US Roadtrips

Chicago to Miami & Key West road trip

Chicago to Key West
Rainbow Row, in Charleston with its famous pastel colored houses

My Chicago to Key West Road Trip

With the Route 66 I drove the year before, still in my eyes, in 2022 I’ve decided to embark in another road trip, this time in a different direction: South. Actually: a road trip from Chicago to the southernmost city in the continental United States: Key West. If driving the historic Route 66 I’ve mainly stayed in small towns, driving every single day, this time the plan was different: I didn’t just want to drive but I wanted to stop in some cities some friends told me great things about. The roadtrip from Chicago to Key West took me through 7 different States: Illinois, Indiana, Kentucky, North and South Carolina, Georgia and, finally, Florida.

You can either click here to get to the daily posts with all sort on additional info about my trip – where I stayed, what I ate, what I saw – or here if you want to read all the daily postcards in one go.

Or just keep scrolling.



Planning a road-trip from Chicago to Key West

In order to avoid Florida’s hurricane season I’ve decided to take this road-trip in May. It ended up not being the best idea weather wise for the first part of the trip but all in all I think it was the right choice.

Planning the trip wasn’t complicated: after reading a couple of blogs and, most importantly, thanks to the priceless recommendations and tips of a special person, I already had a good idea of where I was going, what food I wanted to try, where I was stopping and about all the things I was looking forward to do.

I didn’t buy any map I’ve relied entirely on Google Map which aside from a couple of time on the Blue Ridge Mountains when I lost internet connection, has been uber-reliable.

How Long is a road trip from Chicago to Key West?

On a straight line driving on the I-65 S and I-75 S going from Chicago to Key West means driving for a bit more than 1,500 miles. My itinerary was much longer, 2,073 miles to be exact, due to a number of diversions along the route.

How many days does it takes to drive from Chicago to Key West?

Said that driving on the highways you can cover the distance from Illinois to Florida in a couple of days, it took me 9 days to get to Key West, stopping for a couple of nights in a couple of different places I didn’t just want to drive through.


Day 6: Charleston SC to Savannah GA
Beautiful houses in Savannah, easily one of my favorite small cities in America


My 9 days itinerary on a road trip from Chicago to Key West

Like the year before I picked up my car at O’Hare airport – cause it was cheaper than renting downtown – early in the morning and soon after I was on my way South. From there this was the itinerary (A description, map and general information are in each daily post)

What are the best cities to stop overnight when driving from Chicago to Key West?

My personal favorite were Asheville, Charleston and Savannah. The first is a super cool place with tons of amazing breweries (yes I like beer), great food and great vibes. Charleston has an amazing food scene and Savannah, well Savannah is just beautiful.

What are the most beautiful road you can drive in a road trip from Chicago to Miami?

Driving all the way from Chicago to Miami there are plenty of beautiful iconic road to drive. My favorite:

  • The Old Frankfort Pike from Frankfort toward Lexington.
  • The North Carolina section of the Blue Ridge Parkway
  • The Ashley River road in Charleston
  • Oak Avenue in the outskirt of Savannah
  • The road and the bridges connecting the Keys

Where do you stay when driving from Chicago to Key West?

Once again I tried to stay mostly in motels but in a couple of places such as Charleston where I wanted to try staying in one of those beautiful and colorful colonial homes


Having a refreshing moment in Key West at the end of my road trip from Chicago to Florida


How many miles do you need to drive every day and for how many hours?

My stubborn decision to avoid driving on the highways whenever possible and the weather being not always the best at least till South Carolina, meant that I was sitting on a car most of the day. Far the longest leg both in terms of miles and time spent driving has been the one from Daytona Beach to Florida City: 400 miles in about 12h including 3h stuck in traffic while entering Miami.

How much does it cost to drive from Chicago to Key West?

