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By Huuk Team

Road trip from Chicago to Chesapeake

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ITINERARY

16h 56m881 miles14 stops
1
Fort Ward Museum & Historic Site
4301 W Braddock Rd, Alexandria, VA 22304-1007
2
The Mariners' Museum and Park
100 Museum Drive, Newport News, VA 23606
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
3
O'Connor Brewing Co.
211 W 24th St, Norfolk, VA 23517
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
4
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.
5
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
6
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.
7
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
8
Lakeside Park & Rose Garden
1401 Lake Ave, Fort Wayne, IN 46805
9
Sprucewood Shores Estate Winery
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
10
Rock & Roll Hall of Fame
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
11
Federal Reserve Bank of Cleveland: Education and Learning Center
1455 E 6th St, Cleveland, OH 44114-2517
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
12
Lock 3
200 S Main St, Akron, OH 44308-1315
13
Point State Park
601 Commonwealth Pl Bldg A, Pittsburgh, PA 15222
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
14
Cathedral of Learning
4200 5th Ave., Pittsburgh, PA 15260
Customize this Trip

OVERVIEW

Imagine setting sail on an unforgettable adventure that spans the vastness of the Midwest and the allure of the East Coast. Our voyage begins in the bustling metropolis of Chicago, where the iconic skyline serves as our backdrop. As we embark on our journey, the shimmering waters of the Great Lakes guide our path, leading us through picturesque canals and under majestic bridges.

Along the way, we'll witness the serene beauty of rolling hills and sprawling countryside, where nature's tapestry unfolds before our eyes. Quaint towns and hidden gems beckon us to explore, each with its own unique charm and stories to tell. The rhythm of life slows down as we navigate the tranquil waters, allowing us to reconnect with ourselves and the world around us.

Our destination awaits in the heart of the Chesapeake Bay, a vibrant ecosystem teeming with wildlife and maritime history. As we approach our final port, the air fills with the salty tang of the sea, promising new adventures and unforgettable memories. Along the way, we'll have the opportunity to witness breathtaking sunsets, marvel at the grandeur of nature, and create lasting connections with fellow travelers. Our journey from Chicago to Chesapeake is not just a trip; it's an extraordinary experience that will leave an enduring mark on our hearts and minds.

