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By Huuk Team

Road trip from Chicago to Lexington

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ITINERARY

7h 9m372 miles12 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
A. Philip Randolph Pullman Porter Museum
10406 S Maryland Ave Entrance 817 East 104th St from the parking lot, Chicago, IL 60628-3090
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
5
95th Street Bridge
3261 E 95th St between S Houston Ave. & South Avenue N, Chicago, IL 60617-5160
6
Calumet Park
9801 S Avenue G, Chicago, IL 60617-5537
7
DECEPTION
1 Carmichael Sq Carmel, Indianapolis, IN 46032
DECEPTION is a magic & mind reading show, hosted by magician David Ranalli. David creates an unforgettable evening by combining world-class sleight of hand, witty banter, and mysteries of the mind. Guests are invited into an intimate, cabaret theater where surprises lurk in every corner. Perfect as a date night, group event, and for the hardcore magic fan.
8
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.
9
Beckley Creek Park
1411 Beckley Creek Parkway, Louisville, KY 40245
10
Lexington Brewing & Distilling Co.
401 Cross St, Lexington, KY 40508-2806
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
11
Fayette Mall
3401 Nicholasville Rd, Lexington, KY 40503-3611
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
12
Waveland State Historic Site
225 Waveland Museum Ln, Lexington, KY 40514-1618
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
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OVERVIEW

This adventure begins in the bustling metropolis of Chicago, a city renowned for its towering skyscrapers, vibrant arts scene, and delectable deep-dish pizza. From there, we embark on a scenic journey through the heartland of America, traversing miles of rolling hills, picturesque farmland, and charming small towns. As we approach our destination, the landscape transforms into the rolling hills and lush greenery of Kentucky, a state steeped in history and natural beauty.

Our journey culminates in the historic city of Lexington, known as the "Horse Capital of the World." Here, we will delve into the rich equestrian heritage of the region, visit world-class horse farms, and witness the grace and athleticism of these magnificent animals. Beyond the equestrian allure, Lexington offers a vibrant downtown area, charming boutiques, and delectable local cuisine, ensuring a memorable and enriching experience for all who visit.

Throughout this adventure, we will uncover the hidden gems and iconic landmarks that define these two distinct regions of the United States. From the bustling streets of Chicago to the serene landscapes of Kentucky, this journey promises a tapestry of unforgettable experiences, creating lasting memories for travelers of all ages.

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
A. Philip Randolph Pullman Porter Museum
Chicago, Illinois·
3.5
(7) review
The National APR Pullman Porter Museum, is located in the National Park Service-Pullman National Monument. It is the only one of its kind world-wide. NAPRPPM is the first Black Labor History museum, in the United States, that exclusively tells the story of the Pullman Porters, The Brotherhood of Sleeping Car Porters labor union, and A. Philip Randolph Its founder. Tucked away on a quiet corner at the north end of Pullman National monument, don’t let the unassuming exterior keep you from missing this black heritage treasure. The museum presents, and interprets content intended to educate the public-on the impact the union had on organized labor, and on America’s modern day civil rights movement The exhibits chronicle the formation of the Brotherhood of Sleeping Car Porters; the first Black labor union in the United States chartered under the American Federation of Labor. Exhibits depict important activities on their amazing JOURNEY OF UNITY that ended in victory.
10406 S Maryland Ave Entrance 817 East 104th St from the parking lot, Chicago, IL 60628-3090
5
95th Street Bridge
Chicago, Illinois·
4.0
(4) review
3261 E 95th St between S Houston Ave. & South Avenue N, Chicago, IL 60617-5160
6
Calumet Park
Chicago, Illinois·
5.0
(7) review
9801 S Avenue G, Chicago, IL 60617-5537
7
DECEPTION
Indianapolis, Indiana·
4.5
(9) review
DECEPTION is a magic & mind reading show, hosted by magician David Ranalli. David creates an unforgettable evening by combining world-class sleight of hand, witty banter, and mysteries of the mind. Guests are invited into an intimate, cabaret theater where surprises lurk in every corner. Perfect as a date night, group event, and for the hardcore magic fan.
1 Carmichael Sq Carmel, Indianapolis, IN 46032
8
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
9
Beckley Creek Park
Louisville, Kentucky·
5.0
(70) review
1411 Beckley Creek Parkway, Louisville, KY 40245
10
Lexington Brewing & Distilling Co.
Lexington, Kentucky·
4.5
(984) review
The first era of the Lexington Brewing Co. began in the 1890s and came to a halt during Prohibition, changing ownership several times in the decades that followed. By the time Pearse Lyons and his son, Mark, explored the brewery in 1999, it was a dilapidated shell of what it had once been. However, Pearse was a visionary and entrepreneur and saw only what it could be. Spurred by a passion for brewing and distilling that courses through the Lyons family lineage of Irish coopers, Pearse revived Lexington Brewing Co. and restored a craft beer tradition that dates back to the 1700s. Pearse continued to dream big as he set his sights on distilling — a natural progression given his background in fermentation, his family’s heritage and Kentucky’s bourbon tradition. Two copper pot stills that were commissioned from Scotland arrived at Lexington Brewing Co. in 2008. In 2012, Town Branch Distillery opened, first new distillery to be built in Lexington, Kentucky, in more than 100 yrs.
401 Cross St, Lexington, KY 40508-2806
11
Fayette Mall
Lexington, Kentucky·
4.5
(91) review
Fayette Mall is located at the intersection of Nicholasville Road and Reynolds Road. The mall is central Kentucky’s premier shopping destination with over 170 retailer and dining options including The Disney Store, H&M, Michael Kors, Sephora and The Cheesecake Factory. Fayette Mall also features a children’s play area located in Center Court. Mobile device charging stations can be found in the Food Court. WiFi is available at Starbucks, Dillard’s and Dick’s Sporting Goods. Customer Service Center is located inside the front entrance next to P.F. Chang’s. Visit shopfayette-mall.com for more information including a complete list of retailers, restaurants, entertainment options and a mall map.
3401 Nicholasville Rd, Lexington, KY 40503-3611
12
Waveland State Historic Site
Lexington, Kentucky·
4.5
(97) review
Experience 19th century plantation life at this historic compound where you can tour the mansion or "big house," see quarters where slaves lived, visit a smokehouse and other elements of daily life in the Old South.
225 Waveland Museum Ln, Lexington, KY 40514-1618

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Lexington?
The distance is 372 miles
What's the travel time between Chicago and Lexington?
The driving time can vary depending on traffic conditions, but it is typically 7h 9m mins in normal traffic
What are some of the best cities to visit between Chicago and Lexington?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Lexington?
There are plenty! Here are some stops you shouldn’t miss on your way to Lexington
What’s the weather like in Lexington?
The weather in Lexington is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Lexington in January
Weather in Lexington in February
Weather in Lexington in March
Weather in Lexington in April
Weather in Lexington in May
Weather in Lexington in June
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Weather in Lexington in November
Weather in Lexington in December
Interested in a detailed plan for your time in Lexington?
Plan your dream Lexington trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Lexington
A 2-day itinerary in Lexington
A 3-day itinerary in Lexington
A 4-day itinerary in Lexington
A 5-day itinerary in Lexington
A 6-day itinerary in Lexington
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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