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By Huuk Team

Road trip from Chicago to Worcester

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Show more (4+)

ITINERARY

18h 2m955 miles27 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
Allen County War Memorial Coliseum
4000 Parnell Ave, Fort Wayne, IN 46805-1414
5
Lakeside Park & Rose Garden
1401 Lake Ave, Fort Wayne, IN 46805
6
Amherstburg Navy Yard National Historic Site
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
7
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)
8
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
9
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.
10
Museum of Contemporary Art Cleveland
11400 Euclid Ave, Cleveland, OH 44106-3926
11
Lock 3
200 S Main St, Akron, OH 44308-1315
12
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
13
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
14
Basilica of Our Lady of Mount Carmel
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
15
ScareHouse
461 Pittsburgh Mills Cir, Pittsburgh, PA 15084-3833
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
16
Steamtown National Historic Site
350 Cliff St, Scranton, PA 18503
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
17
Marine Corps League NE Detachment Museum
1340 Alder Street, Scranton, PA
18
Yale University Art Gallery
1111 Chapel Street, New Haven, CT 06510-2301
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
19
Owl Shop Cigar Lounge
268 College St, New Haven, CT 06510-2404
20
David S. Ingalls Rink
73 Sachem St, New Haven, CT 06511-3518
21
New Haven Railroad Station
50 Union Ave, New Haven, CT 06519-1754
22
Burnside Fountain
Main St Behind City Hall, Worcester, MA 01608-1821
23
DCU Center
50 Foster Street, Worcester, MA 01608-1305
24
Seed To Stem
174 Shrewsbury St, Worcester, MA 01604-4629
25
Redemption Rock Brewing Co.
333 Shrewsbury St Entrance on Putnam Ln., Worcester, MA 01604-4614
Redemption Rock Brewing Co. is a craft brewery, taproom, and cafe in Worcester, Mass. We make beer for people. "Beer for people" means beer enjoyed with a strong sense of community and camaraderie, and we aim to provide high-quality, fun beer in all its forms. Also, as a certified Benefit Corporation (B Corp), we’re dedicated to working for the community. It’s an essential part of our business, and we’re continually looking for new ways to support local organizations, partner with local businesses, and be a better kind of employer and corporate citizen. Finally, we’ve designed the Redemption Rock taproom to be the ultimate community gathering space. It’s bright, comfortable, and colorful and serves as both a coffeehouse and a bar. Visit us with your friends, come meet new friends, or even hold your private event here. We hope to see you soon.
26
First Baptist Church in America
75 N Main St, Providence, RI 02903-1307
The oldest Baptist church in America, gathered by Roger Williams in 1638. Open for tours: Monday - Friday 10AM - Noon and 1PM - 3PM and on Sunday immediately following the Worship Service Worship Service is at 11 AM September - May and at 10 AM June, July and August.
27
Rhode Island School of Design Museum of Art
224 Benefit St, Providence, RI 02903-2711
This innovative and internationally renowned museum showcases more than 80,000 works of art from Paul Revere's silver and caricatures of 18th century Europe, to French Impressionists and the avant-garde works of recent alumni. A 12th-century Japanese Buddha has its own room with benches for meditating.
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OVERVIEW

Get ready for an exciting adventure as we embark on a road trip from the bustling city of Chicago to the historic town of Worcester. Along the way, we'll traverse a distance of over 1,000 miles, passing through a diverse tapestry of landscapes and vibrant cities.

Our journey will take us across the vast expanse of the Midwest, where we'll marvel at rolling farmlands and picturesque towns. We'll navigate the winding roads of Indiana and Ohio, soaking in the charm of cozy communities and historic landmarks. As we approach New England, the scenery transforms into rolling hills and lush forests, setting the stage for our arrival in the charming town of Worcester.

Throughout our adventure, we'll have ample opportunities to explore hidden gems, savor local flavors, and create unforgettable memories. Whether it's discovering the vibrant cultural scene of a city, immersing ourselves in the tranquility of nature, or simply enjoying the camaraderie of our fellow travelers, this road trip promises a wealth of experiences that will enrich our minds and hearts.

