Chicago to Key West

Day 1: Chicago IL to Frankfort KY

Chicago to Key West - 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?


Chicago to Key West - Day 1: Chicago IL to Frankfort KY
Ready to start my road trip from Illinois to Florida. First leg: Chicago IL to Frankfort KY


Driving from Chicago to Frankfort Cheat Sheet

Accommodation in Frankfort:

Where to eat and what to see between Chicago IL and Frankfort KY

  • Indianapolis Motor Speedway4790 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
I grew up in Monza not too far from the Formula one racetrack so a stop at the Indianapolis Motor Speedway was a must.

Driving from Chicago IL to Frankfort KY FAQ

How many miles are from Chicago to Frankfort?

From Chicago to Frankfort there are about 350 miles. My itinerary was 414 miles long due to some detours.

How long does it take to drive from Chicago to Frankfort?

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.

What’s the best thing about driving from Chicago to Frankfort?

The Kentucky countryside is very, very nice and probably the highlight of a road trip from Chicago to Frankfort.

What are the major attractions along the way in 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.

What type of car is best to drive from Chicago to Frankfort?

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!

Can you drive an electric car from Chicago to Frankfort?

Yes you can. You just need a little bit of additional planning to find an EV charger. Before leaving for Frankfort, make sure your EV is enough charged. The city of Chicago has 794 public charging station ports.
Here some EV charging station available in Chicago:
– EVgo Charging Station,3 W Chicago Ave, Chicago, IL 60654 Phone: (877) 494-3833
– Tesla Supercharger, 225 N Columbus Dr, Chicago, IL 60601 (At Radisson Hotel)
– ChargePoint Charging Station, 545 N McClurg Ct, Chicago, IL 60611. Phone: (888) 758-4389



Photos taken from Chicago, IL to Frankfort, KY

Road trip Chicago to Frankfort: country roads
Road trip Chicago to Frankfort: country roads in Indiana

Road trip Chicago to Frankfort: sheep
Road trip Chicago to Frankfort: making friends along the way

Chicago IL to Frankfort KY road-trip
Fried chicken in Kentucky is a must have, right?

Chicago IL to Frankfort KY Road trip: bourbon tasting in Kentucky
Ending the first day of this road trip with a bourbon tasting in Frankfort, Kentucky

Leave a Reply

Your email address will not be published. Required fields are marked *