Jun 18, 2026
Chicago road trip ideas: 5 adventures worth the drive
Every great road trip begins with a spark, and in the Midwest, that spark is Chicago. Spend time immersed in the city’s museums, lakefront, and neighborhoods, then set out to see what lies beyond. These five inspired routes all start with Chicago’s energy and unfold into memorable long‑weekend escapes. And each destination sits within an easy half‑day drive, offering history,...
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