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Chicago to Key West via Lexington

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

10:00 am  start in Chicago
drive for about 3 hours

1:00 pm  Indianapolis
stay for about 1 hour
and leave at 2:00 pm
drive for about 3 hours

5:05 pm  Lexington
stay overnight and leave the next day around 11:00 am

day 1 driving ≈ 6 hours
find more stops

 Day 2

11:00 am  leave from Lexington
drive for about 5.5 hours

4:33 pm  Atlanta
stay overnight at W Atlanta - Midtown
leave the next day around 10:00 am

day 2 driving ≈ 5.5 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 3.5 hours

5:36 pm  Orlando
eat at Cafe Tu Tu Tango
stay overnight at Universal's Cabana Bay Beach Resort
leave the next day around 9:00 am

day 3 driving ≈ 6.5 hours
find more stops

 Day 4

9:00 am  leave from Universal's Cabana Bay Beach Resort
drive for about 3.5 hours

12:22 pm  Miami
eat at Versailles
stay for about 3.5 hours
and leave at 3:52 pm
drive for about 3.5 hours

7:14 pm  arrive in Key West
eat at Blue Heaven Restaurant
stay at Casa Marina, A Waldorf Astoria Resort

day 4 driving ≈ 6.5 hours
find more stops

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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?

Lexington  (28 answers)
    questions about Lexington:
        What is your favorite restaurant in Lexington?
        Best place to stay in Lexington while attending the Rolex 3 day event?
        stays overnight, Lexington, Ky. near highway

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)

Orlando  (159 answers)
    The Wizarding World Of Harry Potter  (16 mentions)
    Universal CityWalk  (8 mentions)
    Universal's Islands of Adventure  (7 mentions)
    Universal Studios Islands of Adventure  (5 mentions)
    Orlando Premium Outlets - International Dr  (5 mentions)
    restaurants around Orlando:
        Cafe Tu Tu Tango
        Emeril's Orlando
        SeaWorld
        Jimmy Buffett's Margaritaville
        Hard Rock Cafe
    hotels around Orlando:
        Universal's Cabana Bay Beach Resort
        Grand Bohemian Hotel Orlando, Autograph Collection
    questions about Orlando:
        How many days for Disney + universal?
        5 days in orlando not Disney
        What to do during one day in Orlando that's not Disney World
        Top golf courses in Orlando?
        Fine dining for client meeting in Orlando

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:
        Versailles
        Joe's Stone Crab
        Puerto Sagua Restaurant
        Seasons 52
        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


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 1,575 miles
driving time of 25 hours, 24 minutes
328 Chicago travel answers
41 Indianapolis travel answers
28 Lexington travel answers
143 Atlanta travel answers
5 Valdosta travel answers
159 Orlando travel answers
143 Miami travel answers
64 Key West travel answers





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