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By Huuk Team

Road trip from Chicago to Milwaukee

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iconMuseums
iconSights & Landmarks
iconClasses & Workshops
iconFood & Drink
iconConcerts & Shows
iconNature & Parks

ITINERARY

2h 0m94 miles9 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
The Riverside Theater
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
7
Marcus Center
929 N Water St, Milwaukee, WI 53202-3122
8
Miller Brewery Tour
4251 W State St, Milwaukee, WI 53208-3137
The Miller Brewery Tour offers an 80 minute indoor/outdoor guided walking tour of Miller Valley, home to over 155 years of brewing history. Experience everything from Fredrick Miller's arrival in Milwaukee to the high-speed production lines used today. Our tour begins with beer education and a journey back in time in our Historic Caves and Bavarian Style Miller Inn. Next we’re off to Brewing, Packaging & Distribution operations. Each tour ends as it begins… with our famous beers. Enjoy beer samples throughout the tour and after if 21+ with valid ID (soda and water available for those under 21). Commemorate your experience with a custom tour photo or one of the many great items found in our Girl In The Moon Brewery Shop. We look forward to seeing you for your Miller Time experience soon. CHEERS!
9
Lake Park
Milwaukee, WI
City park designed by Frederick Law Olmsted.
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OVERVIEW

Hop aboard an exciting adventure as we embark on a memorable journey from the bustling metropolis of Chicago to the charming city of Milwaukee. Along the way, we'll traverse a scenic landscape that unfolds like a vibrant tapestry, capturing the essence of the Midwest's natural beauty. Verdant fields dance in rhythm with the gentle breeze, while sparkling rivers meander through the countryside, creating a breathtaking panorama that will leave you mesmerized.

As we journey further along this captivating route, the urban sprawl gradually gives way to tranquil towns and quaint villages, each with its unique character and charm. Historic buildings whisper tales of the past, while modern marvels stand tall as testaments to progress. The air fills with the sweet scent of blooming flowers and the cheerful melodies of birdsong, creating a symphony that uplifts the spirits.

Our destination, Milwaukee, awaits us with open arms, promising an abundance of cultural and recreational treasures. From its renowned art museum to its vibrant culinary scene, Milwaukee offers a kaleidoscope of experiences that cater to every taste and preference. Immerse yourself in a world of discovery, where history intertwines with innovation, and where the spirit of the Midwest shines brightly.

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
The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
7
Marcus Center
Milwaukee, Wisconsin·
4.0
(94) review
929 N Water St, Milwaukee, WI 53202-3122
8
Miller Brewery Tour
Milwaukee, Wisconsin·
4.5
(939) review
The Miller Brewery Tour offers an 80 minute indoor/outdoor guided walking tour of Miller Valley, home to over 155 years of brewing history. Experience everything from Fredrick Miller's arrival in Milwaukee to the high-speed production lines used today. Our tour begins with beer education and a journey back in time in our Historic Caves and Bavarian Style Miller Inn. Next we’re off to Brewing, Packaging & Distribution operations. Each tour ends as it begins… with our famous beers. Enjoy beer samples throughout the tour and after if 21+ with valid ID (soda and water available for those under 21). Commemorate your experience with a custom tour photo or one of the many great items found in our Girl In The Moon Brewery Shop. We look forward to seeing you for your Miller Time experience soon. CHEERS!
4251 W State St, Milwaukee, WI 53208-3137
9
Lake Park
Milwaukee, Wisconsin·
4.5
(91) review
City park designed by Frederick Law Olmsted.
Milwaukee, WI

CHECKLIST

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GPS device or app
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Car charger and portable battery
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Water bottles and snacks
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Travel pillow and blanket
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Sunglasses and sunscreen
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First-aid kit
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Trash bags
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Hand sanitizer and wet wipes
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Driver’s license and vehicle registration
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Cash and cards
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Camera or smartphone
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FAQ
Frequently Asked Questions
What's the driving distance between Chicago and Milwaukee?
The distance is 94 miles
What's the travel time between Chicago and Milwaukee?
The driving time can vary depending on traffic conditions, but it is typically 2h 0m mins in normal traffic
What are some of the best cities to visit between Chicago and Milwaukee?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Milwaukee?
There are plenty! Here are some stops you shouldn’t miss on your way to Milwaukee
What’s the weather like in Milwaukee?
The weather in Milwaukee is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Milwaukee in January
Weather in Milwaukee in February
Weather in Milwaukee in March
Weather in Milwaukee in April
Weather in Milwaukee in May
Weather in Milwaukee in June
Weather in Milwaukee in July
Weather in Milwaukee in August
Weather in Milwaukee in September
Weather in Milwaukee in October
Weather in Milwaukee in November
Weather in Milwaukee in December
Interested in a detailed plan for your time in Milwaukee?
Plan your dream Milwaukee trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Milwaukee
A 2-day itinerary in Milwaukee
A 3-day itinerary in Milwaukee
A 4-day itinerary in Milwaukee
A 5-day itinerary in Milwaukee
A 6-day itinerary in Milwaukee
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