Chicago Day Trips

Discover exciting day trips from Chicago including heritage tours, scenic getaways, and city highlights. Perfect for a memorable day adventure!

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African American Heritage Tour of Chicago

This tour visits the homes of Louis Farrakhan, the former home of Elijah Muhammad and the former home of Muhammad Ali. We will pass by and take pictures at the

★ 4.4 (144)

From $125.00 USD

Chicago City's Iconic Sights and Suburb Gems Tour

This tour offers a refreshing blend of Chicago’s iconic sights and hidden suburban gems, giving travelers a unique perspective on the city's diverse culture, hi

From $299.00 USD

Chicago Private Tour to Lake Geneva and Anderson Japanese Gardens

Discover the natural beauty of Lake Geneva and the tranquil Anderson Japanese Gardens on this private 10‑hour getaway from Chicago. Begin your day with convenie

From $1,200.00 USD

Chicago to Mackinac Island Scenic Tour

Explore the charm of Mackinac Island on this delightful journey from Chicago. Experience a blend of history, culture, and stunning landscapes as you travel thro

From $685.00 USD

Chicago to Milwaukee Day Trip with Brewery Tour & City Highlights

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-Davids

★ 4.5 (12)

From $125.00 USD

Chicago VIP Private Tour

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighbor

From $499.00 USD

Chicago-Milwaukee Small Group Tour

Discover the charm of Milwaukee on a small group day trip from Chicago! Enjoy a guided city tour, explore iconic landmarks, and experience the legendary Miller

From $485.00 USD

Lake Geneva, Anderson Japanese Gardens 1 Day Tour From Chicago

Escape the city and discover the serene beauty of the Midwest on this full-day Lake Geneva and Anderson Japanese Gardens tour from Chicago. Start your journey w

From $133.00 USD