Here's a sample itinerary for a drive from Fort Myers to Chicago. If you're planning a road trip to Chicago, you can research locations to stop along the way. Traveling with a dog or cat? View pet-friendly stops between Fort Myers and Chicago. Camping along the way? View RV campgrounds between Fort Myers and Chicago. Find the best hotels, restaurants, and attractions based on the most talked about places recommended by Trippy members.
Your starting point is Fort Myers, Florida.
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.
Tampa (56 answers)
International Plaza and Bay Street (6 mentions)
Busch Gardens Tampa (5 mentions)
Bayshore Blvd (4 mentions)
Tampa Riverwalk (4 mentions)
South Howard Ave (3 mentions)
restaurants around Tampa:
Piquant Hyde Park
Bern's Steak House
questions about Tampa:
Best new restaurants in Tampa?
Popular areas in Tampa for shopping?
Beaches around Tampa
Best free things to do in Tampa?
Weekend ideas for a first timer in Tampa
Valdosta (4 answers)
Macon (3 answers)
Atlanta (109 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
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?
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?
Nashville (149 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
hotels around Nashville:
Gaylord Opryland Resort
The Hermitage Hotel
Omni Nashville Hotel
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
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
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?
Indianapolis (28 answers)
Indianapolis Museum of Art (4 mentions)
Indianapolis Zoo (2 mentions)
questions about Indianapolis:
What is your favorite restaurant in Indianapolis?
Awesome food trucks?
Best free things to do in Indianapolis?
Your Favorite Holiday Events in Indianapolis
Your final destination is Chicago, Illinois.
You can enter the exact street address of your destination, but this is optional.
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 Chicago.
You can also see most people recommend as the best amount of time to visit. Find out how many days in Chicago to stay.
If you're looking for a quick answer, you can check out The James Chicago Hotel, which was mentioned 12 times on Trippy.
Here are some more hotels people talk about:
Want to research more popular hotels in Chicago? Click the blue button below.
Need some recommendations on somewhere to get food?
Trippy members suggest Lou Malnati's Pizzeria, which was mentioned 36 times.
Here are some more restaurants people talk about:
Want to research more popular restaurants in Chicago? 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 Chicago.
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 Fort Myers well, please help your fellow travelers and answer their questions about Fort Myers!