Tips to Plan A Weekend Road Trip from Chicago to Nashville

Picture this: your whole gan packed into the car, snacks and games at the ready, and a nostalgic playlist setting the soundtrack for your adventure. You guessed it right, we’re talking about planning a weekend road trip to Nashville. If getting away from the hustle and bustle of Chicago this weekend sounds appealing, we have a jackpot in store for you!
From exploring the heart of country music to indulging in delicious Southern treats, this road trip offers something for everyone, young and old. Consider it your ticket to a whirlwind of music, culture, and memories waiting to be made.
Nashville was recently ranked among the top 3 budget-friendly family vacation spots in the country, second only to Ocean City and Niagra Falls. With its legendary musical legacy, stunning parks, and public museums covering history and art, the city is ideal for a fun family weekend in Tennessee. And the best part? Free live music around downtown!
Buckle up as we share with you three crucial tips that’ll come in handy while planning the perfect weekend road trip from Chicago to Nashville.
Tip #1: Setting the Itinerary For the Road Trip
Going on a road trip is exciting, but planning your itinerary beforehand is crucial for a smooth and enjoyable journey. Here’s how to set the perfect itinerary for your weekend road trip from Chicago to Nashville:
Before hitting the road, it’s essential to decide how many days you’ll be away. Since you’re planning a weekend trip, you’ll likely have limited time. Consider your schedule, work commitments, and the activities you want to do in Nashville. Once you’ve decided on the length of your trip, you can plan your activities accordingly.
The task of choosing the right route for the road trip comes next. From Chicago, Interstate 65 South is the most direct route to Nashville. It’s approximately a 7-8 hour drive, depending on traffic and stops.
On the other hand, for a more scenic drive, consider taking a slightly longer route with more picturesque views. Our best pick is taking the Interstate 57 South to Interstate 24 East, passing through the Shawnee National Forest in Illinois. Ending with the rolling hills of southern Kentucky, this route offers stunning landscapes for your road trip.
While you’re passing through Kentucky, how does making a pit stop for a selfie with giant dinosaurs sound? If you like the idea of it, you must visit Cave City on your way! Home to the Dinosaur World, it is a must-see roadside attraction with a colossal T.Rex welcoming you to it.
Inside, you’ll also be greeted by life-size Woolly mammoth babies and Stegosauruses, with interactive hands-on activities for the kids as a bonus. Your final pit stop before Nashville couldn’t get better than this!
Tip #2: Booking Travel Arrangements and Accommodations
Once you’ve got your itinerary all set, the next big thing to tackle is finding the perfect spot to crash in Nashville. Lucky for us, Music City’s got a little something for everyone, no matter what you’re into or how much you’re willing to spend.
If you’re all about convenience and having everything at your fingertips, downtown hotels are the way to go. They’re smack dab in the middle of all the action with easy access to Nashville’s hottest spots.
When traveling with your family, you might want to check out vacation rentals at Airbnb and VRBO. You can find the perfect pad to fit your crew from cozy apartments to spacious houses. And the best part? These come with all the comforts of home, like kitchens, multiple bedrooms, and living areas, giving you plenty of space to spread out and relax.
Oh, and don’t forget about how you’ll be getting there! If you’re not bringing your own wheels, make sure you’ve got transportation sorted. Eminent Limo notes that Sprinter vans make for an ideal road trip ride when you’re traveling with about 5-7 people.
Considering that your road trip can stretch for 14 to 16 hours, you’ll need plenty of room for the kids to take naps and unwind.
Plus, you can never really have too much space for luggage while traveling in a large group, can you? Because a Sprinter van checks all these boxes, we’d recommend you go for it to ensure a comfy road trip. Look for reliable and reputed Sprinter van rentals in Chicago to finalize your ride.
Tip #3: Researching Attractions to Visit in Advance
Now, we’ve reached the highlight of your road trip. To make the most of your weekend getaway, it’s a good idea to do a little homework and plan your visits in advance. Here’s the scoop on some must-see spots in Nashville:
The Country Music Hall of Fame
First up, we’ve got the Country Music Hall of Fame. You can’t come to Nashville, the “Music City,” and not pay homage to this iconic place. It’s like the beating heart of country music history, filled with all sorts of cool stuff like instruments, costumes, and interactive displays.
You’ll get a real feel of the journey of country music’s biggest stars, from way back when to the present day. Oh, and keep an eye on the museum’s website for any special events or exhibitions happening during your visit.
Broadway Stroll
Next, we’re hitting up Broadway. This legendary street is like the ultimate hub of live music, honky-tonks, and neon signs that’ll make your head spin—in a good way, of course!
Spend some time meandering down Broadway, ducking into bars and venues to catch live performances by some seriously talented musicians. And don’t forget to snap a selfie with the famous “I Believe in Nashville” mural for that perfect souvenir shot.
Centennial Park
Last but not least, we’ve got Centennial Park. This place is a little slice of green paradise right in the heart of downtown Nashville. Picture this: lush green lawns, walking paths winding through beautiful gardens, and the cherry on top—the full-scale replica of the Parthenon from Athens, Greece.
What’s even more exciting is that the park is set to undergo new renovations under a project funded with $10 million!
Starting earlier this year, these renovations include a brand new pavilion spread across 6,000 square feet alongside Lake Watauga. With an expected collective capacity of 1,650 people, the pavilion will become the first structure built here since 1963. Witnessing its construction will be like seeing history in the making first-hand. Isn’t that exciting?
Frequently Asked Questions (FAQs)
What’s the best time of the year to visit Nashville?
While Nashville is a popular attraction all year long, it’s most beautiful during the fall months. Between September to November, the cooler temperatures of the city are ideal for exploring its beautiful parks and going on long, scenic drives. You’ll also get to attend the Tennessee State Fair around this time.
What should I pack for a weekend road trip?
Packing for a weekend road trip needs a balance of essentials and a few extras. Go with comfortable clothing and shoes appropriate for outdoor activities. Don’t forget to take a first aid kit alongside your basic toiletries. Lastly, pack your driver’s license, vehicle documents, chargers, power banks, and snacks and drinks for the road.
Is Nashville safe for tourists?
Yes, Nashville is generally considered safe for tourists. However, you must practice cautionary measures like planning ahead, drinking responsibly, and keeping emergency contacts on standby. Moreover, while traveling in your own vehicle, make it a point to follow traffic rules and keep your valuables secure.
Alrighty, now you’re all set for an epic weekend road trip from Chicago to Nashville! With these tips under your belt, you can go ahead, hit the road, and make some unforgettable memories with your crew.



