From the shores of Lake Michigan to the bright lights of Miami Beach, this Chicago to Florida road trip will take you through the heart of the Midwest and deep into the South. All you need is an empty stomach and a full tank of gas.
Whether you are looking to migrate south from the cold winters of Chicago or want to immerse yourself in America from top to bottom, nothing beats a drive through the Midwest and into the South. As you follow our ultimate Chicago to Florida road trip, you will cruise the Crossroads of America, sing along with the country stars of Nashville and eat your way through Southern cooking before you relax at the end of your journey on the beaches of Miami.
Stops
1. Chicago
2. Indianapolis, IN
3. Louisville, KY
4. Nashville, TN
5. Atlanta, GA
6. Miami, FL
Info at a glance
- A 14-day trip
- Type of route: City
- 6 stops along the route
- 1,385 miles of driving
Highlights
- Visit the Mecca of the Midwest in Chicago, Illinois.
- Cross through the Heartland of America in Indianapolis, Indiana.
- Horse around at Churchill Downs in Louisville, Kentucky.
- See the next great music star in Nashville, Tennessee.
- Party with the stars in Miami, Florida.
Getting to the start
Begin your journey from the western shores of Lake Michigan as you kick off the road trip in Chicago, Illinois. A popular way to arrive in Chicago is via train, and Union Station of Chicago is one of the most prominent stations in America as well as the flagship station of Amtrak for the Midwest. If you are flying into Chicago, you have two major airports to choose from—O’Hare International Airport or Midway Airport. For drivers, Chicago lies in the center of Interstate 90, I-94, I-290, and I-55.
When to Visit
The best time to make this road trip is during the fall months, between late October and November. You can enjoy the beautiful foliage of the Midwest, avoid major snowstorms as you travel through the colder regions, and still enjoy a moderate climate when you drive through the South and arrive in Florida. Pack outfits with layers since you may have to adjust as you drive from state to state and experience different climates. Don’t forget your swimsuit as the tropical waters of Miami Beach will be calling your name once you arrive.
Driving tips
This road trip route involves tolls for bridges and turnpikes, with some states offering a contactless payment in which the bill is sent to your mailing address after your journey and other states requiring a cash or card payment to continue on the route. This will vary from state to state, and sometimes from bridge to bridge. Be sure to pay attention to signs as you approach payment stations so you can know what to expect. The speed limits will range from 55 miles per hour in urban zones to 75 mph outside of cities.
What to know about the route
After leaving the bright lights of Chicago, take I-90 and I-65 southbound until you reach the Crossroads of America—Indianapolis, Indiana. From there, you will continue along I-65 all the way to Louisville, Kentucky. The road trip route stays simple, with the next leg of your journey involving I-65 South to Nashville, Tennessee. You will then take I-24 and I-75 until you arrive in Atlanta, Georgia. When you are ready for the final leg of your drive, get back onto I-75 and travel through Orlando onto the Florida Turnpike, which will bring you to the heart of downtown Miami. If you are driving this route in the fall or winter months, we recommend an all-wheel-drive SUV to handle any unexpected snow flurries. For drives in the summer and spring, a smaller sedan will help you save money on gas and navigate the streets of larger cities.
Chicago
As the river flows under bridges and through downtown while cars zoom by on Lower Wacker Drive, the bustling serenity of Chicago is impossible to deny. This city has earned its nickname as the Mecca of the Midwest with its towering skyscrapers, including the iconic Willis Tower and John Hancock Center, and unique landmarks, such as Cloudgate (The Bean) and the Chicago Riverwalk.
Points of interest
There may not be a more famous ballpark in existence than Wrigley Field, home of the Chicago Cubs. With the iconic outfield wall covered in ivy, this stadium has been the setting for memorable moments in both sports and cinema (we see you, Ferris Bueller). For a fun-filled evening, head to Navy Pier and watch the sun dip below the skyline from the top of the Ferris wheel.
Where to eat, drink and sleep
Deep. Dish. Pizza. That’s it; that’s our advice. Head over to the original purveyor, Giordano’s, and order a pie to experience this iconic dish for yourself. If you still have room, find a Chicago Red Hot joint and enjoy this spicy favorite. For dessert, make your way to the Beverly neighborhood and try out the Original Rainbow Cone (since 1926)—a cake cone stacked with chocolate, strawberry, vanilla with cherries and walnuts, pistachio and sherbet.
