Labor Day road trip

Chicago to Sister Bay for Labor Day

Distance

250 mi

Driving

4.5 hrs + traffic

Halfway

Milwaukee

The next Labor Day lands on Monday, September 6, 2027. On I-94, I-43 and WI-57, the heaviest traffic usually hits the Friday before and the Monday afternoon return. Coming home Tuesday morning instead of Monday afternoon saves hours in traffic.

Book the halfway night early

Milwaukee sits about 82 miles from Chicago and 168 miles from Sister Bay. Holiday weekends sell out the rooms near the highway first.

• Stays in Milwaukee
• Stays in Sister Bay

Along the way

• Milwaukee's lakefront
• Lambeau Field in Green Bay
• Peninsula State Park

Full drive guide for this route