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

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

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$35 by trainBest price

1143 kmDistance

6h 35m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Poughkeepsie to Chicago 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.

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Traveling From Poughkeepsie to Chicago

Your journey from Poughkeepsie, with its serene riverside views, to the vibrant urban energy of Chicago, offers an exciting contrast between tranquil landscapes and a bustling cityscape.

Best Neighbourhoods in Chicago

Chicago boasts diverse neighborhoods, each with its own character and charm.

Wicker Park

• Trendy cafes and boutiques abound.

• Vibrant nightlife scene is popular.

Lincoln Park

• Offers beautiful parks and waterfront views.

• Home to the renowned Lincoln Park Zoo.

Hyde Park

• Rich in arts and culture attractions.

• Site of the prestigious University of Chicago.

Best Times To Visit Chicago's Attractions

Planning your visit to Chicago can enhance your experience at its top attractions.

Millennium Park

Visit early mornings or weekdays to enjoy the art without crowds.

The Art Institute of Chicago

Opt for late afternoons on weekdays for a quieter experience.

Navy Pier

Mornings are ideal to beat the rush and enjoy the waterfront.

Chicago Weather: What to Expect Year-Round

Chicago experiences a diverse climate with hot summers and cold winters, making spring and fall the best times to visit for mild temperatures. Weather conditions can significantly influence your travel plans, from outdoor events in comfortable months to cozy indoor activities during the chilly season.

Dining Recommendation in Chicago

Deep-dish pizza at Lou Malnati's is a must-try, showcasing Chicago's famous take on pizza that is a hearty contrast to the lighter fare often found in Poughkeepsie. The lively atmosphere and emphasis on local ingredients in Chicago's dining scene provide a unique culinary experience that celebrates bold flavors and community.

Poughkeepsie - Chicago operators

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

Train Show train routes

Contact phone

+1 800-872-7245

Website

https://www.amtrak.com/home.html

Train from Poughkeepsie Amtrak Station to Chicago Union Station

Average Duration

18h 2m

Estimated price

$35-270

Train from Poughkeepsie Amtrak Station to Albany-Rensselaer Amtrak Station

Average Duration

1h 5m

Estimated price

$2709-1010

Train from Milwaukee to Chicago Union Station

Average Duration

1h 29m

Estimated price

$1018-1019

Contact phone

877.690.5114

Website

https://new.mta.info/agency/metro-north-railroad

Train from Poughkeepsie to Grand Central Terminal

Average Duration

1h 53m

Estimated price

$35-357

Train from Poughkeepsie to Tarrytown

Average Duration

1h 9m

Estimated price

$2704-2705

Plane Show flights

Website

delta.com

Plane from New York La Guardia to Chicago Midway

Average Duration

5h 5m

Estimated price

$1167-1168

Plane from New York La Guardia to Chicago O'Hare

Average Duration

2h 48m

Estimated price

$1169-6970

Website

southwest.com

Plane from New York La Guardia to Chicago Midway

Average Duration

2h 31m

Estimated price

$1165-352

Plane from Albany to Chicago Midway

Average Duration

2h 17m

Estimated price

$1167-353

Website

aa.com

Plane from New York La Guardia to Chicago O'Hare

Average Duration

2h 46m

Estimated price

$1167-350

Plane from White Plains to Chicago O'Hare

Average Duration

2h 40m

Estimated price

$1167-350

Website

united.com

Plane from New York La Guardia to Chicago O'Hare

Average Duration

2h 46m

Estimated price

$1165-6976

Drive

Drive from Poughkeepsie to Chicago

Average Duration

13h 31m

Estimated price

$1163-1164

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

Traveling between Poughkeepsie and Chicago 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 a scenic road trip from Poughkeepsie to Chicago covering a distance of 818 miles. Buckle up for a journey that will take approximately 13 hours and 31 minutes of driving time. 💰 The cost of traveling by car from Poughkeepsie to Chicago ranges between $140 to $220, offering budget-friendly options for those looking to explore the Midwest. Enjoy the flexibility and affordability of a road trip compared to other modes of transportation.