Excluding gas and food driving from Chicago to Key West costed me about $3,000 in 2022

  • $1,585 to rent the car in Chicago and return it in Miami – including full insurance
  • $312.27 to rent the convertible in Miami – including full insurance
  • $1,123 in lodging
  • $56 for the flight back to Chicago with Spirit Airlines

Day 9: Florida City FL to Key West FL
A compulsory picture of the Southernmost point in continental US


What type of car is best to drive from Chicago to Key West?

I recommend a midsize car for a number of reasons:

First of all the weather. Driving from Chicago to Key West you pass some mountainous areas where you can get some nasty storms even in summer. To this point I do not recommend taking this trip – at least not with my itinerary – anywhere close to winter: both in Illinois and on the North Carolina mountain you are likely to find snow and ice on the road.

Second: it is a long drive and you want to be as comfortable as possible to avoid back and neck-pain.

Last but not least: the cost. Unless you want to drive all the way back to Chicago (or to Key West depending where you pick up the car) you’ll need a one-way-rental. And that’s expensive. The better the car, the highest the price, goes without saying.

That said, once you reach the coast everything changes and if you can switch car to drive a convertible, well, you should do it. Just keep in mind the costs (see above: likely you are gonna drive a one-way-rental) and the season. You don’t wanna end up in Florida with a convertible during hurricanes season. Hell: yo don’t want to end up in Florida during hurricanes season with any car! Anyhow, my choice was to rent a midsize (a Volvo) in Chicago and drive it all the way to Miami where I’ve return it to pick up a Mustang convertible that got me all the way to Key West and back to Miami.

Pro tip: renting the car at the airport – and returning it at the airport – is normally much cheaper (plus you have much more options) than renting it downtown.

Can you drive from Chicago to Key West with an electric car?

I didn’t but yes, you can. You just need a little bit of additional planning to find an EV charger, but along the route you’ll find tons of opportunities to do so. Tesla Superchargers and fast-charging networks such as Electrify America and ChargePoint are available.



Chicago IL to Frankfort KY road-trip
First Stop, Frankfort: fried chicken in Kentucky is a must have, right?

Postcards from my Chicago to Key West road trip

Day 1: Chicago IL to Frankfort KY

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?


Biscuit Head, Asheville breakfast
Breakfast in Asheville: put some South in your mouth!

Day 2 and 3: Frankfort KY to Asheville NC

I started the day pretty early, hitting the Old Frankfort Pike toward Lexington: horse farms till you can see, wooden fences, lush trees, smooth turns, rolling hills and zero traffic.

Then it was drizzle and showers till North Carolina with some more heavy rain in the Tennessee branch. I took a diversion to ride the NC section of the Blue Ridge Parkway from Little Switzerland to Asheville. A gorgeous relaxing solitary 50 miles ride in and out the Blue Ridge section of the Appalachian Mountains. Felt like being in a movie, a theater play, till a tick fog came down. Curtains. Applause. End of the fun.

Asheville: a city build around dozens of breweries. A little weird place with a beautiful art district populated by art galleries, record shops, graffiti and, as I said, breweries.

  • Think of Dalston before the hipsters.
  • Bushwick without the attitude.
  • Portland minus the rain.
  • Mezzago 2005 circa with all its bloomers.

If I was living in Asheville I would spend most of my time there.


Charleston SC. My guest house, The Ashley, 201 Ashley Ave, Charleston
The room in my guesthouse in Charleston was tiny, but the building, The Ashley, incredible.

Day 4 and 5: Asheville NC to Charleston SC

Leaving Asheville during the morning rush hour meant a slow start with heavy traffic and giant trucks providing an unwelcome company. Once on the Old US Highway 25 it was another beautiful solo ride within a green lushly forest where the only worry was to avoid the suicidal furry animals crossing the road without giving any notice.

Reaching the outskirts of Charleston 8 hours later resulted in hitting the same-day-opposite-direction rush hour, a busy although spectacular entrance in the pastel colored city via the scenic Ashley River Road: an 11 miles tunnel of trees bending towards the street, as if they wanted to touch the column of vehicles passing by.

