The Open Road Travel

The Best Chicago To Florida Road Trip Stops

With a road trip from Chicago to Florida (Orlando) taking over 17 hours, our advice is to split the journey over multiple days to make it enjoyable. There are plenty of great places to stay on the drive from Chicago to Orlando, but the following three destinations are the best Chicago to Florida road trip stops.

Indianapolis, Indiana

Indiana’s capital and largest city, Indianapolis, is renowned for its sports heritage, featuring the Indianapolis Motor Speedway & Museum, Lucas Oil Stadium, and Gainbridge Fieldhouse. The downtown area is pedestrian-friendly with attractions such as Monument Circle, the Indiana State Museum, and the Children's Museum of Indianapolis. Nature enthusiasts can explore the Central Canal Walk and White River State Park, home to the Indianapolis Zoo. The city also boasts a growing culinary scene with farm-to-table dining, craft breweries, and a farmers' market.

Other key attractions include the Eiteljorg Museum of American Indians and Western Art and the Newfields art museum complex.

Best Hotel To Stay At In Indianapolis – JW Marriott Indianapolis

JW Marriott Indianapolis is a 4-star hotel in the city centre, recognised as Indiana's tallest hotel with 1,013 guest rooms featuring panoramic views.



Each room includes comfortable furniture and linens, modern amenities such as a 40-inch LCD flat-screen cable TV, Wi-Fi, iPod docking stations, air conditioning, and coffee makers. The hotel offers various dining options, a 24-hour fitness centre, and over 100,000 square feet of event space, including a large ballroom. Breakfast and parking are available upon request.

Nashville, Tennessee

Tennessee’s capital and most populous city, Nashville, is known as "Music City USA" for its significant role in country music production. Music enthusiasts can enjoy tours of historic venues and various bars featuring live music. For non-music lovers, attractions like the Tennessee State Capitol, numerous museums, and professional sports teams offer diverse entertainment options.

Key attractions include the Grand Ole Opry, Country Music Hall of Fame and Museum, Ryman Auditorium, Honky Tonk Highway, Johnny Cash Museum, National Museum of African American Music, Belle Meade Historic Site & Winery, and The Parthenon.



Best Hotel To Stay At In Nashville, Tennessee – Sheraton Music City Nashville

The Sheraton Music City is a spacious, 4-star hotel featuring Georgian architecture. It offers comfortable rooms with amenities such as a flat-screen TV, a refrigerator, a coffee machine, and a private balcony or patio. The hotel is pet-friendly and features Wi-Fi, indoor and outdoor pools, a sun deck, a fitness centre, a bar, a restaurant, a gift shop, vending machines, and a free airport shuttle service.

Atlanta, Georgia

Atlanta, the capital and largest city of Georgia, holds significant historical importance as a central location during the American Civil War in the 1860s and as a key organising hub for the civil rights movement in the 1960s, led by figures like Martin Luther King Jr. The city is essential for understanding the culture and history of the southern United States.

Key attractions include the Georgia Aquarium, World of Coca-Cola, Martin Luther King, Jr. National Historical Park, Atlanta Botanical Garden, High Museum of Art, Centennial Olympic Park, Piedmont Park, and Stone Mountain Park.

Best Hotel To Stay At In Atlanta, Georgia – Reverb by Hard Rock Atlanta Downtown

REVERB Downtown Atlanta is a music-inspired hotel located in the heart of downtown Atlanta, ideal for visitors seeking modern comfort and proximity to entertainment. Situated near major venues such as Mercedes-Benz Stadium and State Farm Arena, it features 195 advanced rooms with smart technology, including voice-activated lighting and music, inviting beds, and thoughtful décor.



The hotel includes unique "Roadie" rooms for larger groups, complimentary Wi-Fi, a fitness centre, and communal spaces. Dining options include the Constant Grind café and bar and the rooftop RT60 Lounge, which offers skyline views and live music. Its location provides easy access to attractions like Centennial Olympic Park and the Georgia Aquarium.