Average price

$140 - $220

🌆 The journey spans approximately 18 hours and 2 minutes, allowing travelers to relax and take in the changing landscapes along the way. With services operating daily, passengers can choose a departure time that suits their schedule. 🎟️ Ticket prices for the Poughkeepsie to Chicago train range from $35 to $270, providing options for various budgets. Whether you're visiting for business or pleasure, a train ride offers a comfortable and enjoyable travel experience between these two vibrant cities.

Departure Point

Poughkeepsie Amtrak Station

Arrival Point

Chicago Union Station

🛫 Flying from Poughkeepsie to Chicago is efficient with a quick 2-hour and 25-minute direct flight from New York La Guardia Airport to Chicago Midway Airport. Delta and Southwest Airlines conveniently operate this route.

Departure Point

New York La Guardia Airport

Arrival Point

Chicago Midway Airport

Frequently asked questions

Find out more about the route from Poughkeepsie to Chicago.

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The distance between Poughkeepsie and Chicago is 710 miles. If you choose to travel by train, it takes approximately 18 hours and 2 minutes to reach Chicago from Poughkeepsie. Another option is to take a train to New York La Guardia and then fly to Chicago Midway, which takes about 6 hours and 24 minutes. If you prefer to drive, it takes around 13 hours and 31 minutes to reach Poughkeepsie from Chicago by car. Taking a bus can also be an option, but it typically takes around 18 hours and 23 minutes to reach Chicago from Poughkeepsie.

The most cost-effective option for traveling from Poughkeepsie to Chicago is by train, which costs between $35 and $270 and takes approximately 18 hours and 2 minutes. However, if time efficiency is a priority, the quickest option is to take a train to New York La Guardia and then fly to Chicago Midway. This option costs between $100 and $700 and takes around 6 hours and 24 minutes. Ultimately, the choice between cost-effectiveness and time efficiency depends on individual preferences and priorities.

When traveling from Poughkeepsie to Chicago the prices for a train ticket range from $35 to $270. On the other hand, the prices for a bus ticket between Chicago and Poughkeepsie vary from $18 to $151. It is advisable to check with the specific train or bus carrier for the most accurate and up-to-date pricing information.

To travel from Poughkeepsie to Chicago without using public transportation, you can opt for a road trip. The distance between the two cities is approximately 818 miles, and it takes about 13 hours and 31 minutes to drive the entire way. The cost of the trip by car varies from $140 to $220, depending on factors such as gas prices and tolls.

The best way to travel from Poughkeepsie to Chicago without a car is by train. The train journey takes approximately 18 hours and 2 minutes. The cost of the train ticket ranges from $35 to $270, depending on the class and time of travel. This option provides a comfortable and convenient mode of transportation for those who prefer not to drive.

Yes, there is a direct train link between Poughkeepsie and Chicago. The Amtrak train service operates once daily and the journey takes approximately 18 hours and 2 minutes. However, there is no direct bus service between the two cities. Those traveling by bus would need to make transfers and the journey, including transfers, takes approximately 18 hours and 23 minutes.

The flight from Poughkeepsie to Chicago typically takes 2 hours and 15 minutes. This is based on the quickest direct flight from New York La Guardia Airport to Chicago Midway Airport. The cost of the flight will vary depending on various factors such as the airline, time of booking, and availability, but on average, it can range from $150 to $300 per person. It's always recommended to check with different airlines and compare prices to get the best deal for your travel.

There are plenty of options for accommodation near Chicago with over 1116 hotels to choose from. Prices for hotels start at $58 per night, offering a range of budget-friendly to luxurious options. It is recommended to research different areas of the city, such as downtown, Magnificent Mile, or near popular attractions, to find the best hotel that fits your preferences and budget.

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

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

Compare Train, Bus, Flight, and Driving Options

See more options

Traveling From Poughkeepsie to Chicago

Best Neighbourhoods in Chicago

Best Times To Visit Chicago's Attractions

Chicago Weather: What to Expect Year-Round

Dining Recommendation in Chicago

Poughkeepsie - Chicago operators

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

Frequently asked questions

Trips from Poughkeepsie

Trips to Chicago

Popular routes