Discover the top five best places to visit on a road trip between Chicago, Illinois, and Lexington, Kentucky. Experience art, natural history, sports cars, and more.

Planning a trip from Chicago to Lexington? This comprehensive guide breaks down the costs and distances of different transportation options, including driving, train, bus, and flying. Discover the most affordable and efficient route for your journey.

Embark on a fun road trip from Chicago to Lexington, exploring different routes, distances, and estimated driving times. Discover charming towns, scenic landscapes, and recommended stops along the way. Find the perfect adventure from the Windy City to Horse Country!