Top Day Trips from Chicago (Updated November 2026)

Escape Chicago for a day and experience Milwaukee’s culture, food, and legendary beer scene. This curated day trip includes highlights such as the Harley-Davidson Museum,...
$125

Explore Chicago’s amazing architecture from the unique perspective of elevated trains and station platforms. Learn the history behind the famous "L" system and hear how...
$35

Embark on the adventure of a lifetime! Step aboard the iconic California-Chicago Train Expedition as we whisk you away on a journey that combines the...
$5

