Here's a sample itinerary for a drive from Chicago to Key West. If you're planning a road trip to Key West, you can research locations to stop along the way. Make sure you check road conditions to double check the weather. Traveling with a dog or cat? Find pet-friendly stops. Camping along the way? Search for RV campgrounds. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
11:00 am start in Chicago
drive for about 3 hours
2:00 pm Indianapolis
stay for about 1 hour
and leave at 3:00 pm
drive for about 2 hours
day 1 driving ≈ 5 hours
find more stops
9:00 am leave from 21C Museum Hotel
drive for about 2.5 hours
8:00 pm Montgomery
stay overnight and leave the next day around 10:00 am
day 2 driving ≈ 7 hours
find more stops
10:00 am leave from Montgomery
drive for about 6.5 hours
4:31 pm Ocala
stay overnight and leave the next day around 9:00 am
day 3 driving ≈ 6.5 hours
find more stops
9:00 am leave from Ocala
drive for about 4.5 hours
1:18 pm Miami
stay for about 3.5 hours
and leave at 4:48 pm
drive for about 3.5 hours
day 4 driving ≈ 7.5 hours
find more stops
Indianapolis (41 answers)
Indianapolis Museum of Art (4 mentions)
Indianapolis Zoo (2 mentions)
questions about Indianapolis:
What is your favorite restaurant in Indianapolis?
Your Favorite Holiday Events in Indianapolis
Best free things to do in Indianapolis?
Awesome food trucks?
Louisville (47 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?
What's the best neighborhood in Louisville for a first time visitor?
Any cool things to do/places to eat in Louisville?
Hotels to stay at during the Kentucky Derby?
Has anyone been to Butchertown Market?
Nashville (190 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:
What's the best neighborhood in Nashville for a first time visitor?
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
Montgomery (12 answers)
Ocala (4 answers)
Miami (143 answers)
Miami Beach (22 mentions)
Lincoln Road (14 mentions)
Lincoln Road Mall (11 mentions)
Ocean Drive (9 mentions)
Vizcaya Museum and Gardens (9 mentions)
restaurants around Miami:
Joe's Stone Crab
Puerto Sagua Restaurant
The Broken Shaker
questions about Miami:
What is your favorite restaurant in Miami?
Good Cuban food in Miami?
What is the weather like during the winter months?
one night lay over in Miami- what to see, where to eat?
Unsafe neighborhoods in Miami
Are you going straight to a hotel, or looking for a vacation rental or Airbnb?
The best resource on neighborhoods, areas, and hotels is the Trippy page on where to stay in Key West.
If you're looking for a quick answer, you can check out Casa Marina, A Waldorf Astoria Resort, which was mentioned 2 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in Key West? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Blue Heaven Restaurant, which was mentioned 8 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Key West? Click the blue button below.
This section could be endless, so rather than trying to suggest every local activity or attraction, we'll leave it open-ended.
These are some of the places people talk about on Trippy:
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 Key West.
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!