- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Cheapest price on Oct 04
€164
Average ticket price on Oct 04
€164
Fastest journey on Oct 04
1 d 4 h 5 m
Average journey duration on Oct 04
1 d 4 h 5 m
Trains on Oct 04
2
Distance
1066 km
The best way to find a cheap train ticket from Williamsburg, VA 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 Williamsburg, VA to Chicago, IL will cost around €164 if you buy it on the day, but the cheapest tickets can be found for only €164.
On Sun, Oct 04, we found 2 trains from Williamsburg, VA to Chicago, IL, including 2 direct services.
On Sun, Oct 04 the direct trains cover the 1066 km distance in an average of 1 d 4 h 5 m but if you time it right, some trains will get you there in just 1 d 4 h 5 m .
On Sun, Oct 04 the slowest trains will take 1 d 4 h 5 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.




Trains from Williamsburg, VA to Chicago, IL run on average 1 times per day, taking around 21h 32m. Cheap train tickets for this journey start at €171 but you can travel from only €96 by bus.
The earliest train runs at 06:01, the last at 18:40. The fastest train covers the 662 miles (1066 km) distance in 21h 32m.
Distance 662 miles (1066 km) |
Average train duration 21h 32m |
Cheapest ticket price €171 |
Trains per day 1 |
Fastest train 21h 32m |
First train 6:01 AM |
Last train 6:40 PM |
Cheapest Month Feb |
Cheapest Day Sun |
High Season Apr - Jun |
Low Season Oct - Dec |
The table below shows live departures for Williamsburg, VA to Chicago, IL trains for tomorrow, Sunday, October 4. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 11:20 AM Williamsburg, VA | 28h05 | 3:25 PM Chicago, IL | 0 transfersDirect | |
![]() | 12:20 PM Williamsburg, VA | 28h05 | 4:25 PM Chicago, IL | 0 transfersDirect | |
This is the last train of the day. | |||||
Find all the dates and times for this journey
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
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.
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 is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
Find answers to the most common questions about traveling from Williamsburg, VA 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.

Most Williamsburg, VA to Chicago, IL trains use the Williamsburg Transportation Center to Union Station station pair. Use this guide to compare Williamsburg, VA and Chicago, IL train stations on this route, check city-centre transport, alongside checking practicalities like train station facilities and services.
Williamsburg Transportation Center 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 options include: Second Street Bistro, Blue Talon Bistro
Free.
Ticket office support is available at Williamsburg Transportation Center. Information desks are located in the main hall.
Luggage storage is available at Williamsburg Transportation Center. Lost and found is available at the station.
Available at Williamsburg Transportation Center: Parking, Taxis, WC.
Available at Williamsburg Transportation Center: Bike Parking.
Accessibility facilities are available at Williamsburg Transportation Center: Ramps.
Nearby hotels include Williamsburg Lodge, Williamsburg Inn, Colonial Houses.
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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