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By Huuk Team

Road trip from Chicago to Ann Arbor

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ITINERARY

4h 38m241 miles12 stops
1
Museum Of Illusions Chicago
25 E Washington St, Chicago, IL 60602-1708
2
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.
3
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.
4
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
5
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.
6
Confections with Convictions
116 W Crosstown Pkwy, Kalamazoo, MI 49001-2732
Kalamazoo's only shop making hand crafted truffles and other confections exclusively from Fair Trade, organic certified chocolate. Chocolatier Dale Anderson's original recipes contain fresh local fruits, honey, and maple syrup. Vegan and gluten free options are always available. Closed Sunday and Monday. Open Tuesday thru Saturday 10 a.m. until 6:00 p.m.
7
River Trail
Lansing, MI 48912 ‎
8
Hudson Mills Metropark
8801 N Territorial Rd, Ann Arbor, MI 48130-9626
1,549-acre Park Has An 18-hole Golf Course.
9
The Ark
316 S Main St, Ann Arbor, MI 48104-2108
This music venue and nonprofit organization is dedicated to the presentation and encouragement of folk, roots and ethnic music through live performances by well-known and up-and-coming entertainers.
10
Kelsey Museum of Archaeology
University of Michigan 434 South State Street, Ann Arbor, MI 48109
The Kelsey Museum houses a collection of nearly 100,000 objects from the civilizations of the Mediterranean.
11
Furstenberg Nature Area
Fuller Road Opposite Huron High School, Ann Arbor, MI 48105
12
Decode Ann Arbor
3170 Packard St, Ann Arbor, MI 48108
Discover adventures for teams large and small! Our award-winning escape rooms at Decode Ann Arbor take you around the globe and to destinations beyond your wildest imagination. Bring you friends and family and join in the fun!
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OVERVIEW

Calling all adventure seekers! Get ready for an unforgettable journey from the vibrant city of Chicago to the charming college town of Ann Arbor. This Midwest adventure promises a captivating blend of urban exploration and collegiate vibes, creating memories that will last a lifetime.

As you embark on your journey, marvel at the towering skyscrapers and bustling streets of Chicago, a city that pulsates with energy and cultural experiences. Immerse yourself in the city's world-class museums, explore its diverse neighborhoods, and indulge in its culinary delights. But don't get too comfortable, because the adventure doesn't stop there.

Venture into the heart of Ann Arbor, a picturesque town that exudes academic charm and youthful energy. Stroll through the historic streets, admire the Gothic architecture of the University of Michigan campus, and soak in the vibrant atmosphere of this college town. From exploring hands-on museums to catching a thrilling football game, Ann Arbor offers endless opportunities to engage, learn, and create memories that will last a lifetime.

1
Start:Museum Of Illusions Chicago
Chicago, Illinois·
4.5
(97) review
25 E Washington St, Chicago, IL 60602-1708
2
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
3
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
4
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
5
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
6
Confections with Convictions
Kalamazoo, Kalamazoo County, Michigan·
5.0
(92) review
Kalamazoo's only shop making hand crafted truffles and other confections exclusively from Fair Trade, organic certified chocolate. Chocolatier Dale Anderson's original recipes contain fresh local fruits, honey, and maple syrup. Vegan and gluten free options are always available. Closed Sunday and Monday. Open Tuesday thru Saturday 10 a.m. until 6:00 p.m.
116 W Crosstown Pkwy, Kalamazoo, MI 49001-2732
7
River Trail
Lansing, Ingham County, Michigan·
4.5
(96) review
Lansing, MI 48912 ‎
8
Hudson Mills Metropark
Ann Arbor, Michigan·
4.5
(95) review
1,549-acre Park Has An 18-hole Golf Course.
8801 N Territorial Rd, Ann Arbor, MI 48130-9626
9
The Ark
Ann Arbor, Michigan·
4.5
(93) review
This music venue and nonprofit organization is dedicated to the presentation and encouragement of folk, roots and ethnic music through live performances by well-known and up-and-coming entertainers.
316 S Main St, Ann Arbor, MI 48104-2108
10
Kelsey Museum of Archaeology
Ann Arbor, Michigan·
4.5
(99) review
The Kelsey Museum houses a collection of nearly 100,000 objects from the civilizations of the Mediterranean.
University of Michigan 434 South State Street, Ann Arbor, MI 48109
11
Furstenberg Nature Area
Ann Arbor, Michigan·
4.5
(9) review
Fuller Road Opposite Huron High School, Ann Arbor, MI 48105
12
Decode Ann Arbor
Ann Arbor, Michigan·
5.0
(869) review
Discover adventures for teams large and small! Our award-winning escape rooms at Decode Ann Arbor take you around the globe and to destinations beyond your wildest imagination. Bring you friends and family and join in the fun!
3170 Packard St, Ann Arbor, MI 48108

CHECKLIST

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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Ann Arbor?
The distance is 241 miles
What's the travel time between Chicago and Ann Arbor?
The driving time can vary depending on traffic conditions, but it is typically 4h 38m mins in normal traffic
What are some of the best cities to visit between Chicago and Ann Arbor?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Ann Arbor?
There are plenty! Here are some stops you shouldn’t miss on your way to Ann Arbor
What’s the weather like in Ann Arbor?
The weather in Ann Arbor is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Ann Arbor in January
Weather in Ann Arbor in February
Weather in Ann Arbor in March
Weather in Ann Arbor in April
Weather in Ann Arbor in May
Weather in Ann Arbor in June
Weather in Ann Arbor in July
Weather in Ann Arbor in August
Weather in Ann Arbor in September
Weather in Ann Arbor in October
Weather in Ann Arbor in November
Weather in Ann Arbor in December
Interested in a detailed plan for your time in Ann Arbor?
Plan your dream Ann Arbor trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Ann Arbor
A 2-day itinerary in Ann Arbor
A 3-day itinerary in Ann Arbor
A 4-day itinerary in Ann Arbor
A 5-day itinerary in Ann Arbor
A 6-day itinerary in Ann Arbor
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