Chicago to Winona: Road Trip Guide & Distance
How far is Chicago from Winona?
The distance from Chicago to Winona is 252.2 miles (405.8 km) as the crow flies. Winona is located NW of Chicago. By car, the driving distance is approximately 305.8 miles, taking about 5h 44min. A direct flight would take roughly 1h 0min. Both are located in United States — Chicago in Illinois and Winona in Minnesota.
For a drive of this length, it's recommended to plan at least one quick rest stop to stretch your legs and grab a coffee. Since you'll be heading mostly West, pack a good pair of sunglasses if you plan to drive during the late afternoon to avoid the harsh sun glare.
Coordinates come from public place data for Chicago and Winona. The driving distance uses an OSRM road-route result when route data is available. Fuel, flight, bus, and train values are planning estimates and can change by date, provider, road closures, and border rules.
How to Get from Chicago to Winona
Suggested Stops Between Chicago & Winona
- 1122 mi
- 237 mi
- 380 mi
- 427 mi
- 535 mi
Quick Facts
Did You Know?
- At walking speed (3 mph), it would take about 84 hours of non-stop walking
- By bicycle at 12 mph, the journey would take roughly 21 hours
- You could travel this distance about 98.8 times to circle the Earth's equator