Road Trip:
Chicago to Milwaukee, WI

Same delivery & return locations
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Embark on an exciting road trip from Chicago to Milwaukee, WI, a city known for its rich history, vibrant culture, and natural beauty. With Kyte's rental cars on demand, your adventure is more convenient and enjoyable than ever. Choose from our wide selection of vehicles and enjoy a hassle-free trip.

History of Milwaukee

Milwaukee has a fascinating history dating back to its early days as a Native American settlement. The city became an essential trading post in the 19th century and later evolved into a thriving industrial hub. Today, Milwaukee has preserved its historical sites, making it a perfect destination for history buffs and casual tourists alike.

Milwaukee harbor lighthouse

What Kind of Car You Should Rent to Get to Milwaukee

To ensure a comfortable and safe journey, select a vehicle that meets your needs and preferences. For a family trip or group adventure, consider renting an SUV or AWD for extra space and stability. For a more economical choice, opt for a sedan or economy car. During winter months, we recommend AWD vehicles.

How to Get to Milwaukee from Chicago

From downtown Chicago, head south on S Federal St towards W Van Buren St, then turn right onto W Ida B. Wells Dr. Continue onto IL-110 W, following signs for I-290 W, then merge onto I-90 W/I-94 W. Keep right to stay on I-94 W towards Milwaukee. As you reach I-294 N, merge and continue on I-94 W. After crossing into Wisconsin, continue onto I-43 N. Take exit 310C for I-794 E toward Lakefront, keep right at the fork, and then keep left to merge onto I-794 E.

The Route from O'Hare International Airport

Kyte services O'Hare International Airport (ORD) from a handover spot near ORD (not on airport property). We will meet you at our handover location at 3355 W Belmont Ave, Chicago, IL 60618. It's about a 25-minute ride-share ride away. Next, head west on W Belmont Ave and turn right onto N Kimball Ave. Turn left to merge onto I-90 W/I-94 W, then keep right to stay on I-94 W towards Milwaukee. Continue onto I-294 N and then I-94 W. After entering Wisconsin, continue onto I-43 N. Take exit 310C for I-794 E toward Lakefront, keep right at the fork, and then keep left to merge onto I-794 E.

The Route from Chicago Midway Airport

Kyte services Chicago Midway Airport (MDW) from a handover spot near MDW (not on airport property). We will meet you at our handover location at 1330 W Fulton Street, Chicago, IL 60607. It's about a 25-minute ride-share ride away. Then, head east on W Fulton St and turn left onto N Racine Ave. Turn right to stay on N Racine Ave and then right onto W Grand Ave. Turn left onto N May St, then right onto N Ogden Ave. Turn left to merge onto I-90 W/I-94 W and keep right to stay on I-94 W towards Milwaukee. Continue onto I-294 N and then I-94 W. After entering Wisconsin, continue onto I-43 N. Take exit 310C for I-794 E toward Lakefront, keep right at the fork, and then keep left to merge onto I-794 E.

Safety Tips for Driving From Chicago to Milwaukee

    • Stay alert and focused on the road

    • Follow traffic rules and speed limits

    • Use your seatbelt at all times

    • Keep a safe distance from other vehicles

    • Check the weather forecast and road conditions before your trip

    • Adjust your driving to suit weather conditions

Neon sign

Attractions in Milwaukee

Milwaukee boasts an array of attractions that cater to different interests, making it an ideal destination for a memorable road trip. Discover the city's vibrant arts and culture, fascinating history, and natural beauty by visiting popular attractions such as the Milwaukee Art Museum, Harley-Davidson Museum, Milwaukee County Zoo, or Historic Pabst Mansion.

Professional Sports

Milwaukee is home to several professional sports teams that provide an exciting experience for fans and visitors alike. The city's two major professional teams are the Milwaukee Brewers, who play in Major League Baseball (MLB), and the Milwaukee Bucks, members of the National Basketball Association (NBA). These teams have garnered dedicated fan bases and fostered a strong sense of community pride in the city.

The Milwaukee Brewers play their home games at the state-of-the-art American Family Field, formerly known as Miller Park. This impressive stadium, with its retractable roof, ensures that games can be enjoyed regardless of the weather. Attending a Brewers game is a quintessential Milwaukee experience that offers much more than just baseball. With delicious food, tailgating, and the famous Sausage Races, a day at American Family Field is fun for the whole family.

