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Road trip from Waukegan to Waukesha
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Nature & Parks
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ITINERARY
1h 24m64 miles11 stops
1
Rhapsody Theater
A newly reopened theater is Chicago. The Rhapsody Theater is a beautiful, intimate, elegant venue with Valet Parking, Restaurant, and 3 bars. World Class Magic, Chamber Music, Comedy, Jazz and more.
2
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.
3
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
4
Klassic Limousine, Inc
Thank you for choosing Klassic Limousine, Inc-your true North for the Wisconsin luxury transportation market. We are proud to be your first choice in Milwaukee, and we take your vote of confidence in us very seriously, and welcome you to VIP treatment on a larger scale. Based in Milwaukee, Klassic Limousine, Inc is all about luxury and elegance. As the undisputed leader in luxury we know how to deliver the VIP treatment the passenger expects. Founded with a desire to bring the best in luxury and modern class to our discerning clients, we are now the finest Milwaukee black car service. This is based on our commitment to being not only the best in urban transportation, but the best overall in terms of vehicle luxury and professionalism. With Klassic Limousine, Inc you travel your way. All of the above combined make us a superior Milwaukee limousine service. Therefore, when you choose Klassic Limousine, Inc you can rest assured that an unforgettable experience awaits you.
5
South Shore Park
Beautiful park on the lake shore. Great view of city in the distance. Nice place to play in the water or have a picnic.
6
Marquette University
7
The Riverside Theater
8
Marcus Center
9
Miller Brewery Tour
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!
10
Shank Hall
11
Lake Park
City park designed by Frederick Law Olmsted.
Customize this Trip
OVERVIEW
Hop aboard and get ready to explore the vibrant landscapes and hidden gems that lie between the bustling city of Waukegan and the charming town of Waukesha. Embark on a journey that weaves through rolling hills, meandering rivers and picturesque countryside, where every turn promises a new adventure.
Discover the rich heritage and cultural tapestry that unfolds along the way. Immerse yourself in the captivating stories and traditions that have shaped this region, from the vibrant arts scene to the thriving culinary landscape. Meet the friendly locals who are eager to share their unique perspectives and create lasting memories.
Indulge in the natural beauty that surrounds you. Take a leisurely stroll through lush parks, marvel at breathtaking vistas from scenic lookouts, and uncover the secrets of hidden waterfalls. Whether you seek tranquility in nature or the excitement of urban exploration, this journey offers an unforgettable blend of experiences that will ignite your senses and leave you longing for more.
1
Start:Rhapsody Theater
Chicago, Illinois·
4.5
(9) review
A newly reopened theater is Chicago. The Rhapsody Theater is a beautiful, intimate, elegant venue with Valet Parking, Restaurant, and 3 bars. World Class Magic, Chamber Music, Comedy, Jazz and more.
2
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.
3
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
4
Start:Klassic Limousine, Inc
Milwaukee, Wisconsin·
4.5
(9) review
Thank you for choosing Klassic Limousine, Inc-your true North for the Wisconsin luxury transportation market. We are proud to be your first choice in Milwaukee, and we take your vote of confidence in us very seriously, and welcome you to VIP treatment on a larger scale. Based in Milwaukee, Klassic Limousine, Inc is all about luxury and elegance. As the undisputed leader in luxury we know how to deliver the VIP treatment the passenger expects. Founded with a desire to bring the best in luxury and modern class to our discerning clients, we are now the finest Milwaukee black car service. This is based on our commitment to being not only the best in urban transportation, but the best overall in terms of vehicle luxury and professionalism. With Klassic Limousine, Inc you travel your way. All of the above combined make us a superior Milwaukee limousine service. Therefore, when you choose Klassic Limousine, Inc you can rest assured that an unforgettable experience awaits you.
5
Start:South Shore Park
Milwaukee, Wisconsin·
5.0
(9) review
Beautiful park on the lake shore. Great view of city in the distance. Nice place to play in the water or have a picnic.
6
Start:Marquette University
Milwaukee, Wisconsin·
4.5
(89) review
Milwaukee, WI 53201-1881
7
Start:The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
8
Start:Marcus Center
Milwaukee, Wisconsin·
4.0
(94) review
929 N Water St, Milwaukee, WI 53202-3122
9
Start: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!
10
Start:Shank Hall
Milwaukee, Wisconsin·
4.0
(9) review
1434 N Farwell Ave, Milwaukee, WI 53202-2904
11
Start:Lake Park
Milwaukee, Wisconsin·
4.5
(91) review
City park designed by Frederick Law Olmsted.
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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Frequently Asked Questions
What's the driving distance between Waukegan and Waukesha?
The distance is 64 miles
What's the travel time between Waukegan and Waukesha?
The driving time can vary depending on traffic conditions, but it is typically 1h 24m mins in normal traffic
What are some of the best cities to visit between Waukegan and Waukesha?
Some popular stops include
Are there any cool sights or attractions I shouldn't miss on my drive to Waukesha?
There are plenty! Here are some stops you shouldn’t miss on your way to Waukesha
What’s the weather like in Waukesha?
The weather in Waukesha is generally mild year-round, with warm, dry summers and cool, wet winters. See the links below for more information
Weather in Waukesha in January
Weather in Waukesha in February
Weather in Waukesha in March
Weather in Waukesha in April
Weather in Waukesha in May
Weather in Waukesha in June
Weather in Waukesha in July
Weather in Waukesha in August
Weather in Waukesha in September
Weather in Waukesha in October
Weather in Waukesha in November
Weather in Waukesha in December
Interested in a detailed plan for your time in Waukesha?
Plan your dream Waukesha trip with our daily itineraries featuring must-see attractions! See them here!
A 1-day itinerary in Waukesha
A 2-day itinerary in Waukesha
A 3-day itinerary in Waukesha
A 4-day itinerary in Waukesha
A 5-day itinerary in Waukesha
A 6-day itinerary in Waukesha
Where else can I travel to if I'm starting my trip in Waukegan?
We have a lot of great trip options for Waukegan! See the links below for all the itineraries we created for you
