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Road trip from Chicago to Ocala
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Museums
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Nightlife
Food & Drink
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ITINERARY
20h 0m1,076 miles14 stops
1
Depot Park
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
2
The Chopping Block
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
3
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
4
Boystown
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
5
Wrigley Field
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
6
The Grill
7
Tennessee State Museum
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
8
Bicentennial Capitol Mall State Park
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
9
Jackalope Brewing Company - The Ranch
Jackalope Brewing Company's taproom and brewery The Ranch offers locally hand-crafted beers, brewery tours, small bites, and a dog-friendly outdoor patio.
10
Lane Motor Museum
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
11
River Gallery
Craft and art collections.
12
Johnny's Hideaway
13
Ponce City Market
14
Underground Atlanta
Known as “the city beneath the city,” Underground Atlanta has been the cultural heart of Downtown Atlanta since the 1900s. From basement speakeasies to the annual Peach Drop (where an 800-pound peach is dropped from the top of a building to ring in the new year), this arts, entertainment, and retail district has seen it all. Today, Underground Atlanta offers a multifaceted cultural experience featuring a virtual reality gallery, music clubs, and restaurants. travelers can also enjoy outdoor concerts, festivals, artisan markets, and more. This vibrant hub is conveniently connected to the Five Points train station, and just a short stroll from the scenic Broad Street Boardwalk. – Tripadvisor
Customize this Trip
OVERVIEW
Embark on an epic adventure from the bustling streets of Chicago to the heart of Florida's horse country, Ocala. This incredible journey weaves through diverse landscapes, from towering skyscrapers to rolling hills and lush forests. Along the way, uncover hidden gems, immerse yourself in vibrant cultures, and create memories that will last a lifetime.
As you leave Chicago behind, the urban sprawl gives way to tranquil farmlands and charming small towns. Marvel at the vibrant fall foliage or the vibrant wildflowers that paint the fields in spring. Visit historic landmarks that tell tales of America's past, and indulge in local flavors at cozy roadside diners. The journey takes you through the vibrant Smoky Mountains, where majestic peaks and cascading waterfalls await exploration.
As you approach Ocala, the rolling hills and verdant pastures signal your arrival in horse country. Immerse yourself in the equestrian culture, visit world-class horse farms, and witness the grace of these magnificent animals. Explore the natural beauty of Silver Springs State Park, where crystal-clear waters and lush vegetation create a serene oasis. The journey culminates in the vibrant city of Ocala, where Southern charm meets modern amenities, offering a perfect blend of relaxation and excitement.
1
Start:Depot Park
Gainesville, Florida·
5.0
(94) review
Depot Park is a signature city park in downtown Gainesville providing a space for unique public outdoor enjoyment. Depot features a children's adventure play area with a custom splash pad of waterfalls, water soakers, and ground jets. A water's edge promenade hosts special events like food truck rallies, art festivals, and musical performances. The park is fully staffed and free of charge.
2
Start:The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
3
Start:Michigan Avenue Bridge
Chicago, Illinois·
4.5
(985) review
The view from the bridge is one of the best vistas the city has to offer.
4
Start:Boystown
Chicago, Illinois·
4.5
(98) review
Located in Chicago's North Side, this vibrant neighborhood is known for its exciting nightlife and for being one of the largest LGBTQIA+ communities in the city. It's the host of the annual Chicago Pride Parade, and a must-see in the area is the Legacy Walk on Halsted Street, where you can learn about the contributions of the LGBTQIA+ community while admiring the colorful street art and rainbow crosswalks. Check out the unique shops and then grab a bite at one of the area's delicious Thai or Mexican restaurants. At night, visit one of the neighborhood's bars to enjoy a drag show, concert, and tasty cocktail. Consider taking a food or walking tour of Chicago that stops by Boystown. – Tripadvisor
5
Start:Wrigley Field
Chicago, Illinois·
4.5
(9953) review
Get a behind-the-scenes look at the legendary home of the Chicago Cubs with Wrigley Field Tours. Built in 1914, this must-see Chicago attraction houses more than 100 years of history. New this year, fans can join us on a non-gameday Ivy Tour which includes the opportunity to take a photo in front of Wrigley Field’s historic ivy wall.
