The Great End-of-Summer Road Trip from Chicago to Destin

As summer draws to a close, there’s no better way to bid it farewell than by embarking on a road trip from the bustling city of Chicago to the sun-drenched beaches of Destin, Florida. This journey will take you through a diverse range of landscapes, historic towns, and exciting attractions. Whether you're a solo traveler, a couple, or a family, this road trip promises adventure and relaxation in equal measure.

Route Information

The drive from Chicago to Destin covers approximately 900 miles and takes about 14 to 15 hours, depending on traffic and how often you stop along the way. Here’s a suggested route that balances efficiency with enjoyable pit stops:

1. Start on I-57 S: Leave Chicago by taking I-57 S, which will guide you through the heart of Illinois, passing fields and farmland that offer a serene start to your journey.

2. Merge onto I-24 E near Paducah, KY: This interstate will take you through Kentucky and into Tennessee, giving you a glimpse of the changing landscapes as you move south.

3. Continue on I-65 S from Nashville, TN: Enjoy the vibrant city of Nashville, known for its rich musical history. From here, head south on I-65 S into Alabama.

4. Transition to I-65 S and US-231 S: As you enter Alabama, continue on I-65 S, then take US-231 S to weave through quaint towns and beautiful countryside.

5. Switch to US-331 S in Montgomery, AL: This final stretch will take you directly to the sandy shores of Destin, Florida.

Fun Stops Along the Way

This road trip offers plenty of opportunities to explore interesting locations. Here are some recommended stops to make the most of your journey:

1. Champaign-Urbana, IL

Home to the University of Illinois, this vibrant college town offers great food, beautiful parks, and cultural attractions. Stop by the Krannert Art Museum for a dose of art and culture.

2. Shawnee National Forest, IL

Located in southern Illinois, Shawnee National Forest offers scenic trails, rock formations, and the Garden of the Gods, a stunning natural wonder that’s perfect for a hike and some fresh air.

3. Paducah, KY

Known as the UNESCO City of Crafts and Folk Art, Paducah boasts a charming downtown area filled with galleries, shops, and eateries. Don’t miss the National Quilt Museum for something unique.

4. Nashville, TN

Take a break in Music City and enjoy live performances, historic sites like the Ryman Auditorium, and delicious Southern cuisine. Consider visiting the Country Music Hall of Fame for an immersive experience.

5. Birmingham, AL

Discover the rich history of the South by visiting the Birmingham Civil Rights Institute. Birmingham also offers a thriving food scene, making it a great place for a meal break.

6. Montgomery, AL

This city is steeped in history, with attractions such as the Rosa Parks Museum and the Alabama State Capitol. It’s an educational and inspiring stop on your journey.

Car Trip Playlist

To keep the energy up and the mood light, here’s a playlist that mixes classic road trip anthems with modern hits:

Classic Hits

1. "Route 66" by Bobby Troup
2. "Born to Run" by Bruce Springsteen
3. "American Pie" by Don McLean
4. "Sweet Home Alabama" by Lynyrd Skynyrd
5. "Ramblin' Man" by The Allman Brothers Band

Modern Tunes

1. "Shut Up and Dance" by Walk the Moon
2. "Wake Me Up" by Avicii
3. "Uptown Funk" by Mark Ronson ft. Bruno Mars
4. "Blinding Lights" by The Weeknd
5. "Rolling in the Deep" by Adele

Chill Vibes

1. "Island in the Sun" by Weezer
2. "Budapest" by George Ezra
3. "Let Her Go" by Passenger
4. "Better Together" by Jack Johnson
5. "Riptide" by Vance Joy

Upbeat and Fun

1. "Happy" by Pharrell Williams
2. "Shut Up and Dance" by Walk the Moon
3. "Can't Stop the Feeling!" by Justin Timberlake
4. "I Gotta Feeling" by The Black Eyed Peas
5. "Walking on Sunshine" by Katrina and the Waves

Final Destination: Destin

After a long journey, arriving in Destin is like stepping into paradise. Known for its sugar-white sands and emerald-green waters, Destin is a haven for beach lovers and outdoor enthusiasts.

Must-Visit Spots in Destin:

• Crab Island: This underwater sandbar is perfect for snorkeling and water sports.
• Destin Commons: A vibrant shopping and dining area with something for everyone.
• Gulfarium Marine Adventure Park: Ideal for families, offering marine shows and animal encounters.

The road trip from Chicago to Destin is a perfect way to end the summer with an epic adventure. With diverse stops, stunning scenery, and a well-curated playlist, your journey will be filled with memories as rich as the destination itself. So gather your travel companions, pack your bags, and hit the road for an unforgettable end-of-summer road trip!