Sixt Insider Tip
If you are driving along Lower Wacker Drive and it seems familiar, it’s not just you. This was the filming location for the iconic truck chase scene in The Dark Knight between Batman and the Joker. If you look to the right as you drive north on this underground street, you might spot the Batman symbol painted on the wall in the spot where the Joker fired his bazooka, only to be thwarted again by Batman himself.
From Chicago to Indianapolis (185 miles)
About halfway between Chicago and Indianapolis is Fair Oaks, Indiana—home to The Dairy Adventure. This is a dairy-themed roadside attraction with interactive exhibits, rides and movie screenings. You can even see newborn calves in the birthing barn and watch as they learn to walk for the first time.
Indianapolis, IN
With so many freeways leading into the city, it’s no wonder that Indianapolis is nicknamed The Crossroads of America. Because of its connection to motor vehicles, this is also known as the Racing Capital of the World. The Indianapolis 500, the largest single-day sporting event in the world, takes place each year over Memorial Day Weekend at the Indianapolis Motor Speedway.
Points of interest
Even if you are not in town for the Indy 500, you can visit the Indianapolis Motor Speedway Museum to learn about the race and find out why race winners pour milk all over themselves. For those traveling with kids, Indianapolis also has the largest children’s museum in the world—The Children’s Museum of Indianapolis. In the downtown area, you can find a series of war monuments so extensive that only Washington, D.C. has a larger collection.
Sixt Insider Tips
In the early 1800s, construction on a canal through Indianapolis was abandoned. It was left unused until 1985 when it was restored and transformed into a central aspect of the city. Make your way to Riverside Park and stroll along the canal or take a paddleboat through the heart of downtown Indianapolis.
From Indianapolis to Louisville (115 miles)
Give yourself a jolt of adrenaline with a visit to Fear Fair, a haunted house located in Seymour, Indiana. Whether you are driving through on Halloween or in the middle of the summer, this attraction is the perfect way to stretch your legs and test your nerves.
Louisville, KY
If you are wondering which stop marks the transition between the Midwest and South, look no further—Louisville is known as the Gateway to the South. This city has produced everything from famous athletes like Muhammad Ali to famous food like Kentucky Fried Chicken. Louisville has deep roots in athletics, with the reliable Louisville Slugger baseball bats being produced here since 1856 and the Kentucky Derby running at Churchill Downs since 1875.
Points of interest
Learn what makes the Louisville Slugger the preferred bat of baseball players at the Louisville Slugger Museum and Factory. While the Kentucky Derby is held on the first weekend in May, you can visit the Kentucky Derby Museum year-round. If you have ever wanted to ride an underground zipline through a 17-mile limestone mine, check out the Mega Cavern.
Where to eat, drink and sleep
As the home of Colonel Sanders, it should come as no surprise that fried chicken is an iconic dish for Louisville restaurants. However, there is much more than this timeless favorite, including the Hot Brown (an open-face turkey sandwich topped with bacon) and Burgoo (a classic southern stew made with meat and vegetables). Save room for a slice of Derby Pie for dessert, made with walnuts, pecans and melted chocolate.
Sixt Insider Tip
Louisville is brimming with history, and nowhere displays that better than the historic Frankfort Avenue. With locally owned restaurants, shops that have been family-run for generations and picturesque buildings, you will feel as though you have stepped back in time when you visit this neighborhood.
From Louisville to Nashville (175 miles)
As you make the drive to Nashville on I-65 South, switch out your car for some real horsepower with a visit to the Jesse James Riding Stables. Learn how to ride a horse from experienced guides and take a tour through Jesse James Cave, named after the famous Wild West outlaw who rode his horses into the mountains to hide after robbing stagecoaches and banks.
Nashville, TN
As you make your way deeper into the South, Nashville stands out like a beacon of arts and culture. Often referred to as the Athens of the South, this city prides itself on music, education, food and friendly people. It even has a replica of the Parthenon from Greece, with an extensive collection of art and statues inside. More than anything, this city is known for producing country music stars, with aspiring artists flocking from around the world to get their shot at fame.