6
Start:The Grill
Indianapolis, Indiana·
3.5
(9) review
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
7
Start:Tennessee State Museum
Nashville, Davidson County, Tennessee·
4.5
(997) review
The Tennessee State Museum is located at the corner of Rosa L. Parks Blvd. and Jefferson Street at Bicentennial Capitol Mall State Park. It is designed to bring history to life. It includes a “Tennessee Time Tunnel” chronicling the state’s rich history and leading visitors though the Museum’s permanent collection, a hands-on children’s gallery, six rotating galleries, a state-of-the art digital learning center and a two-story Grand Hall. Exhibitions include significant artifacts related to the state’s history, along with displays of art, furniture, textiles, and photographs produced by Tennesseans. The Museum's Civil War holdings of uniforms, battle flags and weapons are among the finest in the nation.There is no admission charge for visitors. Hours are subject to change. Please check our website at tnmuseum.org for the most up to date information on parking, exhibitions and events.
8
Start:Bicentennial Capitol Mall State Park
Nashville, Davidson County, Tennessee·
4.5
(969) review
This 19 acre park in the heart of Nashville serves as a monument to the bicentennial celebration of the State of Tennessee. This park offers plenty of opportunities to learn about the long history of Tennessee while having a great experience in a beautiful green space. More information on this park and many more can be found at the TN State Parks website.
9
Start:Jackalope Brewing Company - The Ranch
Nashville, Davidson County, Tennessee·
4.5
(9) review
Jackalope Brewing Company's taproom and brewery The Ranch offers locally hand-crafted beers, brewery tours, small bites, and a dog-friendly outdoor patio.
10
Start:Lane Motor Museum
Nashville, Davidson County, Tennessee·
4.5
(971) review
Lane Motor Museum in Nashville features the largest European collection of cars and motorcycles in the United States. Admission for adults aged 18-64 is $15; Admission for Youths aged 6-17 is $3; Admission for seniors 65+ is $10; Children under 5 are always free. There is plenty of FREE parking.
11
Start:River Gallery
Chattanooga, Tennessee·
4.5
(98) review
Craft and art collections.
12
Start:Johnny's Hideaway
Atlanta, Georgia·
3.5
(95) review
3771 Roswell Rd NE, Atlanta, GA 30342-4414
13
Start:Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
14
Start:Underground Atlanta
Atlanta, Georgia·
2.0
(976) review
Known as “the city beneath the city,” Underground Atlanta has been the cultural heart of Downtown Atlanta since the 1900s. From basement speakeasies to the annual Peach Drop (where an 800-pound peach is dropped from the top of a building to ring in the new year), this arts, entertainment, and retail district has seen it all. Today, Underground Atlanta offers a multifaceted cultural experience featuring a virtual reality gallery, music clubs, and restaurants. travelers can also enjoy outdoor concerts, festivals, artisan markets, and more. This vibrant hub is conveniently connected to the Five Points train station, and just a short stroll from the scenic Broad Street Boardwalk. – Tripadvisor
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
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Frequently Asked Questions
What's the driving distance between Chicago and Ocala?
The distance is 1,076 miles
What's the travel time between Chicago and Ocala?
The driving time can vary depending on traffic conditions, but it is typically 20h 0m mins in normal traffic
What are some of the best cities to visit between Chicago and Ocala?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Ocala?
There are plenty! Here are some stops you shouldn’t miss on your way to Ocala
What’s the weather like in Ocala?
The weather in Ocala is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Ocala in January
Weather in Ocala in February
Weather in Ocala in March
Weather in Ocala in April
Weather in Ocala in May
Weather in Ocala in June
Weather in Ocala in July
Weather in Ocala in August
Weather in Ocala in September
Weather in Ocala in October
Weather in Ocala in November
Weather in Ocala in December
Interested in a detailed plan for your time in Ocala?
Plan your dream Ocala trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Ocala
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Where else can I travel to if I'm starting my trip in Chicago?
We have a lot of great trip options for Chicago! See the links below for all the itineraries we created for you
