Fun Road Trip Stops from Chicago to Florida

Here are restaurants, attractions and more to help break up the trip.

Have you always wanted to do the Chicago to Florida drive? The road trip can be a long drive, but there are plenty of fun things to do along the way to help break up the trip. And let’s be honest, the kids need potty breaks! 

Plus, the journey is part of the destination. We’ve rounded up our favorite family-friendly stops including Tennessee’s Chattanooga, Tallahassee and St. Louis. Here are ideas of what to do and where to stop on your Chicago to Florida road trip. 

Read more: Incredible Midwest Destinations to Visit with Kids

This article was recently updated on April 19, 2024 by Chicago Parent’s Audience Development Manager, Katina Beniaris. The update included researching and fact checking the latest information for destinations mentioned. Questions? Please reach out to

Pit stops from Chicago to Chattanooga, Tenn.

Chicago to Florida Road Trip
Photo credit: Zaharakos











World Largest’s Items in Casey

Make a road trip stop in Casey, Illinois, home to eight of the World’s Largest items including a wind chime, rocking chair, a mailbox and more! Find out what other big things you can see on the ultimate road trip stop at Casey, Illinois. 


An hour south of Indianapolis lies Columbus, Indiana, a small Midwest town known for their modern architecture. The old-time ice cream parlor and former candy shop, Zaharakos, is worth a stop for their homemade ice cream. There’s even a small museum onsite where you’ll find soda fountains and mechanical music of the past.

James A. Henderson Playground

Afterward, head across the street and let the kids run off the sugar at the playground at The Commons with the awesome, two-story Luckey Climber.

El Mazatlan

Stop at Glasgow, Kentucky but not before grabbing dinner at local favorite, El Mazatlan. The Mexican food was pretty good, but we were impressed with the large (and strong) 16 oz. margaritas for $4 (because adults need a break too)!

Mammoth Cave National Park

Have more time? Explore Mammoth Cave National Park, the largest cave system in the world.

Holiday Inn Express Hotel and Suites Glasgow

If you’re looking for a place to stay, plan a comfortable night’s stay at the Holiday Inn Express Hotel and Suites Glasgow. Gotta love the free hot breakfast in the morning!

Things to do with kids in Chattanooga, Tenn.

Chattanooga, Tenn.
Photo credit: Cheryl Eugenio
Ruby Falls at Lookout Mountain

You won’t believe how family-friendly Chattanooga was! This walkable city has so many things to do and places to eat. Do yourself a favor and plan to spend a few days in Scenic City. If you don’t have time to do all the attractions, plan to come back again.

What to do:

  • Learn about the river and ocean animals at the Tennessee Aquarium. To enhance your visit, try to schedule a backstage tour where you can feed the fish and possibly a turtle, as well as sneaking a peek of the penguins.
  • Learn about the city of Chattanooga on land and sea aboard a Chattanooga Duck, an amphibious vehicle.
  • Find your favorite flavor of moon pie (caramel or strawberry!) at the Moon Pie General Store. It’s made fresh daily at their only manufacturing plant in Chattanooga.

Where to stay: 

Pit stops from Chattanooga, Tenn. to Central Florida

Depot Park
Photo credit: Cheryl Eugenio

Lane South Orchards

We couldn’t pass by Georgia without trying some sweet Georgia peaches. Enter Lane Southern Orchards. Try their homemade peach cobbler topped with their homemade peach ice cream. Yummy!

Ellis Brothers Pecans

Georgia is also known for pecans, so we had to make a pit stop for pecans. Located right off the highway, Ellis Brothers Pecans has pecans in every flavor. Imagine aisles and aisles of pecans with samples of each. It was awesome! Hint: This is a great potty time spot — the restrooms were clean.

Depot Park

If the weather is on your side, make sure to bring bathing suits to Depot Park’s splash pad in Gainesville. Not only do they have a pretty awesome train-themed playground, but there is also trails, a general store and a museum not too far away.

Pearl’s Country Store and Barbecue

Located in a convenience store (yes, you heard that right!), Pearl’s Country Store and Barbecue, may have had the most unexpected location but it’s the best barbecue you might ever have. No joke!

Mill Creek Farm

If you happen to visit on a Saturday, stop by the Retirement Home for Horses at Mill Creek Farm. As the name suggests, 140 horses call Mill Creek Farm home. The admission is two carrots – a fantastic deal!

Holiday Inn Express and Suites Alachua – Gainesville Area

The new Holiday Inn Express and Suites Alachua – Gainesville Area was the perfect stop for us after a few hours on the road: clean, comfortable rooms, a pretty good fitness and of course, free breakfast.

Central Florida’s Polk County

Legoland Florida Resort
Photo credit: Cheryl Eugenio

Nestled between Tampa and Orlando, the biggest attraction in Central Florida Polk’s County is none other than Legoland Florida Resort.

What to do:

  • Bok Tower Gardens, a national historic landmark, has beautiful gardens to peruse including the 205-foot Singing Tower. Listen for the daily carillon concerts. The kids, however, loved exploring the 2.7-acre Hammock Hollow Children’s Garden. The kids could climb a giant spider web, build, balance across logs, create art masterpieces and cool off in the fountain It was the perfect place to connect with nature!
  • Everything is indeed awesome at Time to head back home, but not before making a road trip stop to Casey, Illinois, home to eight of the World’s Largest items including a wind chime, rocking chair, a mailbox and more! Find out what other big things you can see on the ultimate road trip stop at Casey, Illinois. What a great way to end our road trip vacation in a big way!. The kids could not get enough of the fun at Legoland Florida. We saw a Miniland on steroids, rode as many rides as we could, devoured apple fries, splashed away at Legoland Water Park and bought a few new Lego sets to add to our collection. What a fun day!

Where to stay:

  • At Hampton Inn Winter Haven, you’re no more than a five-minute drive from Legoland Florida Resort (LLFR). Who can resist the smell of popcorn in the lobby? (FREE to boot!) Parents will appreciate the complimentary hot breakfast to start the day.

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