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By Huuk Team

Road trip from Chicago to Wilmington

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Show more (3+)

ITINERARY

17h 44m923 miles15 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
Arcade Legacy
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
4
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.
5
Iron Heart Winery
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
6
Game On Escapes & More
107 Edinburgh South Dr Suite 203, Cary, NC 27511-8426
We offer family friendly escape games and a game show appealing to a variety of ages. Great for corporate events, team outings, and just a fun night out with friends and family.
7
The Raleigh Market
1025 Blue Ridge Rd, Raleigh, NC 27607-3902
Located on the historic N.C. State Fairgrounds, The Raleigh Market is recognized as one of the Top 10 flea markets in the U.S. Each weekend, indoor and outdoor vendors showcase vintage goods and antiques, collectibles, new items, thrift items, crafts, art, jewelry and so much more. Food trucks, farm stands and fair food ensure customers do not leave hungry! The Raleigh Market is open Saturdays and Sundays, 9 am - 5 pm. Admission and parking are free.
8
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.
9
Crossgate Lanes
4230 Hunt Rd, Cincinnati, OH 45242-6612
10
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.
11
Ohio Stadium
411 Woody Hayes Dr,, Columbus, OH 43210-1104
12
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.
13
Grand 18-Winston-Salem
5601 University Pkwy, Winston Salem, NC 27105-1313
14
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.
15
Salem Lake
1001 Salem Lake Rd, Winston Salem, NC 27107-1571
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OVERVIEW

Picture yourself on an exciting journey from the bustling city of Chicago to the charming coastal town of Wilmington. Along the way, you'll witness a breathtaking tapestry of landscapes, from sprawling farmlands to shimmering rivers. The journey will take you through the heartland of America, where friendly faces and rich traditions await.

As you leave the Windy City behind, the towering skyscrapers will give way to rolling hills and serene farmlands. Watch as golden wheat fields sway in the breeze and gentle livestock graze peacefully in lush pastures. Cross meandering rivers and traverse rolling hills, where nature's beauty unfolds in all its splendor.

As you approach the Atlantic coast, the landscape transforms once more. The salty tang of the ocean fills the air as you pass through quaint towns with historic charm. The journey culminates in the picturesque destination of Wilmington, where sandy beaches, vibrant culture, and warm hospitality welcome you to a world of coastal delights.

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
Arcade Legacy
Cincinnati, Ohio·
4.5
(7) review
662 Cincinnati Mills Dr Inside the Mall at the Food Court, Cincinnati, OH 45240-1260
4
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
5
Iron Heart Winery
Allisonia, Virginia·
4.0
(7) review
3742 Boone Furnace Rd, Allisonia, VA 24347-4001
6
Game On Escapes & More
Cary, North Carolina·
5.0
(98) review
We offer family friendly escape games and a game show appealing to a variety of ages. Great for corporate events, team outings, and just a fun night out with friends and family.
107 Edinburgh South Dr Suite 203, Cary, NC 27511-8426
7
The Raleigh Market
Raleigh, North Carolina·
4.0
(96) review
Located on the historic N.C. State Fairgrounds, The Raleigh Market is recognized as one of the Top 10 flea markets in the U.S. Each weekend, indoor and outdoor vendors showcase vintage goods and antiques, collectibles, new items, thrift items, crafts, art, jewelry and so much more. Food trucks, farm stands and fair food ensure customers do not leave hungry! The Raleigh Market is open Saturdays and Sundays, 9 am - 5 pm. Admission and parking are free.
1025 Blue Ridge Rd, Raleigh, NC 27607-3902
8
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
9
Crossgate Lanes
Cincinnati, Ohio·
3.5
(7) review
4230 Hunt Rd, Cincinnati, OH 45242-6612
10
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
11
Ohio Stadium
Columbus, Ohio·
4.5
(979) review
411 Woody Hayes Dr,, Columbus, OH 43210-1104
12
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
13
Grand 18-Winston-Salem
Winston Salem, North Carolina·
4.0
(72) review
5601 University Pkwy, Winston Salem, NC 27105-1313
14
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
15
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 Wilmington?
The distance is 923 miles
What's the travel time between Chicago and Wilmington?
The driving time can vary depending on traffic conditions, but it is typically 17h 44m mins in normal traffic
What are some of the best cities to visit between Chicago and Wilmington?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Wilmington?
There are plenty! Here are some stops you shouldn’t miss on your way to Wilmington
What’s the weather like in Wilmington?
The weather in Wilmington is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Wilmington in January
Weather in Wilmington in February
Weather in Wilmington in March
Weather in Wilmington in April
Weather in Wilmington in May
Weather in Wilmington in June
Weather in Wilmington in July
Weather in Wilmington in August
Weather in Wilmington in September
Weather in Wilmington in October
Weather in Wilmington in November
Weather in Wilmington in December
Interested in a detailed plan for your time in Wilmington?
Plan your dream Wilmington trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Wilmington
A 2-day itinerary in Wilmington
A 3-day itinerary in Wilmington
A 4-day itinerary in Wilmington
A 5-day itinerary in Wilmington
A 6-day itinerary in Wilmington
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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