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By Huuk Team

Road trip from Chicago to Frederick

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iconFood & Drink
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Show more (4+)

ITINERARY

12h 13m654 miles17 stops
1
The Chopping Block
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
2
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.
3
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
4
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.
5
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
6
Lakeside Park & Rose Garden
1401 Lake Ave, Fort Wayne, IN 46805
7
Amherstburg Navy Yard National Historic Site
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
8
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)
9
Fish Point Nature Reserve
McCormick Rd, Ontario N0R 1M0 Canada
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
Museum of Contemporary Art Cleveland
11400 Euclid Ave, Cleveland, OH 44106-3926
13
Lock 3
200 S Main St, Akron, OH 44308-1315
14
Pittsburgh Water Steps
North Shore Riverfront Park, Pittsburgh, PA 15212
15
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.
16
Allegheny Cemetery
4734 Butler St, Pittsburgh, PA 15201-2951
Instituted in 1844, this 300-acre cemetery is the final resting place of such notables as Lillian Russell, Stephen Foster and General John Neville.
17
Cathedral of Learning
4200 5th Ave., Pittsburgh, PA 15260
Customize this Trip

OVERVIEW

Get ready for an epic adventure from the bustling city of Chicago to the charming town of Frederick! This journey will take you through diverse landscapes, from towering skyscrapers to rolling hills. Along the way, you'll discover hidden gems and create memories that will last a lifetime.

As you embark on this adventure, you'll witness the transformation of urban landscapes into tranquil countryside. The vibrant streets of Chicago will give way to serene farmlands, where the gentle breeze carries the scent of wildflowers. As you travel farther east, the rolling hills of Pennsylvania will greet you, a picturesque backdrop for your journey.

Throughout your adventure, you'll have the chance to explore historic landmarks, indulge in local cuisine, and connect with friendly locals. Whether you're seeking adventure or relaxation, this journey from Chicago to Frederick promises an unforgettable experience filled with discovery, wonder, and a touch of magic.

1
Start:The Chopping Block
Chicago, Illinois·
4.5
(98) review
The Chopping Block, Chicago's premiere recreational cooking school and gourmet retail store, offers demonstration and hands-on cooking classes, as well as wine classes, private cooking parties and corporate team building events. Classes at Lincoln Square cover subjects from cooking basics to intensive Boot Camps as well as seasonal, date nights, healthy and kids classes. We have a food-friendly wine selection so students can select beverages to pair with the menu of their class. Sorry, BYOB is not allowed.
4747 N Lincoln Ave Lincoln Square, Chicago, IL 60625-2026
2
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
3
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
4
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
5
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
6
Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
7
Amherstburg Navy Yard National Historic Site
Amherstburg, Ontario·
5.0
(94) review
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
8
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
9
Fish Point Nature Reserve
Pelee Island, Ontario·
4.5
(92) review
McCormick Rd, Ontario N0R 1M0 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
Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
13
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
14
Pittsburgh Water Steps
Pittsburgh, Pennsylvania·
4.5
(94) review
North Shore Riverfront Park, Pittsburgh, PA 15212
15
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
16
Allegheny Cemetery
Pittsburgh, Pennsylvania·
4.5
(94) review
Instituted in 1844, this 300-acre cemetery is the final resting place of such notables as Lillian Russell, Stephen Foster and General John Neville.
4734 Butler St, Pittsburgh, PA 15201-2951
17
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 Frederick?
The distance is 654 miles
What's the travel time between Chicago and Frederick?
The driving time can vary depending on traffic conditions, but it is typically 12h 13m mins in normal traffic
What are some of the best cities to visit between Chicago and Frederick?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Frederick?
There are plenty! Here are some stops you shouldn’t miss on your way to Frederick
What’s the weather like in Frederick?
The weather in Frederick is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Frederick in January
Weather in Frederick in February
Weather in Frederick in March
Weather in Frederick in April
Weather in Frederick in May
Weather in Frederick in June
Weather in Frederick in July
Weather in Frederick in August
Weather in Frederick in September
Weather in Frederick in October
Weather in Frederick in November
Weather in Frederick in December
Interested in a detailed plan for your time in Frederick?
Plan your dream Frederick trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Frederick
A 2-day itinerary in Frederick
A 3-day itinerary in Frederick
A 4-day itinerary in Frederick
A 5-day itinerary in Frederick
A 6-day itinerary in Frederick
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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