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By Huuk Team

Road trip from Chicago to Lakeland

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ITINERARY

21h 44m1,159 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
Ponce City Market
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
9
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
10
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.
11
Ocala Palms Golf & Country Club
5174 NW 26th St, Ocala, FL 34482-3250
12
Marion Theatre
50 S Magnolia Ave, Ocala, FL 34471-1153
13
Island H2O Water Park
3230 Inspiration Dr, Kissimmee, FL 34747
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
14
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
15
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
16
University of South Florida Botanical Gardens, Tampa
4202 E Fowler Ave, Tampa, FL 33620-5150
17
Al Lopez Park
4810 N Himes Ave, Tampa, FL 33614-6614
Two popular flat loops, .8 and 1.2-miles, through the woods.
18
Bayshore Boulevard
312 Bayshore Blvd, Tampa, FL 33611
Home of the world's longest sidewalk.
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OVERVIEW

Get ready for an exciting adventure as we embark on a thrilling journey from the bustling city of Chicago to the serene landscapes of Lakeland. Along the way, we'll traverse diverse terrains, witness breathtaking sceneries, and create unforgettable memories. The journey will be filled with laughter, discovery, and a touch of adventure, making it an experience that will stay with us long after we reach our destination.

As we set off from the vibrant streets of Chicago, the towering skyscrapers will gradually give way to rolling hills and vast farmlands. The landscape will transform before our eyes, painting a picturesque canvas of nature's beauty. We'll make our way through charming towns and historic landmarks, each with its own unique story to tell. Along the way, we'll encounter friendly locals, eager to share their knowledge and traditions, making our journey even more enriching.

As we approach Lakeland, the scenery will shift once again, revealing tranquil lakes, lush forests, and rolling hills. The air will fill with the sweet scent of blooming flowers, and the sound of birdsong will create a symphony of nature. We'll have the opportunity to explore this scenic paradise, whether it's by hiking through verdant trails, paddling across sparkling lakes, or simply relaxing amidst the tranquil surroundings. The journey from Chicago to Lakeland promises to be an unforgettable adventure, filled with discovery, wonder, and lasting memories that will be cherished for a lifetime.

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
Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
9
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
10
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
11
Ocala Palms Golf & Country Club
Ocala, Florida·
4.5
(9) review
5174 NW 26th St, Ocala, FL 34482-3250
12
Marion Theatre
Ocala, Florida·
4.5
(90) review
50 S Magnolia Ave, Ocala, FL 34471-1153
13
Island H2O Water Park
Kissimmee, Florida·
3.5
(96) review
Island H2O Water Park is your place for family fun! Tube slides, raft riding & splash zones, plus luxury cabana rentals at a sprawling water park.
3230 Inspiration Dr, Kissimmee, FL 34747
14
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
15
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
16
University of South Florida Botanical Gardens, Tampa
Tampa, Florida·
3.5
(98) review
4202 E Fowler Ave, Tampa, FL 33620-5150
17
Al Lopez Park
Tampa, Florida·
4.0
(97) review
Two popular flat loops, .8 and 1.2-miles, through the woods.
4810 N Himes Ave, Tampa, FL 33614-6614
18
Bayshore Boulevard
Tampa, Florida·
4.5
(972) review
Home of the world's longest sidewalk.
312 Bayshore Blvd, Tampa, FL 33611

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Lakeland?
The distance is 1,159 miles
What's the travel time between Chicago and Lakeland?
The driving time can vary depending on traffic conditions, but it is typically 21h 44m mins in normal traffic
What are some of the best cities to visit between Chicago and Lakeland?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Lakeland?
There are plenty! Here are some stops you shouldn’t miss on your way to Lakeland
What’s the weather like in Lakeland?
The weather in Lakeland is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Lakeland in January
Weather in Lakeland in February
Weather in Lakeland in March
Weather in Lakeland in April
Weather in Lakeland in May
Weather in Lakeland in June
Weather in Lakeland in July
Weather in Lakeland in August
Weather in Lakeland in September
Weather in Lakeland in October
Weather in Lakeland in November
Weather in Lakeland in December
Interested in a detailed plan for your time in Lakeland?
Plan your dream Lakeland trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Lakeland
A 2-day itinerary in Lakeland
A 3-day itinerary in Lakeland
A 4-day itinerary in Lakeland
A 5-day itinerary in Lakeland
A 6-day itinerary in Lakeland
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