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By Huuk Team

Road trip from Chicago to Winston-Salem

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ITINERARY

13h 27m694 miles13 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
Arcade Legacy
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
5
Archery Arena (Dodgeball Archery)
4950 Provident Dr, Cincinnati, OH 45246-1021
Archery Arena is the first and only dedicated Combat Archery facility in Cincinnati. Think dodgeball with specially made bows and arrows. Battle it out with friends, co-workers, and strangers! Strategize and win! It’s a fun, safe, and addicting sport that gets progressively more intense at the session progresses. Book individual tickets or come as group. Great Team Building Activity.
6
Crossgate Lanes
4230 Hunt Rd, Cincinnati, OH 45242-6612
7
Painted Tree Boutiques - Cincinnati
11315 Montgomery Rd, Cincinnati, OH 45249
A creative community of thousands of shop owners and locations across the nation, Painted Tree Boutiques is a shopping experience like no other. Find gifts, decor, fashion, and more with hundreds of local shops all under one roof.
8
Ohio Stadium
411 Woody Hayes Dr,, Columbus, OH 43210-1104
9
Kelton House Museum & Garden
586 E Town St, Columbus, OH 43215-4802
Experience urban life and the decorative arts, as they existed in the second half of the 19th century, through the collection of the Sophia and Fernando Cortez Kelton family. Learn about the Underground Railroad and the people that bring the history to life.
10
Iron Heart Winery
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
11
Grand 18-Winston-Salem
5601 University Pkwy, Winston Salem, NC 27105-1313
12
Lam Museum of Anthropology, Wake Forest University
Palmer Hall, Carroll Weathers Drive, Winston Salem, NC 27109
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
13
Salem Lake
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
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OVERVIEW

Get ready for an epic adventure as we embark on an exciting journey from the bustling city of Chicago to the charming town of Winston-Salem! Along the way, we'll discover hidden gems, encounter friendly locals, and create memories that will last a lifetime. The journey unfolds like a captivating storybook, offering a blend of urban adventures and scenic escapes. From exploring world-renowned museums to marveling at breathtaking landscapes, this road trip promises an unforgettable experience.

Our adventure begins in the vibrant heart of Chicago, where towering skyscrapers and bustling streets paint a picture of modern city life. We'll immerse ourselves in the city's rich culture, visiting iconic landmarks and indulging in its diverse culinary scene. As we venture further, the landscape transforms into rolling hills and lush greenery, leading us to charming towns and quaint villages. We'll stop at cozy cafes, meet welcoming locals, and uncover the hidden stories that make each place unique.

As we approach our destination, Winston-Salem welcomes us with open arms. This historic town seamlessly blends its rich Moravian heritage with modern-day attractions. We'll explore historic buildings, immerse ourselves in local arts and crafts, and savor the flavors of Southern cuisine. The journey from Chicago to Winston-Salem is not merely a road trip; it's an adventure that connects us to the heart of America, revealing the beauty and diversity that lies within.

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
Arcade Legacy
Cincinnati, Ohio·
4.5
(7) review
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
5
Archery Arena (Dodgeball Archery)
Cincinnati, Ohio·
5.0
(36) review
Archery Arena is the first and only dedicated Combat Archery facility in Cincinnati. Think dodgeball with specially made bows and arrows. Battle it out with friends, co-workers, and strangers! Strategize and win! It’s a fun, safe, and addicting sport that gets progressively more intense at the session progresses. Book individual tickets or come as group. Great Team Building Activity.
4950 Provident Dr, Cincinnati, OH 45246-1021
6
Crossgate Lanes
Cincinnati, Ohio·
3.5
(7) review
4230 Hunt Rd, Cincinnati, OH 45242-6612
7
Painted Tree Boutiques - Cincinnati
Cincinnati, Ohio·
5.0
(6) review
A creative community of thousands of shop owners and locations across the nation, Painted Tree Boutiques is a shopping experience like no other. Find gifts, decor, fashion, and more with hundreds of local shops all under one roof.
11315 Montgomery Rd, Cincinnati, OH 45249
8
Ohio Stadium
Columbus, Ohio·
4.5
(979) review
411 Woody Hayes Dr,, Columbus, OH 43210-1104
9
Kelton House Museum & Garden
Columbus, Ohio·
4.5
(96) review
Experience urban life and the decorative arts, as they existed in the second half of the 19th century, through the collection of the Sophia and Fernando Cortez Kelton family. Learn about the Underground Railroad and the people that bring the history to life.
586 E Town St, Columbus, OH 43215-4802
10
Iron Heart Winery
Allisonia, Virginia·
4.0
(7) review
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
11
Grand 18-Winston-Salem
Winston Salem, North Carolina·
4.0
(72) review
5601 University Pkwy, Winston Salem, NC 27105-1313
12
Lam Museum of Anthropology, Wake Forest University
Winston Salem, North Carolina·
4.0
(9) review
Discover North Carolina's only museum dedicated to the study of global cultures. Explore stories of humanity, from ancient archaeological sites to the celebrations and struggles of today. Learn about peoples around the world through their everyday and ceremonial objects, and visual arts. Changing exhibits highlight the Museum's collections of nearly 30,000 archaeological and ethnographic artifacts from more than 350 cultures and 90 countries. Admission is free.
Palmer Hall, Carroll Weathers Drive, Winston Salem, NC 27109
13
Salem Lake
Winston Salem, North Carolina·
4.5
(97) review
1001 Salem Lake Rd, Winston Salem, NC 27107-1571

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Winston-Salem?
The distance is 694 miles
What's the travel time between Chicago and Winston-Salem?
The driving time can vary depending on traffic conditions, but it is typically 13h 27m mins in normal traffic
What are some of the best cities to visit between Chicago and Winston-Salem?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Winston-Salem?
There are plenty! Here are some stops you shouldn’t miss on your way to Winston-Salem
What’s the weather like in Winston-Salem?
The weather in Winston-Salem is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Winston-Salem in January
Weather in Winston-Salem in February
Weather in Winston-Salem in March
Weather in Winston-Salem in April
Weather in Winston-Salem in May
Weather in Winston-Salem in June
Weather in Winston-Salem in July
Weather in Winston-Salem in August
Weather in Winston-Salem in September
Weather in Winston-Salem in October
Weather in Winston-Salem in November
Weather in Winston-Salem in December
Interested in a detailed plan for your time in Winston-Salem?
Plan your dream Winston-Salem trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Winston-Salem
A 2-day itinerary in Winston-Salem
A 3-day itinerary in Winston-Salem
A 4-day itinerary in Winston-Salem
A 5-day itinerary in Winston-Salem
A 6-day itinerary in Winston-Salem
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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