Orland Park to Winona: Road Trip Guide & Distance

How far is Orland Park from Winona?

The distance from Orland Park to Winona is 254.4 miles (409.4 km) as the crow flies. Winona is located NW of Orland Park. By car, the driving distance is approximately 318 miles, taking about 6h 24min. A direct flight would take roughly 1h 1min. Both are located in United States — Orland Park 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 Orland Park and Winona. The driving distance is estimated from straight-line distance with a road-factor model, so confirm the route in your navigation app. Fuel, flight, bus, and train values are planning estimates and can change by date, provider, road closures, and border rules.