6 days in Kentucky Itinerary

6 days in Kentucky Itinerary

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Route & dates

6 days in Kentucky Itinerary

Start: Chicago
Fly:  3​h 45​min
1
Louisville
— 3 nights
Drive:  1​h 30​min
2
Lexington
— 2 nights
Fly:  3​h 15​min
End: Chicago

3
nights
Louisville

Louisville ©
Kentucky’s largest city, Louisville, is best known as the home of the Kentucky Derby.
Explore Louisville's surroundings by going to National Corvette Museum (in Bowling Green), Mammoth Cave (in Mammoth Cave National Park) and Onyx Cave (in Cave City). Next up on the itinerary: Head underground at Louisville Mega Cavern, see the interesting displays at Louisville Slugger Museum & Factory, snap pictures at The Big Four Bridge, and try to win big at Churchill Downs.

To see traveler tips, where to stay, ratings, and other tourist information, go to the Louisville day trip site .

Chicago to Louisville is an approximately 4-hour flight. You can also drive; or do a combination of flight and bus. Traveling from Chicago to Louisville, you'll lose 1 hour due to the time zone difference. When traveling from Chicago in October, plan for a bit warmer days in Louisville, with highs around 71°F, while nights are about the same with lows around 50°F. Cap off your sightseeing on the 13th (Sun) early enough to go by car to Lexington.

Things to do in Louisville

Museums Parks Nature

Side Trips

Onyx Cave, Mammoth Cave, National Corvette Museum
Highlights from your plan
Mammoth Cave ©
Mammoth Cave
National Corvette Museum ©
National Corvette Museum
Churchill Downs ©
Churchill Downs

2
nights
Lexington

Lexington
Known internationally as the "Horse Capital of the World," Lexington boasts a thriving economy resting largely on its thoroughbred racehorse industry.
On the 14th (Mon), indulge your thirst for a good beer at Lexington Brewing & Distilling Co., then brush up on your knowledge of spirits at Buffalo Trace Distillery, and then try your luck at Keeneland. Here are some ideas for day two: brush up on your knowledge of spirits at Barrel House Distillery, sample the tasty concoctions at Woodford Reserve Distillery, and then see the interesting displays at Ark Encounter.

To see maps, photos, reviews, and more tourist information, you can read our Lexington road trip planner .

Traveling by car from Louisville to Lexington takes 1.5 hours. Alternatively, you can take a bus. In October, daytime highs in Lexington are 70°F, while nighttime lows are 49°F. Finish your sightseeing early on the 15th (Tue) to allow enough time to travel back home.

Things to do in Lexington

Breweries & Distilleries Casinos Fun & Games

Side Trips

Woodford Reserve Distillery, Ark Encounter, Buffalo Trace Distillery
Highlights from your plan
Ark Encounter
Ark Encounter
Keeneland ©
Keeneland
Buffalo Trace Distillery ©
Buffalo Trace Distillery

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