Is there a direct train?

Yes, the Amtrak Empire Builder runs directly from St. Paul to Chicago.

How long is the drive?

The drive is approximately 6 hours under normal traffic conditions.

What is the best highway?

I-94 East is the most direct and efficient highway route.

Yes, expect tolls on the Illinois portion of the I-94 corridor.

Yes, flights are available from MSP to ORD, taking about 90 minutes.

Woodbury

Chicago

Train Driving

Woodbury to Chicago

Updated: 28 May 2026

The journey from Woodbury to Chicago spans approximately 410 miles across the heart of the Midwest. You can drive via I-94 East, passing through Eau Claire and Madison before entering Illinois. Alternatively, the Amtrak Empire Builder departs from St. Paul Union Depot, offering a scenic rail connection. The drive typically takes 6 hours, while the train journey lasts about 7 hours and 30 minutes. This route is a major artery connecting the Twin Cities metropolitan area to the third-largest city in the United States.

Total Distance: 660 km driving distance; 560 km straight-line air distance.

Fastest Way

Driving is the fastest method, taking approximately 6 hours depending on traffic in Chicago.

Cheapest Way

Driving is generally the cheapest for groups of two or more, costing roughly $75 in fuel.

Compare Woodbury to Chicago Routes

	Train Direct	Driving Direct
Duration	7 hours 30 mins	6 hours
Avg Price	$50-$150	$60-$90 in fuel
Operator	Amtrak Empire Builder	Personal Vehicle
Route	St. Paul Union Depot to Chicago Union Station	I-94 East through Wisconsin
Tip	Book business class for extra legroom and power outlets.	Expect heavy traffic near Milwaukee during rush hour.

Travel Tips

Train Booking
Book your Amtrak tickets at least three weeks in advance to secure lower fares.
Traffic Timing
Avoid entering Chicago via I-90/94 between 7 AM and 9 AM to bypass severe congestion.
Parking
Use apps like SpotHero to find discounted parking garages in downtown Chicago.
Public Transit
Purchase a Ventra card upon arrival to easily navigate the CTA trains and buses.
Weather Prep
Chicago is known as the Windy City; always carry a windbreaker regardless of the season.

Safety Tips

Vehicle Security
Never leave valuables visible in your car when parking in downtown lots.
Public Transit Awareness
Stay alert on the CTA Red Line, especially during late-night hours.
Pedestrian Safety
Use designated crosswalks, as Chicago traffic can be aggressive toward pedestrians.
Emergency Contacts
Save the local non-emergency police number for the district you are visiting.