Points of interest
As such a musical hotspot, Nashville is home to several melodious museums like the Musicians Hall of Fame and Museum, the Country Music Hall of Fame and the Johnny Cash Museum. For a live music experience unlike any other, make your way to Lower Broadway Street—nicknamed Honky Tonk Highway—and hop from bar to bar listening to live bands and singers.
Where to eat, drink and sleep
The only thing that might be more associated with Kentucky than fried chicken is bourbon. With distilleries throughout the region, you can’t go wrong with a tour. One that stands out is Nelson’s Green Brier Distillery. With a history dating to the 1800s when it was founded by a German immigrant, this distillery offers the chance to taste authentic Kentucky Bourbon and learn a bit along the way.
Sixt Insider Tips
If you want to get away from the bar scene, catch a show at the Grand Ole Opry or take a tour of this historic venue. After hosting country stars like Carrie Underwood, Keith Urban and Brad Paisley, this stage is waiting for the next great musician to step up; you just might be lucky enough to catch their first big show.
From Nashville to Atlanta (250 miles)
Break up your drive with a stop in Chattanooga, Tennessee, where you can visit the Bluff View Art District. This neighborhood is located on a bluff overlooking the Tennessee River and features public artwork and plenty of cafes and restaurants to recharge for your journey.
Atlanta, GA
While other cities may appear to be a concrete jungle, Atlanta is known for its dense tree coverings, even earning the nickname “City in a Forest.” With its unique blend of nature and historic architecture, this city has outdoor opportunities like Piedmont Park and entertainment options like the renowned Fox Theatre. From the American Civil War to the Civil Rights Movement, Atlanta has played a prominent role in history, which you can still see by walking the streets of its historic districts.
Points of interest
Make time for a visit to the childhood home of civil rights leader Martin Luther King, Jr. From his former church at Ebenezer Baptist Church to his final resting place, the Martin Luther King, Jr. National Historic Park offers the chance to walk in the footsteps of an icon. To explore more of the city on foot, use the Atlanta Beltline. The Beltline includes 2,000 acres of parks, 33 miles of trails and 22 miles of streetcar lines in case you get too tired.
Sixt Insider Tips
Atlanta has also earned its reputation as the “Hollywood of the South,” with plenty of television shows and movies being filmed here. Take a guided tour of the city to learn which of your favorite films were shot here, from The Walking Dead to the Avengers franchise. You might even recognize a few streets just from walking around the city, so keep your eye out.
From Atlanta to Miami (660 miles)
We know this is a long stretch of driving, so reward yourself with a stop in the Theme Park Capital of the World—Orlando. From the Wizarding World of Harry Potter to the Walt Disney World Resort, you can step into another dimension of entertainment. There is even a full-size replica of the Millenium Falcon at Star Wars: Galaxy’s Edge. Even if you only have 12 parsecs, you can make this work.
Miami, FL
Warm, tropical waters splash gently upon white sandy beaches as the towering skyscrapers of downtown Miami look over the coast. If this sounds like a place you want to be, then you share the feeling with famous stars like Will Smith and Jennifer Lopez who have come to call Miami their home. With the protected waters of Biscayne Bay, this is the perfect opportunity to break out that swimsuit and work on your tan for a few days.
Points of interest
There is no denying that Miami is known for its beaches, and you have plenty to choose from—Miami Beach, South Beach, Sunny Isles Beach and Golden Beach are some favorites. Dive into the Cuban heritage of Miami with a visit to Little Havana, where you can experience everything from competitive Dominos to Cuban coffee and cuisine.
Where to eat, drink and sleep
With such deep roots in nearby Cuba, the food scene in Miami has been inspired by immigrants who brought their cooking style to their new home. Try out a Cuban coffee, also known as Café Cubano—a sweetened espresso shot. Another classic is the Cuban Sandwich, pork and ham topped with Swiss cheese, pickles and mustard between two slices of bread.
Sixt Insider Tip
While this city may be known for its bright lights and bustling nightlife, it also has a deep commitment to nature preservation. Just south of the city is Biscayne National Park, where you can cruise across the surface of the water on an airboat and come face-to-face with manatees, sea turtles and, of course, the American Alligator. With nearly 200,000 acres to explore, this park absolutely deserves a spot on your itinerary.
