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By Huuk Team

Road trip from Chicago to Orlando

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ITINERARY

21h 31m1,156 miles18 stops
1
Michigan Avenue Bridge
333 Michigan Ave, Chicago, IL 60601-3901
The view from the bridge is one of the best vistas the city has to offer.
2
Boystown
Chicago, IL
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
3
Wrigley Field
1060 W. Addison St., Chicago, IL 60613-4566
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.
4
Tennessee State Museum
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
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.
5
Bicentennial Capitol Mall State Park
600 James Robertson Pkwy, Nashville, TN 37243-3081
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.
6
Lane Motor Museum
702 Murfreesboro Pike, Nashville, TN 37210-4522
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.
7
River Gallery
400 E 2nd St, Chattanooga, TN 37403-1105
Craft and art collections.
8
The Spice & Tea Exchange of Chattanooga
2115 Gunbarrel Rd Suite A-13, Chattanooga, TN 37421-2674
Come In and Smell the Spices! The Spice & Tea Exchange® offers food lovers, chefs, and tea enthusiasts a unique shopping experience filled with culinary delights. Explore your inner chef and shop over 140 fine spices, 75+ hand-mixed seasoning blends, sugars, salts, loose-leaf teas, and accessories. Create your own gourmet gift, or choose from a variety of gift boxes and recipe samplers!
9
Johnny's Hideaway
3771 Roswell Rd NE, Atlanta, GA 30342-4414
10
Ponce City Market
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
11
State Farm Arena
1 State Farm Drive, Atlanta, GA 30303-2723
Philips Arena, named for founding partner Philips Electronics and home of the NHL’s Atlanta Thrashers, NBA’s Atlanta Hawks and WNBA's Atlanta Dream, has hosted many top tours and events including: U2, Rolling Stones, Paul McCartney, Bruce Springsteen, Kenny Chesney, Ringling Bros. and Barnum & Bailey, Disney On Ice, Harlem Globetrotters, Sesame Street Live and so many more!
12
Underground Atlanta
50 Upper Alabama St SW, Atlanta, GA 30303-3192
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
13
Young's Paso Fino Ranch
7950 NW 80th Ave, Ocala, FL 34482-1112
14
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
15
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
16
1001 Transportation
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
17
American Girl Orlando
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
18
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
Customize this Trip

OVERVIEW

Get ready for an unforgettable adventure as we embark on an epic road trip from the bustling metropolis of Chicago to the enchanting sunshine state of Florida. Along the way, we'll discover hidden gems, marvel at breathtaking landscapes, and create memories that will last a lifetime. Our journey begins in the heart of the Windy City, where towering skyscrapers and vibrant streets set the stage for our adventure. As we leave the urban jungle behind, we'll traverse rolling hills and lush forests, passing quaint towns and charming villages nestled amidst picturesque countryside.

As we drive further south, the landscape transforms into a symphony of colors and textures. We'll encounter vast farmlands, witness the gentle sway of cornfields, and admire the vibrant hues of blooming wildflowers. The air fills with the sweet scent of blooming trees, and the gentle breeze whispers tales of the journey ahead. Along the way, we'll make pit stops at roadside attractions, savor local delicacies at cozy diners, and immerse ourselves in the rich history and culture of the regions we pass through.

As we approach our final destination, the sun-drenched beaches of Orlando beckon us with their promise of endless summer fun and unforgettable experiences. We'll explore thrilling theme parks, meet beloved characters, and create memories that will warm our hearts for years to come. This road trip is not merely a journey from one place to another; it's an adventure that will ignite your imagination, create lasting bonds, and leave you with a treasure trove of cherished memories.

1
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.
333 Michigan Ave, Chicago, IL 60601-3901
2
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
Chicago, IL
3
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.
1060 W. Addison St., Chicago, IL 60613-4566
4
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.
1000 Rosa L Parks Blvd, Nashville, TN 37208-2624
5
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.
600 James Robertson Pkwy, Nashville, TN 37243-3081
6
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.
702 Murfreesboro Pike, Nashville, TN 37210-4522
7
River Gallery
Chattanooga, Tennessee·
4.5
(98) review
Craft and art collections.
400 E 2nd St, Chattanooga, TN 37403-1105
8
The Spice & Tea Exchange of Chattanooga
Chattanooga, Tennessee·
5.0
(92) review
Come In and Smell the Spices! The Spice & Tea Exchange® offers food lovers, chefs, and tea enthusiasts a unique shopping experience filled with culinary delights. Explore your inner chef and shop over 140 fine spices, 75+ hand-mixed seasoning blends, sugars, salts, loose-leaf teas, and accessories. Create your own gourmet gift, or choose from a variety of gift boxes and recipe samplers!
2115 Gunbarrel Rd Suite A-13, Chattanooga, TN 37421-2674
9
Johnny's Hideaway
Atlanta, Georgia·
3.5
(95) review
3771 Roswell Rd NE, Atlanta, GA 30342-4414
10
Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
11
State Farm Arena
Atlanta, Georgia·
4.5
(912) review
Philips Arena, named for founding partner Philips Electronics and home of the NHL’s Atlanta Thrashers, NBA’s Atlanta Hawks and WNBA's Atlanta Dream, has hosted many top tours and events including: U2, Rolling Stones, Paul McCartney, Bruce Springsteen, Kenny Chesney, Ringling Bros. and Barnum & Bailey, Disney On Ice, Harlem Globetrotters, Sesame Street Live and so many more!
1 State Farm Drive, Atlanta, GA 30303-2723
12
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
50 Upper Alabama St SW, Atlanta, GA 30303-3192
13
Young's Paso Fino Ranch
Ocala, Florida·
4.0
(9) review
7950 NW 80th Ave, Ocala, FL 34482-1112
14
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
15
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
16
1001 Transportation
Orlando, Florida·
5.0
(98) review
Airport Transportation Affordable flat rate Orlando & Miami ground transportation with over 20 years of combined experience. Our chauffeurs have earned an excellent reputation for exceptional standard of safety, reliability and professionalism Transportation in Orlando & Miami Florida.
6401 Time Square Ave Cu-20 #1022, Orlando, FL 32819-9118
17
American Girl Orlando
Orlando, Florida·
4.5
(98) review
Discover a place like no other, where lifelong memories are made, time together counts, and girls can be girls! Enjoy casual dining in the Bistro, where dolls are always welcome.
8001 S Orange Blossom Trl, Orlando, FL 32809-7654
18
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Orlando?
The distance is 1,156 miles
What's the travel time between Chicago and Orlando?
The driving time can vary depending on traffic conditions, but it is typically 21h 31m mins in normal traffic
What are some of the best cities to visit between Chicago and Orlando?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Orlando?
There are plenty! Here are some stops you shouldn’t miss on your way to Orlando
What’s the weather like in Orlando?
The weather in Orlando is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Orlando in January
Weather in Orlando in February
Weather in Orlando in March
Weather in Orlando in April
Weather in Orlando in May
Weather in Orlando in June
Weather in Orlando in July
Weather in Orlando in August
Weather in Orlando in September
Weather in Orlando in October
Weather in Orlando in November
Weather in Orlando in December
Interested in a detailed plan for your time in Orlando?
Plan your dream Orlando trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Orlando
A 2-day itinerary in Orlando
A 3-day itinerary in Orlando
A 4-day itinerary in Orlando
A 5-day itinerary in Orlando
A 6-day itinerary in Orlando
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