Labor Day trips from Chicago

Where can you actually afford to go for Labor Day (2026-09-04–2026-09-07) from Chicago? Ask Weekender and get ranked destinations with numbers that bind.

Popular from Chicago

• Charleston, SC
• Denver, CO
• Indianapolis, IN
• Lake Geneva, WI
• Madison, WI
• Milwaukee, WI
• New Orleans, LA
• San Juan, PR
• Saugatuck, MI
• Seattle, WA