The Best Attractions On A Road Trip From Chicago To Florida (Orlando)

Gary, Indiana

Gary, Indiana, located on the south shore of Lake Michigan, is known for its industrial history and cultural significance, having been founded in 1906 by U.S. Steel. Key attractions include Michael Jackson's childhood home, the Gary SouthShore RailCats stadium, and the Indiana Welcome Center that showcases regional heritage. Nearby, Indiana Dunes National Park offers beautiful beaches, dunes, hiking trails, and water activities.

Louisville, Kentucky

Louisville, Kentucky's largest city, is famous for its Southern charm and history, particularly the Kentucky Derby, held every May. The city has a strong culinary scene featuring bourbon-infused dishes and the Hot Brown sandwich, plus many local distilleries on the Kentucky Bourbon Trail.

Key attractions include the Muhammad Ali Center and the Louisville Slugger Museum & Factory.  Outdoor activities include the scenic waterfront, parks by Frederick Law Olmsted, and the Big Four Bridge connecting to Indiana.

Bardstown, Kentucky

Bardstown, Kentucky, known as the "Bourbon Capital of the World," features 11 distilleries within 16 miles of Court Square, including Heaven Hill Bourbon Experience and Lux Row Distillers. Visitors can enjoy guided tours, tastings, and the chance to bottle their own bourbon.

The annual Kentucky Bourbon Festival adds to the town’s charm, while its history is reflected in nearly 200 historic buildings, including the Federal Hill mansion and the Civil War Museum. Dining options include The Rickhouse, Scout & Scholar Brewery, and gourmet experiences on "My Old Kentucky Dinner Train."

Jim Beam Distillery

The Jim Beam Distillery, a key site on the Kentucky Bourbon Trail, offers visitors insight into bourbon-making rooted in over two centuries of tradition. The "Beam Made Bourbon" tour covers the entire production process, from grain selection to ageing, with tastings included. Additionally, the Fred B. Noe Distillery showcases the creation of small-batch and experimental bourbons, while the "Tasting & Storytelling Experience" highlights the Beam family's history.



The Kitchen Table restaurant complements the experience with bourbon-infused Southern cuisine, set against the backdrop of Bernheim Forest.

Fort Knox

Fort Knox is a significant U.S. Army installation known for the U.S. Bullion Depository. While vault tours require a permit, visitors can view the exterior and learn its history at the visitor centre.

Nearby attractions include the General George Patton Museum of Leadership, which features exhibits on General Patton, military vehicles, and personal artefacts; the Kentucky Museum of American Pocketknives, home to the world's largest pocketknife; and Tioga Falls waterfall.

Mammoth Cave National Park

Mammoth Cave National Park, established on July 1, 1941, is the 26th oldest national park in the U.S. and a UNESCO World Heritage Site. It features the world's longest known cave system, with over 400 miles of explored passageways, surpassing the combined lengths of South Dakota’s Jewel Cave and Wind Cave. The park offers guided cave tours which cater to various interests and fitness levels, along with a Visitor Center for information and amenities.



Above ground, visitors can explore 52,000 acres of hills, forests, and rivers, and engage in activities such as hiking, canoeing, and camping, with accommodations available at Mammoth Cave Hotel.

Bowling Green, Kentucky

Bowling Green, Kentucky’s 3rd largest city, boasts attractions such as the National Corvette Museum, GM Corvette Assembly Plant, NCM Motorsports Park, and Historic RailPark & Train Museum. Outdoor activities include hiking at Lost River Cave, which also hosts an underground boat tour. Chaney's Dairy Barn offers local ice cream. Beech Bend Park combines a drag strip, amusement park, and water park. Downtown’s Fountain Square Park is home to local shops, restaurants, and cultural venues like SKyPAC.

Historic Mansker’s Station

Historic Mansker’s Station in Goodlettsville, Tennessee, is an 18th-century attraction within 200-acre Moss-Wright Park, featuring a reconstructed 1779 log fort and the 1787 Bowen Plantation House, the oldest brick residence in Middle Tennessee. Established by frontiersman Kasper Mansker as a refuge for settlers, the fort showcases historical defensive strategies and daily life of the era. The Bowen Plantation House, built by Captain William Bowen, illustrates domestic life on the frontier. Guided tours of both structures are available Monday to Friday, led by guides in period attire.