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
Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
5
Lakeside Park & Rose Garden
Fort Wayne, Indiana·
4.5
(96) review
1401 Lake Ave, Fort Wayne, IN 46805
6
Amherstburg Navy Yard National Historic Site
Amherstburg, Ontario·
5.0
(94) review
Dalhousie Street, Amherstburg, Ontario N9V 1W7 Canada
7
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
8
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
9
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
10
Museum of Contemporary Art Cleveland
Cleveland, Ohio·
3.5
(93) review
11400 Euclid Ave, Cleveland, OH 44106-3926
11
Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
12
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
13
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
14
Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
15
ScareHouse
Pittsburgh, Pennsylvania·
4.0
(87) review
Pittsburgh Zombies love shopping malls – and we think you will love our NEW, larger, and permanent home inside the Galleria at Pittsburgh Mills. Thank You Pittsburgh for supporting us for more than 20 years of fears! ScareHouse has been ranked as one of “America’s Scariest Halloween Attractions” by Travel Channel and has been featured on Good Morning America, USA TODAY, The Daily Show and many other national media outlets.
461 Pittsburgh Mills Cir, Pittsburgh, PA 15084-3833
16
Steamtown National Historic Site
Scranton, Pennsylvania·
4.5
(902) review
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
350 Cliff St, Scranton, PA 18503
17
Marine Corps League NE Detachment Museum
Scranton, Pennsylvania·
5.0
(8) review
1340 Alder Street, Scranton, PA
18
Yale University Art Gallery
New Haven, Connecticut·
5.0
(984) review
Yale University Art Gallery is the oldest college art museum in America. The Gallery’s encyclopedic holdings of more than 250,000 objects range from ancient times to the present day and represent civilizations from around the globe. Spanning a block and a half of the city of New Haven, Connecticut, the Gallery comprises three architecturally distinct buildings, including a masterpiece of modern architecture from 1953 designed by Louis Kahn through which visitors enter. The museum is free and open to the public.
1111 Chapel Street, New Haven, CT 06510-2301
19
Owl Shop Cigar Lounge
New Haven, Connecticut·
4.5
(9) review
268 College St, New Haven, CT 06510-2404
20
David S. Ingalls Rink
New Haven, Connecticut·
4.5
(9) review
73 Sachem St, New Haven, CT 06511-3518
21
New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
22
Burnside Fountain
Worcester, Massachusetts·
3.5
(8) review
Main St Behind City Hall, Worcester, MA 01608-1821
23
DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
24
Seed To Stem
Worcester, Massachusetts·
4.0
(9) review
174 Shrewsbury St, Worcester, MA 01604-4629
25
Redemption Rock Brewing Co.
Worcester, Massachusetts·
5.0
(9) review
Redemption Rock Brewing Co. is a craft brewery, taproom, and cafe in Worcester, Mass. We make beer for people. "Beer for people" means beer enjoyed with a strong sense of community and camaraderie, and we aim to provide high-quality, fun beer in all its forms. Also, as a certified Benefit Corporation (B Corp), we’re dedicated to working for the community. It’s an essential part of our business, and we’re continually looking for new ways to support local organizations, partner with local businesses, and be a better kind of employer and corporate citizen. Finally, we’ve designed the Redemption Rock taproom to be the ultimate community gathering space. It’s bright, comfortable, and colorful and serves as both a coffeehouse and a bar. Visit us with your friends, come meet new friends, or even hold your private event here. We hope to see you soon.
333 Shrewsbury St Entrance on Putnam Ln., Worcester, MA 01604-4614
26
First Baptist Church in America
Providence, Rhode Island·
4.5
(91) review
The oldest Baptist church in America, gathered by Roger Williams in 1638. Open for tours: Monday - Friday 10AM - Noon and 1PM - 3PM and on Sunday immediately following the Worship Service Worship Service is at 11 AM September - May and at 10 AM June, July and August.
75 N Main St, Providence, RI 02903-1307
27
Rhode Island School of Design Museum of Art
Providence, Rhode Island·
4.5
(981) review
This innovative and internationally renowned museum showcases more than 80,000 works of art from Paul Revere's silver and caricatures of 18th century Europe, to French Impressionists and the avant-garde works of recent alumni. A 12th-century Japanese Buddha has its own room with benches for meditating.
224 Benefit St, Providence, RI 02903-2711

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Worcester?
The distance is 955 miles
What's the travel time between Chicago and Worcester?
The driving time can vary depending on traffic conditions, but it is typically 18h 2m mins in normal traffic
What are some of the best cities to visit between Chicago and Worcester?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Worcester?
There are plenty! Here are some stops you shouldn’t miss on your way to Worcester
What’s the weather like in Worcester?
The weather in Worcester is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Worcester in January
Weather in Worcester in February
Weather in Worcester in March
Weather in Worcester in April
Weather in Worcester in May
Weather in Worcester in June
Weather in Worcester in July
Weather in Worcester in August
Weather in Worcester in September
Weather in Worcester in October
Weather in Worcester in November
Weather in Worcester in December
Interested in a detailed plan for your time in Worcester?
Plan your dream Worcester trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Worcester
A 2-day itinerary in Worcester
A 3-day itinerary in Worcester
A 4-day itinerary in Worcester
A 5-day itinerary in Worcester
A 6-day itinerary in Worcester
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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