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By Huuk Team

Road trip from Indianapolis to Milwaukee

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ITINERARY

5h 23m272 miles5 stops
1
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.
2
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
3
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.
4
The Riverside Theater
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
5
Marcus Center
929 N Water St, Milwaukee, WI 53202-3122
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OVERVIEW

Get ready for an unforgettable adventure from the bustling streets of Indianapolis to the vibrant shores of Milwaukee! Embark on a journey that weaves through picturesque landscapes, charming towns, and historic landmarks. Along the way, you'll uncover hidden gems, immerse yourself in local cultures, and create memories that will last a lifetime.

Witness the transformation of the scenery as you leave the urban sprawl behind and enter a realm of rolling hills, tranquil lakes, and verdant forests. Discover quaint villages nestled amidst towering trees, where time seems to stand still and the pace of life slows down. Marvel at architectural wonders that tell tales of the past and inspire awe in the present.

As you approach the shores of Lake Michigan, a vibrant metropolis awaits your arrival. Explore its vibrant arts scene, indulge in culinary delights, and revel in the lively atmosphere. From towering skyscrapers to charming neighborhoods, Milwaukee offers a captivating blend of urban excitement and Midwestern charm. Let the spirit of adventure guide you as you embark on this incredible journey from Indianapolis to Milwaukee, where every mile holds a promise of discovery and delight.

1
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.
333 Michigan Ave, Chicago, IL 60601-3901
2
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
3
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
4
The Riverside Theater
Milwaukee, Wisconsin·
4.0
(95) review
116 W Wisconsin Ave, Milwaukee, WI 53203-2503
5
Marcus Center
Milwaukee, Wisconsin·
4.0
(94) review
929 N Water St, Milwaukee, WI 53202-3122

CHECKLIST

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Hand sanitizer and wet wipes
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Driver’s license and vehicle registration
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FAQ
Frequently Asked Questions
What's the driving distance between Indianapolis and Milwaukee?
The distance is 272 miles
What's the travel time between Indianapolis and Milwaukee?
The driving time can vary depending on traffic conditions, but it is typically 5h 23m mins in normal traffic
What are some of the best cities to visit between Indianapolis 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 Indianapolis?
We have a lot of great trip options for Indianapolis! See the links below for all the itineraries we created for you
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