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By Huuk Team

Road trip from Chicago to Greensboro

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ITINERARY

13h 57m720 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
Howard Schrott Center for the Arts
610 W 46th St, Indianapolis, IN 46208-3642
5
Arcade Legacy
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
6
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.
7
Crossgate Lanes
4230 Hunt Rd, Cincinnati, OH 45242-6612
8
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.
9
Iron Heart Winery
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
10
Grand 18-Winston-Salem
5601 University Pkwy, Winston Salem, NC 27105-1313
11
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.
12
Salem Lake
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
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OVERVIEW

Get ready for an exciting adventure as we embark on a thrilling road trip from the vibrant city of Chicago to the charming town of Greensboro. Along the way, we'll explore diverse landscapes, encounter fascinating people, and create memories that will last a lifetime.

Our journey will take us through rolling hills, lush forests, and bustling cities. We'll discover hidden gems, immerse ourselves in local cultures, and savor the unique flavors of each region. From the towering skyscrapers of Chicago to the historic streets of Greensboro, every stop along the way promises a new adventure.

As we travel, we'll share stories, sing songs, and play games to make the time fly by. We'll embrace the unexpected, embrace new experiences, and learn from the diverse perspectives of those we meet. So buckle up, get ready for an unforgettable road trip that will leave an imprint on your heart and mind.

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
Howard Schrott Center for the Arts
Indianapolis, Indiana·
5.0
(1) review
610 W 46th St, Indianapolis, IN 46208-3642
5
Arcade Legacy
Cincinnati, Ohio·
4.5
(7) review
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
6
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
7
Crossgate Lanes
Cincinnati, Ohio·
3.5
(7) review
4230 Hunt Rd, Cincinnati, OH 45242-6612
8
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
9
Iron Heart Winery
Allisonia, Virginia·
4.0
(7) review
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
10
Grand 18-Winston-Salem
Winston Salem, North Carolina·
4.0
(72) review
5601 University Pkwy, Winston Salem, NC 27105-1313
11
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
12
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 Greensboro?
The distance is 720 miles
What's the travel time between Chicago and Greensboro?
The driving time can vary depending on traffic conditions, but it is typically 13h 57m mins in normal traffic
What are some of the best cities to visit between Chicago and Greensboro?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Greensboro?
There are plenty! Here are some stops you shouldn’t miss on your way to Greensboro
What’s the weather like in Greensboro?
The weather in Greensboro is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Greensboro in January
Weather in Greensboro in February
Weather in Greensboro in March
Weather in Greensboro in April
Weather in Greensboro in May
Weather in Greensboro in June
Weather in Greensboro in July
Weather in Greensboro in August
Weather in Greensboro in September
Weather in Greensboro in October
Weather in Greensboro in November
Weather in Greensboro in December
Interested in a detailed plan for your time in Greensboro?
Plan your dream Greensboro trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Greensboro
A 2-day itinerary in Greensboro
A 3-day itinerary in Greensboro
A 4-day itinerary in Greensboro
A 5-day itinerary in Greensboro
A 6-day itinerary in Greensboro
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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