- Must visit
Hudson River Maritime Museum
Riverfront museum with Hudson River maritime exhibits, historic vessels, and boatbuilding programs that connect visitors to Kingston’s working waterfront.
Trains from Chicago, IL to Kingston, NY run on average 8 times per day, taking around 17h 48m. Cheap train tickets for this journey start at $165 (€139) but you can travel from only $113 (€95) by flight.
There are 2 trains per day. The fastest train covers the 701 miles (1129 km) distance in 17h 5m.
Distance 701 miles (1129 km) |
Average train duration 17h 48m |
Cheapest ticket price $165 (€139) |
Trains per day 8 |
Direct trains 2 |
Fastest train 17h 5m |
High Season Jul - Sep |
Low Season Apr - Jun |
Discover the best of Kingston, NY — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Kingston, NY trip today.
Riverfront museum with Hudson River maritime exhibits, historic vessels, and boatbuilding programs that connect visitors to Kingston’s working waterfront.
Artist-built environment featuring mosaics, sculptures, and painted structures. Visits are by guided tour, offering a distinctive local art experience.
Contemporary art center in Midtown presenting rotating exhibitions, performances, and community-focused programs in a restored industrial building.
Kingston’s historic waterfront district with brick streets, galleries, boat traffic, and a walkable mix of maritime heritage and local shops.
Uptown district centered on a historic stockade area with old stone buildings, small museums, and one of the city’s best walking environments.
Linear rail trail for walking and cycling, linking Kingston neighborhoods with public art, bridges, and easy Hudson Valley scenery.
Cider doughnuts are a Hudson Valley fall staple, made with apple cider and warm spices. They are closely tied to the region's orchards and harvest season.
Apple pie is a classic regional dessert in the Hudson Valley, showcasing local orchard fruit. Kingston is a strong base for tasting traditional apple desserts.
Maple Syrup is a traditional Catskills and Hudson Valley product, used on pancakes and in sweets. It reflects the area's spring sugaring heritage.
Lively downtown restaurant known for creative American comfort food, cocktails, and a stylish but relaxed setting.
Upscale yet approachable spot serving seasonal New American dishes and drinks in a polished historic space in Uptown Kingston.
Popular casual venue for wood-fired pizza, pasta, and Italian-American fare with a friendly neighborhood atmosphere.
Moderate for a small US city. Hotels can be limited, dining is mid-priced, and local transport options are modest, so visitors often rely on cars or taxis.
Tip 15-20% in restaurants, more for great service. Round up or tip 10% for taxis. Small tips are appreciated at cafes, but not always expected.
Find answers to the most common questions about traveling from Chicago, IL to Kingston, NY 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 Kingston, NY, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Kingston, NY trains use the Union Station to Poughkeepsie Station station pair. Use this guide to compare Chicago, IL and Kingston, NY train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Union Station is 3 km from Chicago city centre. Public transport options include:
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 options include: The Chicago Firehouse Restaurant, Lou Mitchell's
Free. ATMs are available in the train station.
Ticket office support is available at Union Station. Information desks are located in the main hall.
Luggage storage is available at Union Station. Lost and found is available at the station.
Available at Union Station: Parking, Taxis, WC.
Available at Union Station: Bike Parking, Car Rental.
Accessibility facilities are available at Union Station: Elevators, ramps, restrooms.
Nearby hotels include The Kimpton Gray Hotel, JW Marriott Chicago, W Chicago - City Center.
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