The cheapest way to get from Chicago to Kentucky costs only $65, and the quickest way takes just 3½ hours. Find the travel option that best suits you.

Fly one-way from Chicago (Midway) to Louisville starting at $49. Bundle your Southwest Airlines® flight with a hotel or rental car booking and find even more savings.

The cheapest ticket to Kentucky from Chicago found in the last 72 hours was $36 one-way, and $57 round-trip. The most popular route is from Chicago to Lexington , and the cheapest round …

The trip from Chicago to Louisville takes as short as 7 hours 15 minutes and could cost as little as $43.98. The first bus departs at 6:10 am and the last bus departs at 10:00 pm . Greyhound …

Find United Airlines cheap flights from Chicago to Lexington. Enjoy a Chicago to Lexington modern flight experience in premium cabins with Wi-Fi.

Fly from Chicago on United Airlines, Southwest, American Airlines and more. Search for Louisville flights on KAYAK now to find the best deal. Find flights to Louisville from $49.

Find airfare and ticket deals for cheap flights from Chicago to Kentucky. Search flight deals from various travel partners with one click at $42.

Chicago (ORD) to Lexington (LEX) flight schedule. The monthly calendar shows every direct flight departure from Chicago O Hare International (ORD) with all airlines. Click on a date to see a …

Find flights to Kentucky from $41. Fly from Chicago O'Hare Airport on Frontier, American Airlines, United Airlines and more. Search for Kentucky flights on KAYAK now to find the best deal.

There are 9 ways to get from Kentucky to Chicago by plane, bus (Amtrak), bus, train, or car. Select an option below to see step-by-step directions and to compare ticket prices and travel …