Here's a sample itinerary for a drive from Chicago to Jacksonville. If you're planning a road trip to Jacksonville, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Chicago and Jacksonville. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Chicago, Illinois.
You can enter an exact street address if you want to get precise directions, but this is optional.
Since there are only 2 travelers, we assume you're driving 1 car. You can adjust the number of people traveling at the top. We assume a maximum of 4 passengers per car, but you can change the number of cars to fit your situation.
Indianapolis Museum of Art (4 mentions)
Louisville (37 answers)
Louisville Slugger Museum & Factory (3 mentions)
Churchill Downs (2 mentions)
Muhammad Ali Center (2 mentions)
Fourth Street Live! (2 mentions)
Louisville Slugger Field (2 mentions)
restaurants around Louisville:
Seviche, A Latin Restaurant
Jeff Ruby's Louisville
Hyatt Regency Louisville
hotels around Louisville:
21C Museum Hotel
The Galt House Hotel And Suites
The Brown Hotel
questions about Louisville:
What is your favorite restaurant in Louisville?
Any cool things to do/places to eat in Louisville?
Want to spend our money on Bourbon, not hotels
What's the best neighborhood in Louisville for a first time visitor?
Hotels to stay at during the Kentucky Derby?
Nashville (147 answers)
Grand Ole Opry (8 mentions)
Country Music Hall of Fame (6 mentions)
Ryman Auditorium (6 mentions)
Centennial Park (6 mentions)
The Parthenon (5 mentions)
restaurants around Nashville:
Hattie B's Hot Chicken - 19th Ave
Peg Leg Porker BBQ
questions about Nashville:
Nearby small towns or outdoor areas?
Top of the line hotels in Nashville?
What are some must sees in Nashville during the weekend
Best Location to Stay
Hotel by Airport
Chattanooga (25 answers)
Ruby Falls (5 mentions)
Rock City (3 mentions)
Tennessee Aquarium (2 mentions)
Creative Discovery Museum (2 mentions)
Lookout Mountain (2 mentions)
questions about Chattanooga:
Activities in Chattanooga for families with active kids
Is April 2015 a good month to visit Chattanooga?
Atlanta (111 answers)
Georgia Aquarium (29 mentions)
World of Coca-Cola (20 mentions)
Piedmont Park (16 mentions)
Midtown Atlanta (14 mentions)
High Museum of Art (11 mentions)
restaurants around Atlanta:
Mary Mac's Tea Room
Antico Pizza Napoletana
Empire State South
JCT Kitchen & Bar
hotels around Atlanta:
W Atlanta - Midtown
The Westin Peachtree Plaza
Glenn Hotel, Autograph Collection
The Highland Inn
questions about Atlanta:
Good Restaurants Unique to Atlanta?
Great, reasonable places to eat.
Tourist spots worth seeing in Atlanta?
Authentic Southern Food!
Best family activities in Atlanta?
Macon (4 answers)
Valdosta (4 answers)
Your final destination is Jacksonville, Florida.
You can enter the exact street address of your destination, but this is optional.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
Of course, Trippy is the perfect place to ask questions because there's an entire community of travelers talking to each other and sharing tips and advice. Trippy is where you can get answers personalized for your tastes, budgets, trip dates & more!
Click the button below to explore more questions and answers related to Jacksonville.
Yes, even this step is optional, because if you're on vacation who wants the trip to end? It's okay, you can start planning your next trip!
Don't forget about exploring your own hometown with a staycation. You can also find some cool day trips or get away for a weekend. Maybe try typing in a faraway location like London, Hong Kong, or Sydney, and get inspired for your dream trip around the world.
And if you know Chicago well, please help your fellow travelers and answer their questions about Chicago!