Lynchburg, Tennessee

Lynchburg, Tennessee, is a small town known for the Jack Daniel’s Distillery, where visitors can tour the historic facility and enjoy tastings. The downtown square showcases local shops and restaurants offering Southern cuisine. Lynchburg hosts seasonal festivals and live music, emphasising its community spirit and Southern charm, making it a memorable destination.

Chattanooga, Tennessee

Chattanooga, Tennessee’s 3^rd-largest and 4^th-most populous city, played a crucial role during the American Civil War due to its significant railroad connections, famously associated with the song "Chattanooga Choo Choo." The city is also influential in various transportation sectors. It features numerous attractions and museums related to this theme, along with diverse entertainment options in art, literature, and nature.

Nantahala National Forest

Nantahala National Forest spans over 500,000 acres, offering lush mountain scenery and activities such as hiking, biking, camping, and whitewater rafting on the Nantahala River. It features a diverse range of tree species, including oaks, pines, tulip poplars, and maples, contributing to beautiful Fall foliage and picturesque waterfalls, viewable from spots like Wayah Bald.

Jackson, Georgia

Jackson, Georgia, known as the "Gate City of Butts County," is a charming town noted for its rich history and Southern hospitality. Recently, Jackson has gained popularity among fans of the show Stranger Things, as it features numerous filming locations and associated attractions.



Key attractions include the Jackson Historic District with shops and restaurants, the Butts County Historical Society Museum, Indian Springs State Park, the historic Indian Springs Hotel, Dauset Trails Nature Center, and High Falls State Park.

Macon, Georgia

Macon, Georgia’s 4th most populous and 3rd largest city by area, was founded in 1809 and is known for its rich musical heritage. It produced artists like Little Richard, Otis Redding, and Jason Aldean. The city features historic districts with antebellum architecture, parks, and Southern cuisine, particularly celebrated during the cherry blossom season.

Key attractions include Ocmulgee Mounds National Historical Park, The Allman Brothers Band Museum, Hay House, the Museum of Arts and Sciences, and Rose Hill Cemetery.

Osceola National Forest & Wildlife Management Area

Osceola National Forest and Osceola Wildlife Management Area, established in December 1974, spans 190,932 acres in north-central Florida. Named after Seminole warrior Osceola, it preserves diverse wildlife and habitats, hosting endangered species and other animals, including alligators, black bears, and bobcats. The area is popular for outdoor activities like camping, hiking, and fishing, making it an ideal stop to break up a drive.



Jacksonville, Florida

Jacksonville, the largest city by area in the contiguous United States and Florida's most populous city, is known for its tropical climate and nine major bridges. The city offers numerous attractions, including museums, golf courses, beaches, and parks, making it less touristy than other major Florida cities. This accessibility makes Jacksonville a great stop for experiencing “The Sunshine State’s” culture and history on a road trip from Chicago to Florida.

St. Augustine, Florida

St. Augustine, established by Spanish colonists in 1565, is the oldest continuously inhabited city in the U.S. It served as Florida's capital from 1821 to 1824 and offers a rich array of historical attractions, including diverse architecture spanning many eras and some of the country's oldest monuments, churches, and museums. Beyond history, the city features amphitheatres, aquariums, and state parks, making it a vibrant destination for all visitors.

Daytona Beach, Florida

The final stop on a drive from Chicago to Orlando, Florida, is Daytona Beach. Located in Florida's "Fun Coast," it is famous for its beautiful beaches and waterfront attractions. It is notably linked to motorsports, hosting events such as Daytona Bike Week, the second-largest motorcycle rally in the U.S., and Biketoberfest in October. The city is also the birthplace of NASCAR, housing its headquarters and the Daytona International Speedway, making it a key location for fans to explore the sport's history.

Final Thoughts On Planning A Road Trip From Chicago To Florida (Orlando)

That concludes our guide to planning the best road trip from Chicago to Florida (Orlando). You should now have all the information you need to make the trip as enjoyable as possible, from when to go and which route to use to where to stay and what to see along the way. All you have left to do is work out what to take with you and start budgeting and booking everything, so you can look forward to enjoying it all for yourself as soon as possible.



If you need help planning where to stay to begin your trip in Chicago, this article should help. Those interested in continuing the drive may also enjoy our guides on the ultimate Florida road trip itinerary or a road trip from Orlando, Florida, to New Orleans, Louisiana.