The day off driving was well spent between getting lost among colonial buildings and historical cemeteries, getting sunburned in long walks on sandy beaches, and sharing beers, fried seafood and blood with a billion mosquitoes overlooking a movie worth laguna sunset. Cause I might be an asshole but the romantic type.


Mrs. Wilkes Dining Room, 107 W Jones St, Savannah, GA 31401
One of the greatest dining experience on my life at Mrs. Wilkes Dining Room, in Savannah

Day 6: Charleston SC to Savannah GA

The shortest leg of this trip. ~200 easy, uneventful sunny miles featuring another collection of memorable tree lined roads, a few early season peach stands, some gorgeous views over the coastal wetlands and a couple of detours: one to Tybee Island, the other to tick one more item off the bucket list of dream US roads I wanna drive: Oak Avenue, a 1.5 mile long path lined by huge oak trees leading through the colonial estate of Wormsloe.

Once in Savannah it was long walks trough cobblestone-paved streets, majestic (again) trees and colorful houses, trying hard to digest the pantagruelian banquet I’ve had minutes before at Mrs Wilkes Dining Room. A legendary premises with a bunch of large communal tables crowded with food shared with strangers: fried chicken and pulled pork, cornbread and mash potatoes, black-eyed peas, okra and tomatoes, mac n cheese, gravy, multiple veggies, sausages, red rice, biscuits…

I might skip dinner.


Road-trip from Savannah to Daytona Beach
Incredible ocean views driving from Savannah to Daytona Beach

Day 7: Savannah GA to Daytona Beach FL

A few miles after leaving South Carolina it couldn’t be clearer I was in a different State: trees got shorter, palm trees more frequent, roads larger, drivers more aggressive, people louder.

A pretty forgettable drive till Jacksonville lasted longer than expected thanks to an avoidable misunderstanding between me and the mighty GPS. Once on the Scenic A1A everything got better: 114 straight miles along the Atlantic coast with an alternation of beautiful ocean views and stunning beach houses till Daytona Beach.

If Savannah was charming and elegant, Daytona Beach was quite the opposite: replace the beautiful houses with an uninterrupted line of motels, the gorgeous trees with lights and loud bars, the cobblestone paved streets with a single busy highway. The ocean and the beaches try to make up for the lack of personality but really, it’s a losing game.

Or maybe it’s just me being too old, grumpy and harsh.


Secluded beach between Daytona Beach and Miami
Driving on the scenic A1 between Daytona Beach and Fort Lauderdale you’ll meet amazing secluded beaches

Day 8: Daytona Beach FL to Florida City FL

Avoiding the highways meant the 300 miles in and out the scenic A1A from Daytona to Fort Lauderdale lasted over 8h. But they were pleasant, relaxing and enjoyable, boosting some incredible views over a multi-shades-of-blue ocean.

The remaining 40 miles from Fort Lauderdale to Miami were an awful, disheartening, deplorable shit-show. 3h stuck in traffic swearing pointlessly at everyone and everything just waiting for the next traffic light to turn red exactly in front of my crying face. On the flip side it has been a great rage relief moment. Peace now.

Note: I’ve returned the uber-reliable Volvo I’ve driven since Chicago and picked up a new car in Miami cause a grand finale deserves a grand vehicle…


The bridges connecting the Keys
Going to the Keys was one of the most memorable driving experience in my life

Day 9: Florida City FL to Key West FL

Florida City to the southernmost point in the continental United States was a straight 127 miles long line completing the 2073 miles driven since leaving Chicago 9 days ago and, given the sunny weather, switching to a convertible wasn’t a bad idea for this finale.

The Keys: long bridges connecting the islands, green and blue warm waters, briny smell coming from the ocean, palm trees everywhere, sandy beaches, roosters and chickens walking freely among locals and tourists.

Idyllic? Maybe. But I know I am a big-city person

Reminder: salads and greens for the next 2 weeks please.


Day 9: Florida City FL to Key West FL
Me on the Keys, with the Mustang I picked up in Miami. What. A. Drive!


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