How long is the drive to Chicago?

The drive takes approximately 11.5 hours of pure driving time.

Amtrak offers service from Charlottesville to Chicago, but you must drive to Charlottesville first.

What is the best route?

I-64 West to I-70 West to I-65 North is the most direct and common route.

Yes, there are toll roads in the Chicago area; be prepared for costs.

You would need to drive to Richmond or Charlottesville to catch a flight to Chicago.

Chicago

Driving

Shipman to Chicago

Updated: 28 May 2026

The journey from Shipman to Chicago is an 1,100-kilometer drive that takes you through the heart of the Midwest. You will head north and west, primarily using I-70 and I-65 to reach Chicago. This drive typically takes 11 to 12 hours, passing through several major cities. It is a popular route for those traveling from Virginia to the major urban center of Chicago.

Total Distance: 1,100 km driving distance; 950 km straight-line air distance.

Fastest Way

Driving is the most practical method, taking about 11.5 hours of pure drive time.

Cheapest Way

Driving is the most cost-effective way to transport a group to Chicago.

Compare Shipman to Chicago Routes

Driving

Direct

Duration

11 hours 30 mins

Avg Price

$130-$170 in fuel

Operator

Personal Vehicle

Route

I-64 W to I-70 W to I-65 N through Indianapolis and Chicago.

Plan for heavy traffic when entering the Chicago metropolitan area.

Travel Tips

Traffic Alerts
Chicago traffic is notoriously heavy; use a GPS app for real-time updates.
Parking
Parking in downtown Chicago is very expensive; consider using public transit or parking garages outside the city center.
Rest Stops
Indianapolis is a great place to stop for food and rest halfway through the trip.
Fueling
Gas prices are generally competitive along the I-65 corridor.
Weather
Be prepared for cold and snowy conditions in the winter months.

Safety Tips

Driver Fatigue
Take regular breaks to stay alert on the long drive.
Speeding
Speed limits are strictly enforced on I-65, particularly in small towns.
Weather
Be prepared for sudden weather changes in the Midwest, which can affect road conditions.
Vehicle Prep
Check your tire pressure and fluid levels before leaving for this long trip.