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By Huuk Team

Road trip from Leesburg to Chicago

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ITINERARY

20h 48m1,113 miles25 stops
1
MetroWest Golf Club
2100 S Hiawassee Rd, Orlando, FL 32835-6307
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2
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.
3
The Legends Walk Course
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
4
Teatro Martini
6400 Carrier Dr, Orlando, FL 32819-8260
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
5
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.
6
Lake Rianhard
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
7
Corpus Christi Catholic Church
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
8
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.
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
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!
11
Ponce City Market
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
12
Johnny's Hideaway
3771 Roswell Rd NE, Atlanta, GA 30342-4414
13
River Gallery
400 E 2nd St, Chattanooga, TN 37403-1105
Craft and art collections.
14
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.
15
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.
16
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.
17
Masterpiece Mixers Paint and Party Studio
8021 Dixie Hwy Suite 105, Louisville, KY 40258-1300
Get out and get creative! Unleash your inner artist at our upbeat painting parties. Join a regular class or book a private party and our super fun instructors will walk you step-by-step in creating your masterpiece. Great for birthday parties, girls night out, date night, bridal showers, company events and more.
18
Angel's Envy Distillery
500 E Main Street, Louisville, KY 40202-1002
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
19
Barrels & Billets
800 W Main St, Louisville, KY 40202-2620
An exciting bourbon experience where guests can blend, create and bottle their very own bourbon. Guests will blend with six award-winning WoodCraft bourbons which includes a 200 Year Oak, European Oak, American Oak, Cherry Wood, Maple Wood, and Smoked Oak. During the experience, guests will learn the art of bourbon blending before the blending process begins. Once the blending experience is complete, guests can have their recipe bottled onsite.
20
The Grill
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
21
Smiley
5729 E 86th St, Indianapolis, IN 46250-1560
Smiley is a huge 25,000 sq foot facility in Castleton filled with the latest Virtual Reality technology. We have very rare and unique interactive games and rides for children of all ages. Our playgrounds are for age 9 months to 10 years old and our VR spaces are for ages 9 years and up! We also have an enormous indoor playground with trampoline basketball, tubes & slides, rock-climbing, obstacle
22
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.
23
The Chopping Block
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
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.
24
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
25
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.
Customize this Trip

OVERVIEW

Leesburg to Chicago
1
Start:MetroWest Golf Club
Orlando, Florida·
3.0
(96) review
MetroWest Golf Club, voted the best golf course in Orlando, is located just minutes away from Universal Orlando Resort. The club provides a fair, yet demanding challenge to make a pleasurable golf experience for players of all skill levels.
2100 S Hiawassee Rd, Orlando, FL 32835-6307
2
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
3
The Legends Walk Course
Kissimmee, Florida·
4.0
(96) review
8505 W Irlo Bronson Memorial Hwy Orange Lake Resort, Kissimmee, FL 34747-8217
4
Teatro Martini
Orlando, Florida·
4.5
(960) review
When the sun goes down at the circus, the acts get hotter, the laughs get bigger, and everything gets a whole lot crazier. Award winning acts from around the world will amaze and astound while the best of the best perform on the stage and all around you. Laugh till you can’t breath, watch till you can’t believe, and celebrate what happens when you finally get to see Teatro Martini. Located in Orlando, Florida, in the heart of I-Drive, this highly interactive show features circus performers from around the world including comedy magician, clowns, acrobats and performing puppies!
6400 Carrier Dr, Orlando, FL 32819-8260
5
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
6
Lake Rianhard
Celebration, Orlando, Florida·
4.5
(95) review
701 Front St Em frente a Market Street, Celebration, Orlando, FL 34747-4915
7
Corpus Christi Catholic Church
Celebration, Orlando, Florida·
5.0
(99) review
1050 Celebration Ave, Celebration, Orlando, FL 34747-4867
8
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
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
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
11
Ponce City Market
Atlanta, Georgia·
4.5
(992) review
675 Ponce de Leon Ave NE, Atlanta, GA 30308-1884
12
Johnny's Hideaway
Atlanta, Georgia·
3.5
(95) review
3771 Roswell Rd NE, Atlanta, GA 30342-4414
13
River Gallery
Chattanooga, Tennessee·
4.5
(98) review
Craft and art collections.
400 E 2nd St, Chattanooga, TN 37403-1105
14
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
15
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
16
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
17
Masterpiece Mixers Paint and Party Studio
Louisville, Kentucky·
5.0
(9) review
Get out and get creative! Unleash your inner artist at our upbeat painting parties. Join a regular class or book a private party and our super fun instructors will walk you step-by-step in creating your masterpiece. Great for birthday parties, girls night out, date night, bridal showers, company events and more.
8021 Dixie Hwy Suite 105, Louisville, KY 40258-1300
18
Angel's Envy Distillery
Louisville, Kentucky·
4.5
(967) review
Built in the heart of Louisville, the ANGEL’S ENVY Distillery is downtown’s first fully operational whiskey production facility. Co-founded in 2010 by the late Master Distiller Lincoln Henderson, ANGEL’S ENVY began as a passion project that combined their family’s deep-rooted passion for and knowledge of the industry with an innovative outlook on bourbon making and finishing. ANGEL’S ENVY opened the doors in 2016 and puts you in the center of our distilling process for a unique tour experience.
500 E Main Street, Louisville, KY 40202-1002
19
Barrels & Billets
Louisville, Kentucky·
4.0
(9) review
An exciting bourbon experience where guests can blend, create and bottle their very own bourbon. Guests will blend with six award-winning WoodCraft bourbons which includes a 200 Year Oak, European Oak, American Oak, Cherry Wood, Maple Wood, and Smoked Oak. During the experience, guests will learn the art of bourbon blending before the blending process begins. Once the blending experience is complete, guests can have their recipe bottled onsite.
800 W Main St, Louisville, KY 40202-2620
20
The Grill
Indianapolis, Indiana·
3.5
(9) review
9755 Fall Creek Rd, Indianapolis, IN 46256-4713
21
Smiley
Indianapolis, Indiana·
3.5
(9) review
Smiley is a huge 25,000 sq foot facility in Castleton filled with the latest Virtual Reality technology. We have very rare and unique interactive games and rides for children of all ages. Our playgrounds are for age 9 months to 10 years old and our VR spaces are for ages 9 years and up! We also have an enormous indoor playground with trampoline basketball, tubes & slides, rock-climbing, obstacle
5729 E 86th St, Indianapolis, IN 46250-1560
22
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
23
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.
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
24
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
25
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

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FAQ
Frequently Asked Questions
What's the driving distance between Leesburg and Chicago?
The distance is 1,113 miles
What's the travel time between Leesburg and Chicago?
The driving time can vary depending on traffic conditions, but it is typically 20h 48m mins in normal traffic
What are some of the best cities to visit between Leesburg and Chicago?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chicago?
There are plenty! Here are some stops you shouldn’t miss on your way to Chicago
What’s the weather like in Chicago?
The weather in Chicago is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chicago in January
Weather in Chicago in February
Weather in Chicago in March
Weather in Chicago in April
Weather in Chicago in May
Weather in Chicago in June
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Interested in a detailed plan for your time in Chicago?
Plan your dream Chicago trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Chicago
A 2-day itinerary in Chicago
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Where else can I travel to if I'm starting my trip in Leesburg?
We have a lot of great trip options for Leesburg! See the links below for all the itineraries we created for you