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By Huuk Team

Road trip from Chicago to Kissimmee

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ITINERARY

21h 33m1,162 miles13 stops
1
Depot Park
200 SE Depot Ave, Gainesville, FL 32601-7004
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
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.
3
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
4
WestShore Plaza
250 WestShore Plaza, Tampa, FL 33609-1918
5
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.
6
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
7
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.
8
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.
9
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.
10
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.
11
River Gallery
400 E 2nd St, Chattanooga, TN 37403-1105
Craft and art collections.
12
Ponce City Market
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
13
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
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OVERVIEW

Get ready for an epic adventure from the vibrant streets of Chicago to the magical world of Kissimmee! Along the way, you'll embark on a journey filled with endless possibilities and unforgettable experiences. Embrace the adventure as you venture through bustling cities, picturesque landscapes, and enchanting destinations. Each mile will be a chapter in your travel story, filled with unique encounters and memories to cherish forever. Prepare yourself for an extraordinary odyssey that will leave an everlasting mark on your soul.

As you cruise through the heartland of America, immerse yourself in the rich tapestry of diverse cultures, iconic landmarks, and hidden gems. Discover the hidden treasures nestled within charming towns and vibrant metropolises. Marvel at the architectural wonders that grace the skylines of major cities, each telling a tale of innovation and human ingenuity. Indulge in the flavors of local cuisines, tantalizing your taste buds with a symphony of culinary delights. From bustling markets to cozy cafes, every meal will be an adventure in itself.

Immerse yourself in the wonders of nature as you traverse through majestic mountains, serene lakes, and sprawling plains. Feel the wind in your hair and the sun on your skin as you embark on breathtaking hikes, bike rides, and kayaking excursions. Witness the grandeur of cascading waterfalls, explore hidden coves, and marvel at the kaleidoscope of colors that paint the sky at sunset. Embrace the tranquility of nature's embrace, creating memories that will last a lifetime.

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.
200 SE Depot Ave, Gainesville, FL 32601-7004
2
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
3
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
4
WestShore Plaza
Tampa, Florida·
4.0
(99) review
250 WestShore Plaza, Tampa, FL 33609-1918
5
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
6
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
7
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
8
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
9
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
10
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
11
River Gallery
Chattanooga, Tennessee·
4.5
(98) review
Craft and art collections.
400 E 2nd St, Chattanooga, TN 37403-1105
12
Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
13
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

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Kissimmee?
The distance is 1,162 miles
What's the travel time between Chicago and Kissimmee?
The driving time can vary depending on traffic conditions, but it is typically 21h 33m mins in normal traffic
What are some of the best cities to visit between Chicago and Kissimmee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Kissimmee?
There are plenty! Here are some stops you shouldn’t miss on your way to Kissimmee
What’s the weather like in Kissimmee?
The weather in Kissimmee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Kissimmee in January
Weather in Kissimmee in February
Weather in Kissimmee in March
Weather in Kissimmee in April
Weather in Kissimmee in May
Weather in Kissimmee in June
Weather in Kissimmee in July
Weather in Kissimmee in August
Weather in Kissimmee in September
Weather in Kissimmee in October
Weather in Kissimmee in November
Weather in Kissimmee in December
Interested in a detailed plan for your time in Kissimmee?
Plan your dream Kissimmee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Kissimmee
A 2-day itinerary in Kissimmee
A 3-day itinerary in Kissimmee
A 4-day itinerary in Kissimmee
A 5-day itinerary in Kissimmee
A 6-day itinerary in Kissimmee
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
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