Day 1: Chicago IL to Frankfort KY
![Chicago to Key West - Day 1: Chicago IL to Frankfort KY](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort-922x1024.jpg)
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?
![Chicago to Key West - Day 1: Chicago IL to Frankfort KY](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_1-922x1024.jpg)
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!
![Indianapolis Motor Speedway](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_2-925x1024.jpg)
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
![Road trip Chicago to Frankfort: country roads](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_4-922x1024.jpg)
![Road trip Chicago to Frankfort: sheep](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_3-925x1024.jpg)
![Chicago IL to Frankfort KY road-trip](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_5-922x1024.jpg)
![Chicago IL to Frankfort KY Road trip: bourbon tasting in Kentucky](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_chicago_to_frankfort_6-922x1024.jpg)
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
![Biscuit Head, Asheville breakfast](https://www.youarenotatree.net/wp-content/uploads/2023/08/roadtrip_frankfort_to_asheville_8.jpg)