Day 1: Chicago IL to Frankfort KY
Postcard from Frankfort, Kentucky.
Last year Route 66 started with tornadoes and flooding so today’s ride, mostly under torrential rain and thunderstorms, felt like a piece of cake really.
The first part of today’s 414 miles was on the highway to make up for the time I lost, stuck in traffic while leaving Chicagoland (note to self: that’s why you don’t own a car and don’t want to).
From Indianapolis onwards it was only minor, empty interstates and beautiful green country roads. Took me more than expected but I was rewarded by a pinky-ish sky while approaching Lexington.
Fried chicken and corn pudding + bourbon tasting to end the day in style. Can’t get more Kentucky than this can it?
Driving from Chicago to Frankfort Cheat Sheet
Accommodation in Frankfort:
- Bluegrass Inn, 635 Versailles Rd, Frankfort, KY 40601
Where to eat and what to see between Chicago IL and Frankfort KY
- Indianapolis Motor Speedway, 4790 W 16th St, Indianapolis, IN 46222 I grew up in Monza home of the Italian Formula 1 Grand Prix so it felt natural and required to stop here.
- Merrick Inn Restaurant, 1074 Merrick Dr, Lexington, KY 40502. The restaurant was full so I had to sit at the bar (which is my favorite way to eat here in the US. For once I had no doubts about what to eat: I had to have a Fried Chicken (I mean: when in Kentucky…). It was delicious.
- Bourbon On Main, 103 W Main St, Frankfort, KY 40601. Good for a little bourbon tasting before bed. Fun story: I didn’t want to drink and drive so I took an Uber from the Motel to the Bourbon tasting location. On the way back I called Uber again and… it was the same driver: the ONLY uber driver in Frankfort!
Driving from Chicago IL to Frankfort KY FAQ
From Chicago to Frankfort there are about 350 miles. My itinerary was 414 miles long due to some detours.
Going on a straight line without stopping anywhere it might take as little as 5 hours. My route took a lot more cause of the traffic leaving Chicago and cause I stopped in a few places, including spending a couple of hours for dinner before getting to the motel.
The Kentucky countryside is very, very nice and probably the highlight of a road trip from Chicago to Frankfort.
In Indianapolis the Indianapolis Motor Speedway, once in Kentucky a visit to Lexington is recommended but the most beautiful part if the countryside.
It really depends on the season but probably a midsize is the best choice. Since the weather was horrific, I was very happy with the uber-reliable Volvo I picked up at O’Hare!
Photos taken from Chicago, IL to Frankfort, KY
My itinerary on a road trip from Chicago to Key West
- Chicago to Key West – Main article
- Day 1: Chicago to Frankfort
- Day 2 and 3: Frankfort to Asheville
- Day 4 and 5: Asheville to Charleston
- Day 6: Charleston to Savannah
- Day 7: Savannah to Daytona Beach
- Day 8: Daytona Beach to Florida City
- Day 9: Florida City to Key West
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