logo
By Huuk Team

Road trip from Chicago to Danbury

All Category
iconNature & Parks
iconFun & Games
iconSights & Landmarks
iconMuseums
iconFood & Drink
iconCasinos & Gambling
iconOutdoor Activities
Show more (3+)

ITINERARY

15h 37m835 miles22 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
Paladin Brewing
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
15
Hollywood Gaming Mahoning Valley Race Course
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
16
OH WOW! The Roger & Gloria Jones Children's Center for Science & Technology
15 Central Square First Floor, Youngstown, OH 44503
OH WOW!TM’s colorful, hands-on environment encourages independent thinking through interactive STEM-based exhibits and EDUtaining programs.”
17
Basilica of Our Lady of Mount Carmel
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
18
West End - Elliot Overlook Park
599 Fairview Rd At the end of Fairview AVE and alos Marlow @ Rue Grande Vue St 40°26'44.4N 80°02'02.6W, Pittsburgh, PA 15205
19
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.
20
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.
21
Marine Corps League NE Detachment Museum
1340 Alder Street, Scranton, PA
22
Everhart Museum
1901 Mulberry St, Scranton, PA 18510-2390
Customize this Trip

OVERVIEW

Embark on an exciting road trip from the bustling metropolis of Chicago to the charming city of Danbury, a journey that promises a perfect blend of urban adventures and serene escapes. As you traverse the 980-mile expanse, you'll encounter diverse landscapes, delve into rich histories, and create memories that will last a lifetime.

Along the way, you'll pass through the rolling hills and lush greenery of Indiana, where you can explore the serene beauty of Amish country. The vibrant cities of Ohio and Pennsylvania will captivate you with their cultural attractions, museums, and historical landmarks. As you approach Danbury, the scenery transforms into a picturesque mosaic of rolling hills, sparkling lakes, and quaint New England towns.

Whether you're seeking adventure, relaxation, or a combination of both, this road trip offers something for every traveler. Immerse yourself in the vibrant energy of Chicago, discover the hidden gems of small towns, and embrace the tranquility of the countryside. Along the way, you'll encounter friendly locals, savor delicious cuisine, and witness the beauty of the American Midwest and Northeast.

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
Paladin Brewing
Austintown, Youngstown, Ohio·
4.5
(9) review
6520 Mahoning Ave, Austintown, Youngstown, OH 44515-2012
15
Hollywood Gaming Mahoning Valley Race Course
Youngstown, Ohio·
3.5
(83) review
655 N Canfield Niles Rd, Youngstown, OH 44515-1102
16
OH WOW! The Roger & Gloria Jones Children's Center for Science & Technology
Youngstown, Ohio·
4.5
(62) review
OH WOW!TM’s colorful, hands-on environment encourages independent thinking through interactive STEM-based exhibits and EDUtaining programs.”
15 Central Square First Floor, Youngstown, OH 44503
17
Basilica of Our Lady of Mount Carmel
Youngstown, Ohio·
4.5
(7) review
343 Via Mount Carmel Ave, Youngstown, OH 44505-3037
18
West End - Elliot Overlook Park
Pittsburgh, Pennsylvania·
4.5
(70) review
599 Fairview Rd At the end of Fairview AVE and alos Marlow @ Rue Grande Vue St 40°26'44.4N 80°02'02.6W, Pittsburgh, PA 15205
19
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
20
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
21
Marine Corps League NE Detachment Museum
Scranton, Pennsylvania·
5.0
(8) review
1340 Alder Street, Scranton, PA
22
Everhart Museum
Scranton, Pennsylvania·
4.0
(76) review
1901 Mulberry St, Scranton, PA 18510-2390

CHECKLIST

icon
GPS device or app
icon
Download Offline Map
icon
Car charger and portable battery
icon
Water bottles and snacks
icon
Travel pillow and blanket
icon
Sunglasses and sunscreen
icon
First-aid kit
icon
Trash bags
icon
Hand sanitizer and wet wipes
icon
Driver’s license and vehicle registration
icon
Cash and cards
icon
Camera or smartphone
Unlock Effortless Travel Planning
Create your dream trip in minutes by this prompt. Try now!
FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Danbury?
The distance is 835 miles
What's the travel time between Chicago and Danbury?
The driving time can vary depending on traffic conditions, but it is typically 15h 37m mins in normal traffic
What are some of the best cities to visit between Chicago and Danbury?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Danbury?
There are plenty! Here are some stops you shouldn’t miss on your way to Danbury
What’s the weather like in Danbury?
The weather in Danbury is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Danbury in January
Weather in Danbury in February
Weather in Danbury in March
Weather in Danbury in April
Weather in Danbury in May
Weather in Danbury in June
Weather in Danbury in July
Weather in Danbury in August
Weather in Danbury in September
Weather in Danbury in October
Weather in Danbury in November
Weather in Danbury in December
Interested in a detailed plan for your time in Danbury?
Plan your dream Danbury trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Danbury
A 2-day itinerary in Danbury
A 3-day itinerary in Danbury
A 4-day itinerary in Danbury
A 5-day itinerary in Danbury
A 6-day itinerary in Danbury
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
logo
Features
Roadtrip PlanBlogAI Agent for TravelNear byFeedback
About
About HuukPolicyTermsPrivacy
Contact us
DiscordFacebookTiktokInstagramYoutubeLinkedin