1
Start:Fort Ward Museum & Historic Site
Alexandria, Virginia·
4.0
(71) review
4301 W Braddock Rd, Alexandria, VA 22304-1007
2
The Mariners' Museum and Park
Newport News, Virginia·
5.0
(959) review
Curate your Mariners’ Experience! From inspiring stories of mariners who risked it all for freedom to true tales of man conquering the wild seas, our indoor galleries will spark curiosity, wonder, and an appreciation for our shared maritime heritage. Explore over 90,000 square feet of gallery space and discover your connection to our shared maritime heritage. Admission to the Museum is only $1 per person. Add some outdoor adventure to your day in our 550-acre Park which offers visitors a quiet and serene place to walk, hike or run amongst rolling woodlands. Our Park features the award-winning five-mile Noland Trail that surrounds the 167-acre Mariners’ Lake. The Park is free and open to the public.
100 Museum Drive, Newport News, VA 23606
3
O'Connor Brewing Co.
Norfolk, Virginia·
4.5
(97) review
The brewery is located at 211 W. 24th Street in the new Railroad district of Norfolk, situated next to the historic Ghent neighborshood and just a mile or two from Downtown. The Tasting Room and Production facility share a 35,000 sq. foot mid-century modern historic building. Free parking is available in their private lot or street parking is free along 24th and 23rd street. O’Connor beer drinkers come from all walks of life, but what brings them together is a love of the small, simple joys in life. The pleasure of being outdoors, relaxing on the beach with friends, having dinner with family after a day of hard work, and of course, enjoying a fresh, flavorful beer. Customers appreciate the O’Connor brand for its approachability and authenticity. They value its independent spirit, that it remains family owned and operated, and its support of the local community. And their loyalty has established it as a mainstay brand with 10 years of sustained success.
211 W 24th St, Norfolk, VA 23517
4
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
5
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
6
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
7
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
8
Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
9
Sprucewood Shores Estate Winery
Harrow, Essex, Ontario·
4.5
(97) review
The Sprucewood Family warmly welcomes you to sample handcrafted 100% Ontario VQA wines at Ontario's only beachfront destination vineyard, winery and tasting room. We are situated on 45 Acres with access to gardens, a sandy beach, and picnic tables. Enjoy a glass of wine with a picnic basket and explore our grounds year round. Tasting room open 7 days a week 11am - 5pm (we occasionally close early due to special events. Please check our social media for daily updates @sprucewoodshores)
7258 Cty Rd, 50 West, Harrow, Essex, Ontario N0R 1G0 Canada
10
Rock & Roll Hall of Fame
Cleveland, Ohio·
4.5
(9964) review
Headquartered in a boldly designed building on Lake Erie's shore, The Rock and Roll Hall of Fame is a 150,000-square-foot museum featuring ever-changing exhibits documenting the history of rock and roll, from Elvis to our days. You’ll see hundreds of original artifacts, from Jimi Hendrix outfits to The Beatles’ handwritten lyrics. Experience the excitement of a Rock Hall induction night at the Power of Rock Experience or have your very own jam session at the Garage. You can also watch a concert while you're here, so check out the Rock Hall’s schedule and plan ahead. – Tripadvisor
1100 Rock and Roll Blvd Main Terminal, Cleveland, OH 44114-1023
11
Federal Reserve Bank of Cleveland: Education and Learning Center
Cleveland, Ohio·
4.5
(95) review
Ever wonder how money works or what the Federal Reserve Bank of Cleveland does as part of the central bank of the US? Visit our Education and Learning Center featuring more than 25 fun, hands-on exhibits that answer these questions and more! We have interactive games, visual exhibits, creative stations, and illuminating films that explain everything about money you can think of, from how we use it, to why it looks the way it looks. Come see our historic lobby, take pictures with our money tree, trade coconuts on Barter Island, identify counterfeit bills, and even make your own money! All this in the heart of Cleveland, just steps away from downtown attractions. Admission is free and photos are welcome.
1455 E 6th St, Cleveland, OH 44114-2517
12
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
13
Point State Park
Pittsburgh, Pennsylvania·
4.5
(951) review
Serving as a key strategic spot during the French and Indian War, this National Historic Landmark and park offer stunning views of the city and a variety of outdoor recreation.
601 Commonwealth Pl Bldg A, Pittsburgh, PA 15222
14
Cathedral of Learning
Pittsburgh, Pennsylvania·
4.5
(979) review
4200 5th Ave., Pittsburgh, PA 15260

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Chesapeake?
The distance is 881 miles
What's the travel time between Chicago and Chesapeake?
The driving time can vary depending on traffic conditions, but it is typically 16h 56m mins in normal traffic
What are some of the best cities to visit between Chicago and Chesapeake?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chesapeake?
There are plenty! Here are some stops you shouldn’t miss on your way to Chesapeake
What’s the weather like in Chesapeake?
The weather in Chesapeake is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Chesapeake in January
Weather in Chesapeake in February
Weather in Chesapeake in March
Weather in Chesapeake in April
Weather in Chesapeake in May
Weather in Chesapeake in June
Weather in Chesapeake in July
Weather in Chesapeake in August
Weather in Chesapeake in September
Weather in Chesapeake in October
Weather in Chesapeake in November
Weather in Chesapeake in December
Interested in a detailed plan for your time in Chesapeake?
Plan your dream Chesapeake trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Chesapeake
A 2-day itinerary in Chesapeake
A 3-day itinerary in Chesapeake
A 4-day itinerary in Chesapeake
A 5-day itinerary in Chesapeake
A 6-day itinerary in Chesapeake
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