Road trip from New Bedford to Chicago
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Food & Drink
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Food & Drink
Fun & Games
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Museums
Shopping
Nightlife
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Nature & Parks
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ITINERARY
18h 51m992 miles22 stops
1
Jokers Wild Comedy Club
Jokers Wild has been providing laughs to Southern Connecticut since 2008. We bring some of the best and brightest names in comedy each and every week. Our comics appear on Letterman, Conan, Comedy Central, Last Comic Standing, Sirius/XM radio and tour all over the country. We take great pride in being the only authentic comedy club in Connecticut. We are a free standing comedy club that doesn't operate in a mall, casino or the back of a bar. Jokers Wild features a full bar, outdoor patio and an immaculate kitchen and we make it all happen on historic Wooster Street in New Haven.
2
New Haven Railroad Station
3
Yale University Art Gallery
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.
4
Steamtown National Historic Site
This small museum is all about steam engines and their contribution to America's economy in the 19th century.
5
Hollywood Gaming Mahoning Valley Race Course
6
Paladin Brewing
7
Lock 3
8
Rock & Roll Hall of Fame
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
Allen County War Memorial Coliseum
10
Bin 312 Wine Cellar
11
Rhode Island School of Design Museum of Art
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.
12
First Baptist Church in America
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.
13
Providence College
14
Broad Meadow Brook Conservation Center & Wildlife Sanctuary
Broad Meadow Brook in Worcester is the largest urban wildlife sanctuary in New England, with more than 400 acres cooperatively managed or owned by Mass Audubon. Interpretive signs will guide you along well-marked trails through woods, fields, streams, and marsh.
15
Cantor Art Gallery at Holy Cross
16
DCU Center
17
Annies Book Stop of Worcester
Annie's Book Stop of Worcester is the only general-reading independent book store in Worcester. We offer many genres of books, new and used, all at discounted prices. We also have gift items, audios, greeting cards and gift certificates. We also offer two to seven special events each week, from children's crafts to book signings to discussion groups. Our event guests are artists, authors & Celebs.
18
Dance Fitness Collaboration
Dance Fitness Collaboration is a boutique style fitness studio specializing in Zumba®, HIIT, Yoga, Reiki & Wellness. First time visit for a class is only $5; regular class drop-ins are $15 per class; other class packages, memberships and discounts available for viewing online.
19
Michigan Avenue Bridge
The view from the bridge is one of the best vistas the city has to offer.
20
The Chopping Block
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.
21
Boystown
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
22
Wrigley Field
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.
Customize this Trip
OVERVIEW
New Bedford to Chicago
1
Start:Jokers Wild Comedy Club
New Haven, Connecticut·
4.0
(9) review
Jokers Wild has been providing laughs to Southern Connecticut since 2008. We bring some of the best and brightest names in comedy each and every week. Our comics appear on Letterman, Conan, Comedy Central, Last Comic Standing, Sirius/XM radio and tour all over the country. We take great pride in being the only authentic comedy club in Connecticut. We are a free standing comedy club that doesn't operate in a mall, casino or the back of a bar. Jokers Wild features a full bar, outdoor patio and an immaculate kitchen and we make it all happen on historic Wooster Street in New Haven.
2
Start:New Haven Railroad Station
New Haven, Connecticut·
4.0
(97) review
50 Union Ave, New Haven, CT 06519-1754
3
Start: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.
4
Start: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.
5
Start:Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
6
Start:Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
7
Start:Lock 3
Akron, Ohio·
4.5
(98) review
200 S Main St, Akron, OH 44308-1315
8
Start: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
9
Start:Allen County War Memorial Coliseum
Fort Wayne, Indiana·
4.0
(99) review
4000 Parnell Ave, Fort Wayne, IN 46805-1414
10
Start:Bin 312 Wine Cellar
Providence, Rhode Island·
4.0
(9) review
312 S Main St, Providence, RI 02903-7118
11
Start: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.
12
Start: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.
13
Start:Providence College
Providence, Rhode Island·
4.5
(57) review
1 Cunningham Sq, Providence, RI 02918-7001
14
Start:Broad Meadow Brook Conservation Center & Wildlife Sanctuary
Worcester, Massachusetts·
4.5
(21) review
Broad Meadow Brook in Worcester is the largest urban wildlife sanctuary in New England, with more than 400 acres cooperatively managed or owned by Mass Audubon. Interpretive signs will guide you along well-marked trails through woods, fields, streams, and marsh.
15
Start:Cantor Art Gallery at Holy Cross
Worcester, Massachusetts·
4.5
(5) review
1 College St, Worcester, MA 01610-2322
16
Start:DCU Center
Worcester, Massachusetts·
3.5
(93) review
50 Foster Street, Worcester, MA 01608-1305
17
Start:Annies Book Stop of Worcester
Worcester, Massachusetts·
5.0
(5) review
Annie's Book Stop of Worcester is the only general-reading independent book store in Worcester. We offer many genres of books, new and used, all at discounted prices. We also have gift items, audios, greeting cards and gift certificates. We also offer two to seven special events each week, from children's crafts to book signings to discussion groups. Our event guests are artists, authors & Celebs.
18
Start:Dance Fitness Collaboration
Worcester, Massachusetts·
5.0
(3) review
Dance Fitness Collaboration is a boutique style fitness studio specializing in Zumba®, HIIT, Yoga, Reiki & Wellness. First time visit for a class is only $5; regular class drop-ins are $15 per class; other class packages, memberships and discounts available for viewing online.
19
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.
20
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.
21
Start: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
22
Start: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.
CHECKLIST
GPS device or app
Download Offline Map
Car charger and portable battery
Water bottles and snacks
Travel pillow and blanket
Sunglasses and sunscreen
First-aid kit
Trash bags
Hand sanitizer and wet wipes
Driver’s license and vehicle registration
Cash and cards
Camera or smartphone
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FAQ
Frequently Asked Questions
What's the driving distance between New Bedford and Chicago?
The distance is 992 miles
What's the travel time between New Bedford and Chicago?
The driving time can vary depending on traffic conditions, but it is typically 18h 51m mins in normal traffic
What are some of the best cities to visit between New Bedford and Chicago?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Chicago?
There are plenty! Here are some stops you shouldn’t miss on your way to Chicago
What’s the weather like in Chicago?
The weather in Chicago is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
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