The cheapest and fastest trains from Williamsburg, VA to Chicago, IL
Cheapest price
$359
Average price
$359
Fastest journey
1 d 2 h 25 m
Average duration
1 d 2 h 25 m
Trains per day
1
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 $359 if you buy it on the day, but the cheapest tickets can be found for only $359.
Of the 1 trains that leave Williamsburg, VA for Chicago, IL on Wed, May 13, 1 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Wed, May 13 the direct trains cover the 1066 km distance in an average of 1 d 2 h 25 m but if you time it right, some trains will get you there in just 1 d 2 h 25 m .
On Wed, May 13 the slowest trains will take 1 d 2 h 25 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.
11:20 AM26h25Williamsburg, VA1:45 PMChicago, IL$3591One-way0 transfers
11:20 AM26h25Williamsburg, VA1:45 PMChicago, IL$3591One-way0 transfers
Travel Information
Compare train, bus, and flight for Williamsburg, VA to Chicago, IL
Omio recommends booking the train as it is the most popular option from Williamsburg, VA to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $116. For those with little time consider booking a flight which can get you there in 4h 53m. The ticket price range depends on the travel mode: a bus costs an average of $116, and a train costs an average of $204.
Distance: 662 miles (1066 km)
Compare train with
Most popular Train | Bus | Flight | Driving |
|---|---|---|---|
$344 Average price | $150 Average price Cheapest | $287 Average price | $166 Average price (fuel + tolls) |
23h 13m Average total duration 22h 43m Onboard + 30m Additional time* | 25h 55m Average total duration 25h 25m Onboard + 30m Additional time* | 7h 53m Average total duration Fastest 4h 53m Onboard + 3h 0m Additional time* | 12h 43m Average total duration (door-to-door) |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Williamsburg, VA to Chicago, IL:
A bus is $136 (€109) less than a flight for this route with tickets for a flight from Williamsburg, VA to Chicago, IL costing on average $287 (€230).
A bus is $194 (€155) less than a train for this route with tickets for a train from Williamsburg, VA to Chicago, IL costing on average $344 (€275).
Other travel options to Chicago, IL take longer:
Train takes on average 22h 43m.
Bus takes on average 25h 25m.
Tickets start at around $344 (€275) compared to roughly $166 (€133) in fuel and tolls — a saving of about $-177.93 (€-142.42). The journey takes 22h 43m versus 12h 43m 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
Williamsburg, VA to Chicago, IL train times
The table below shows live departures for Williamsburg, VA to Chicago, IL trains for tomorrow, Wednesday, May 13. You can also manually refresh the results below to see updated train journeys.
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
![]() | 11:20 AM Williamsburg, VA | 26h25 | 1:45 PM 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 Williamsburg, VA 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.
May 13
May 14
May 15
May 16
May 17
May 18
May 19
Journey information
Overview: Train from Williamsburg, VA to Chicago, IL
Trains from Williamsburg, VA to Chicago, IL run on average 2 times per day, taking around 22h 43m. Cheap train tickets for this journey start at $204 (€164) but you can travel from only $116 (€93) 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 26h 25m.
Distance 662 miles (1066 km) |
Average train duration 22h 43m |
Cheapest ticket price $204 (€164) |
Trains per day 2 |
Fastest train 26h 25m |
First train 6:01 AM |
Last train 6:40 PM |
Cheapest Month Feb |
Cheapest Day Sun |
High Season Apr - Jun |
Low Season Jul - Sep |
Train companies: Amtrak from Williamsburg, VA to Chicago, IL trainsAmtrak trains will get you between Williamsburg, VA and Chicago, IL from $116 (€93). With over 1000 travel companies on Omio, you can find the best train times and tickets for your trip.
Amtrak
FAQs: Trains from Williamsburg, VA to Chicago, IL
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.

popular train stations
Popular train stations from Williamsburg, VA to Chicago, IL
- 6:00 AM - 10:00 PM Monday - Sunday
- Free
- Parking is available adjacent to the station with designated areas for short-term and long-term parking.
- Second Street Bistro
- Blue Talon Bistro
- Outside the main entrance.
- Ramps.
- $0.50
- Williamsburg Lodge
- Williamsburg Inn
- Colonial Houses
- Located in the main hall
- Located in the main hall
- Free
- Hall 1: main entrance, ticket office, and waiting area
- Hall 2: access to platforms and bus connections
- Bus: Williamsburg Area Transit Authority (WATA) routes
- Amtrak: Northeast Regional service
- 5:00 AM - 12:00 AM Monday - Sunday
- Free
- 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.
- The Chicago Firehouse Restaurant
- Lou Mitchell's
- Outside the main entrance.
- Elevators, ramps, restrooms.
- $1
- The Kimpton Gray Hotel
- JW Marriott Chicago
- W Chicago - City Center
- Located in the main hall
- Located in the main hall
- Avis
- Budget
- Enterprise
- Located in the main hall
- Free
- Hall 1: main entrance, Amtrak services
- Hall 2: Metra services
- Hall 3: food court and retail shops
- Bus: Several lines available
- CTA: Blue Line, Pink Line
More options for your journey from Williamsburg, VA to Chicago, IL
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