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Chicago to Key West via New Orleans

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 3.5 hours

1:35 pm  Altamont
stay for about 1 hour
and leave at 2:35 pm
drive for about 4.5 hours

7:11 pm  Memphis
stay overnight at Peabody Hotel
leave the next day around 10:00 am

day 1 driving ≈ 8 hours
find more stops

 Day 2

10:00 am  leave from Peabody Hotel
drive for about 6 hours

4:06 pm  New Orleans
stay overnight at Hotel Monteleone
leave the next day around 9:00 am

day 2 driving ≈ 6 hours
find more stops

 Day 3

9:00 am  leave from Hotel Monteleone
drive for about 5.5 hours

2:27 pm  Tallahassee
stay for about 1 hour
and leave at 3:27 pm
drive for about 3.5 hours

7:08 pm  Orlando
stay overnight at Universal's Cabana Bay Beach Resort
leave the next day around 10:00 am

day 3 driving ≈ 9 hours
find more stops

 Day 4

10:00 am  leave from Universal's Cabana Bay Beach Resort
drive for about 4 hours

1:53 pm  Coral Gables
stay for about 1 hour
and leave at 2:53 pm
drive for about 2.5 hours

5:29 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?

Altamont

Memphis  (114 answers)
    Beale Street  (9 mentions)
    Graceland  (9 mentions)
    National Civil Rights Museum  (8 mentions)
    Memphis Zoo  (7 mentions)
    Mud Island  (6 mentions)
    restaurants around Memphis:
        Central BBQ
        Gus's World Famous Fried Chicken
        Charlie Vergos Rendezvous
        Payne's Bar-B-Q
        Cozy Corner Restaurant
    hotels around Memphis:
        Peabody Hotel
    questions about Memphis:
        What's the best neighborhood in Memphis for a first time visitor?
        What are the musts of Memphis, y'all?
        Must sees in Memphis TN?? Hidden gems places to eat??
        Best blues clubs in Memphis?
        Good Food and Fun With Kids

New Orleans  (230 answers)
    Frenchmen Street  (47 mentions)
    Bourbon Street  (26 mentions)
    Jackson Square  (18 mentions)
    The Spotted Cat Music Club  (13 mentions)
    Magazine Street  (13 mentions)
    restaurants around New Orleans:
        Café du Monde
        French Quarter
        Commander's Palace Restaurant
        K-Paul's Louisiana Kitchen
        Muriel's Jackson Square
    hotels around New Orleans:
        Hotel Monteleone
        The Ritz-Carlton, New Orleans
        The Westin New Orleans Canal Place
        Royal Sonesta Hotel New Orleans
        The Roosevelt New Orleans
    questions about New Orleans:
        Breakfast in New Orleans?
        What is your favorite restaurant in New Orleans?
        Where can I find the best jazz bars in New Orleans?
        What are the must-try foods and restaurants in NOLA?
        When is the best time to go to New Orleans?

Tallahassee  (13 answers)
    questions about Tallahassee:
        Best free things to do in Tallahassee?
        Pet friendly hotel

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

Coral Gables  (16 answers)
    Vizcaya Museum and Gardens  (9 mentions)
    Bayside Marketplace  (9 mentions)
    Pérez Art Museum Miami  (8 mentions)
    Wynwood Walls  (7 mentions)
    Wynwood Arts District  (5 mentions)
    restaurants around Coral Gables:
        Versailles
        Seasons 52
        Dolphin Mall
        Eating House Miami
        Wynwood Kitchen & Bar
    questions about Coral Gables:
        Any good restaurants in Coral Gable?
        What is your favorite restaurant in Coral Gables?


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 1,946 miles
driving time of 28 hours, 31 minutes
328 Chicago travel answers
1 Altamont travel answer
114 Memphis travel answers
230 New Orleans travel answers
13 Tallahassee travel answers
159 Orlando travel answers
16 Coral Gables travel answers
64 Key West travel answers





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