to Expect Year-Round

Poughkeepsie experiences a humid continental climate, with cold winters and warm summers, making spring and fall the most pleasant times to visit. Weather conditions can affect outdoor activities, so packing layers and checking forecasts ahead of your trip is wise.

Dining Recommendations in Poughkeepsie

Try the farm-to-table offerings at The Roundhouse, where fresh local ingredients shine in dishes like the herb-crusted lamb or seasonal vegetable risotto, offering a stark contrast to Chicago’s deep-dish pizza scene. The rustic setting and emphasis on regional flavors provide a truly distinct dining atmosphere that enhances the experience of the Hudson Valley.

Chicago - Poughkeepsie operators

Explore transport companies operating between Chicago and Poughkeepsie, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Train
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Chicago Union Station to Poughkeepsie Amtrak Station

Average Duration
18h 43m
Estimated price
$35-270
Plane
Website
delta.com

Plane from Chicago Midway (MDW) to New York La Guardia (LGA)

Average Duration
2h 15m
Estimated price
$1466-1467

Plane from Chicago O'Hare (ORD) to New York La Guardia (LGA)

Average Duration
2h 9m
Estimated price
$6081-14660
Website
aa.com

Plane from Chicago O'Hare (ORD) to New York La Guardia (LGA)

Average Duration
2h 9m
Estimated price
$6081-14660

Plane from Chicago O'Hare (ORD) to Scranton/Wilkes-Barre (AVP)

Average Duration
1h 51m
Estimated price
$6081-6082
Website
united.com

Plane from Chicago O'Hare (ORD) to New York La Guardia (LGA)

Average Duration
2h 12m
Estimated price
$6081-14660

Plane from Chicago O'Hare (ORD) to Scranton/Wilkes-Barre (AVP)

Average Duration
1h 58m
Estimated price
$6081-6082
Website
southwest.com

Plane from Chicago Midway (MDW) to New York La Guardia (LGA)

Average Duration
2h 1m
Estimated price
$1464-1469

Plane from Chicago Midway (MDW) to Albany (ALB)

Average Duration
1h 52m
Estimated price
$6084-6085
Bus
Contact phone
+1 (914) 813-7777
Website
https://transportation.westchestergov.com/bee-line

Bus from Westchester Ave @ Paulding St to Tarrytown Railroad Station

Average Duration
40m
Estimated price
$350-350

Chicago to Poughkeepsie: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Poughkeepsie offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on an epic road trip from the vibrant city of Chicago to the charming town of Poughkeepsie. Traverse 818 miles of scenic landscapes and highways, immersing yourself in the beauty of the Midwest and East Coast. 💰 Enjoy the flexibility of cost options ranging from $140 to $220 for the journey by car, allowing you to plan according to your budget and preferences. Make pit stops along the way to explore hidden gems, taste local cuisines, and create lasting memories on this adventure-filled route. 🏞️ Arrive in Poughkeepsie after approximately 13 hours and 32 minutes of driving, feeling accomplished and rejuvenated by the unforgettable experiences and sights encountered during this exhilarating cross-country drive. Let the journey be as enriching as the destination itself.
Average price
$140 - $220
🌄 Enjoy approximately 18 hours and 43 minutes of relaxing travel through the beautiful landscapes of the Midwest and Northeast. With services operating daily, you can plan your trip to Poughkeepsie with ease. 💰 Ticket prices for the Chicago to Poughkeepsie train range from $35 to $270, providing budget-friendly options for all travelers. Sit back, relax, and experience the charm of train travel on this cross-country adventure.
Departure Point
Chicago Union Station
Arrival Point
Poughkeepsie Amtrak Station
🛫 Flying from Chicago to Poughkeepsie typically involves taking a flight from Chicago Midway Airport to New York La Guardia Airport. The quickest direct flight on this route takes approximately 2 hours.
Departure Point
Chicago Midway Airport
Arrival Point
New York La Guardia Airport

Frequently asked questions

Find out more about the route from Chicago to Poughkeepsie.

Or choose the category:
The distance between Chicago and Poughkeepsie is approximately 710 miles, or 818.4 miles by road. Travel times vary depending on the mode of transportation chosen. It takes approximately 18 hours and 43 minutes to reach Poughkeepsie from Chicago by train, 6 hours and 41 minutes by flying to New York La Guardia and then taking a train, 13 hours and 32 minutes by car, and 19 hours and 40 minutes by bus.
The most cost-effective option for traveling from Chicago to Poughkeepsie is by train, with prices ranging from $35 to $270. Although it takes longer, approximately 18 hours and 43 minutes, it is a more affordable choice. However, if time is a priority, the quickest way would be to fly from Chicago Midway to New York La Guardia and then take a train to Poughkeepsie. This option takes approximately 6 hours and 41 minutes but is more expensive, with prices ranging from $110 to $800.
The prices for a train journey between Chicago and Poughkeepsie range from $35 to $270, depending on the class of service and the time of booking. On the other hand, the prices for a bus trip between Poughkeepsie and Chicago can vary from $16 to $156, depending on the bus company, the type of seating, and the time of travel. It is advisable to book in advance and compare prices from different providers to get the best deal for your travel needs.
To get from Chicago to Poughkeepsie without using public transportation, your best option would be to drive. The driving distance between the two cities is approximately 818 miles, and it usually takes around 13 hours and 32 minutes to drive from Chicago to Poughkeepsie. You can expect to spend around $140 to $220 on gas and toll fees for this journey.
To travel from Chicago to Poughkeepsie without a car, the best option is to take the train. The journey takes approximately 18 hours and 43 minutes. Train tickets can range in price from $35 to $270, depending on the class and availability. Taking the train is a convenient and comfortable option for travelers looking to explore the scenic route between these two cities.
Yes, there is a direct train link between Chicago and Poughkeepsie. The train, operated by Amtrak, departs once daily from Chicago Union Station and arrives at Poughkeepsie Amtrak Station. The journey takes approximately 18 hours and 43 minutes. However, there is no direct bus service between the two cities. Passengers can take a bus from Chicago to Poughkeepsie with transfers, which can take approximately 19 hours and 40 minutes.
The flight between Chicago and Poughkeepsie typically takes about 2 hours on a direct flight. However, it is important to note that Poughkeepsie does not have its own airport, so travelers usually need to fly to a nearby airport such as New York La Guardia. The cost of the flight can vary depending on factors such as the airline, time of travel, and booking in advance. It is advisable to check with different airlines to get the most accurate and up-to-date pricing information.
Near Poughkeepsie there are plenty of options for accommodation with over 95 hotels available. Prices for these hotels start at $67 per night, offering a range of choices to suit different budgets. Whether you prefer luxury hotels or more budget-friendly options, there are plenty of options to choose from for your stay near Poughkeepsie.

Trips from Chicago

Trips to Peoria