Road Trip Midwest

Chicago to Florida Drive- We help you map out the best stops, activities, and hotels on your Chicago to Florida road trip with family.

Are you ready for the most epic road trip from Chicago to Yellowstone? We have a full itinerary for you, including great stops along the way.

Fields of corn, soybeans, small towns, and water towers line the 300-mile stretch of land, and short detours off of the main highway take families through cities with small populations and plenty of local charm.