Trippy
 
  Questions  
Drive      Fly      Stay      Login    Signup

Chicago to Key West via Naples (Florida)

driving   /   4 days   /   no pets   /   no RV

Chicago to Key West road trip planner

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.

customize this trip
 Day 1

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

4:51 pm  Louisville
stay overnight at 21C Museum Hotel
leave the next day around 9:00 am

day 1 driving ≈ 5 hours
find more stops

 Day 2

9:00 am  leave from 21C Museum Hotel
drive for about 2.5 hours

11:38 am  Nashville
eat at Bluebird Cafe
stay for about 4 hours
and leave at 3:38 pm
drive for about 3.5 hours

7:20 pm  Atlanta
stay overnight at W Atlanta - Midtown
leave the next day around 10:00 am

day 2 driving ≈ 6.5 hours
find more stops

 Day 3

10:00 am  leave from W Atlanta - Midtown
drive for about 3.5 hours

1:16 pm  Valdosta
stay for about 1 hour
and leave at 2:16 pm
drive for about 4 hours

6:06 pm  Tarpon Springs
stay overnight and leave the next day around 10:00 am

day 3 driving ≈ 7 hours
find more stops

 Day 4

10:00 am  leave from Tarpon Springs
drive for about 3 hours

12:53 pm  Naples (Florida)
stay for about 1 hour
and leave at 1:53 pm
drive for about 5 hours

6:45 pm  arrive in Key West
eat at Blue Heaven Restaurant
stay at Casa Marina, A Waldorf Astoria Resort

day 4 driving ≈ 7.5 hours
find more stops

drive this trip in  


From:
To:
Depart:
Return:
Get:    
  Change your route
From:
To:
 
  Alternate route
Enter a city to drive through, or find all trips from Chicago to Key West.
Via:
 

Chicago to Key West questions

profile  Scott asked:
How to get there  (1 answer)

profile  Kelly asked:
want to travel by mississipi river  (1 answer)

profile  Ellen asked:
RV stops  (0 answers)


Where should I stop along the way?

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?
        Safe area?

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
        Basa Restaurant
        Milkwood 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:
        Bluebird Cafe
        Opryland Hotel
        Pancake Pantry
        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

Atlanta  (143 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:
        The Varsity
        Mary Mac's Tea Room
        Antico Pizza Napoletana
        Empire State South
        JCT Kitchen & Bar
    hotels around Atlanta:
        W Atlanta - Midtown
        The Westin Peachtree Plaza
        Artmore Hotel
        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?

Valdosta  (5 answers)

Tarpon Springs  (4 answers)
    Honeymoon Island State Park  (3 mentions)

Naples (Florida)  (20 answers)
    questions about Naples (Florida):
        Seafood restaurants
        Good restaurants? Fun things to do?
        Bachelorette party activities in Naples, Florida?
        Restaurant Recommendations in Naples?


Where's the best place to stay in Key West?

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.




Where's the best place to eat in Key West?

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:

Louie's Backyard  (3 mentions)
Half Shell Raw Bar  (3 mentions)
Garbo's Grill  (2 mentions)
Hot Tin Roof  (2 mentions)

Want to research more popular restaurants in Key West? Click the blue button below.




What are some things to do in Key West?

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:

Duval Street  (3 mentions)
Mallory square  (3 mentions)
Sloppy Joe's Bar  (2 mentions)

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!

For example, here are some questions people have asked about Key West. Click on any question to see answers from the community!

profile  Cathy from Michigan asked:
Good hotel and things to do with 8 year old son.  (4 answers)

profile  ross from Chicago asked:
Great non touristy restaurants in key west  (3 answers)

profile  Bernadette from Ohio asked:
Driving from Miami to key west- where to stop and eat?  (2 answers)

profile  Karisa from Atlanta asked:
Things to do and places to eat/drink in Key West?  (2 answers)

profile  Tim from River Ridge, Louisiana asked:
Key West on a budget  (2 answers)

Click the button below to explore more questions and answers related to Key West.




Do I really have to go back home?

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!

Want to plan the trip back? Get the reverse directions for a Key West to Chicago drive, or go to the main page to plan a new road trip.

You can also compare the travel time if you're flying or driving by calculating the distance from Chicago to Key West. Or get a full Chicago to Key West flight plan.

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!





At a Glance
without making any stops
total driving distance is 1,602 miles
driving time of 24 hours, 11 minutes
328 Chicago travel answers
41 Indianapolis travel answers
47 Louisville travel answers
190 Nashville travel answers
143 Atlanta travel answers
5 Valdosta travel answers
4 Tarpon Springs travel answers
20 Naples (Florida) travel answers
64 Key West travel answers





VIEW DETAILED MAP





   
Questions   ·   Destinations   ·   Drive   ·   Fly   ·   Airports   ·   Stay   ·   Search

Login   ·   About   ·   FAQ   ·   Feedback   ·   Privacy   ·   Terms