Similarly, the Milwaukee Bucks play at the Fiserv Forum, a modern, multi-purpose arena located in the heart of downtown Milwaukee. The Fiserv Forum is not only a sports venue but also a hub for entertainment, hosting concerts and other events throughout the year. Watching a Bucks game is an exhilarating experience, with passionate fans filling the arena and creating an electrifying atmosphere that is contagious. The arena's cutting-edge design and amenities also ensure a comfortable and enjoyable experience for all attendees.

Hiking and Biking

Discover the beauty of Milwaukee's picturesque parks and trails, which provide a perfect setting for hiking, biking, and immersing yourself in the great outdoors. With over 150 miles of biking and hiking trails, there is something for everyone, from the casual walker to the serious adventurer. Make sure to visit the Oak Leaf Trail, a 125-mile-long trail system that encircles Milwaukee County, offering a variety of terrains and landscapes to explore. From serene wooded areas and riverfront paths to urban streetscapes and scenic parks, this extensive network of trails caters to all abilities and interests.

Another must-see is the Lakefront Trail, where you can take a leisurely stroll or bike ride while enjoying the stunning views of Lake Michigan. This beautiful, paved pathway stretches over 6 miles and connects several major attractions, such as the Milwaukee Art Museum, Veterans Park, and the historic North Point Lighthouse. The trail is perfect for families, fitness enthusiasts, and sightseers alike, as it offers plenty of opportunities for picnicking, birdwatching, and photography.

For those looking for a more off-the-beaten-path experience, Milwaukee's many parks and nature preserves provide a host of hidden gems for hikers and bikers. Check out the beautiful Havenwoods State Forest, a 237-acre nature preserve that features a variety of ecosystems, including wetlands, grasslands, and woodlands, as well as an extensive trail system for hiking, birdwatching, and wildlife observation.

Shopping and Dining

Milwaukee boasts a diverse shopping and dining scene that caters to a wide range of tastes and preferences. The Historic Third Ward, a revitalized warehouse district, is a must-visit destination for shoppers. Here, you'll find a charming mix of boutique shops, art galleries, and specialty stores housed in beautifully restored buildings. As you stroll through the cobblestone streets, you'll discover unique items and local treasures that reflect the creativity and culture of Milwaukee.

When it comes to dining, the city offers a rich culinary landscape with an emphasis on farm-to-table restaurants. These establishments source their ingredients from local farmers and producers, ensuring a fresh and sustainable dining experience. From casual cafes to fine dining establishments, Milwaukee's diverse culinary offerings cater to various palates and budgets. Whether you're in the mood for traditional Wisconsin comfort food or innovative, globally inspired cuisine, you're sure to find a dining option that suits your taste.

Of course, a visit to Milwaukee would be incomplete without sampling some of the city's famous local beers. Known as the Brew City, Milwaukee has a long and storied brewing history, and today it is home to an array of breweries, brewpubs, and beer gardens. From iconic names like Miller Brewing Company to the thriving craft beer scene featuring smaller, innovative brewers, there is a beer to suit every preference. Take a guided brewery tour to learn more about the brewing process and the city's beer heritage, or simply relax at a beer garden and enjoy a pint while mingling with locals.

Annual Festivals in Milwaukee

Throughout the year, Milwaukee hosts several popular festivals that showcase the city's vibrant arts and culture scene. One of the most notable events is Summerfest, known as the world's largest music festival. Held annually along the scenic Lake Michigan shoreline, Summerfest attracts hundreds of thousands of visitors and features performances by both well-known and emerging artists from a wide range of genres. Spanning 11 days, this iconic festival offers an unforgettable experience filled with music, food, and entertainment, making it a must-visit event for music lovers.

Another significant event is the Milwaukee Film Festival, which celebrates the power of cinema by showcasing a diverse selection of local, national, and international films. This prestigious film festival, held annually over 15 days, offers a platform for filmmakers to share their stories and connect with audiences in an engaging and thought-provoking manner. The festival also features panel discussions, workshops, and special events that foster a sense of community and inspire a love for the art of filmmaking. By planning your trip around these events and others like them, you'll have the chance to experience Milwaukee's thriving arts and culture scene firsthand, creating lasting memories of your time in this vibrant city.


A road trip from Chicago to Milwaukee is a fantastic opportunity to explore the Midwest's rich history and lively culture. With Kyte's convenient rental car service, you can customize your journey and enjoy the freedom of the open road. Be sure to plan ahead and prioritize safety during your drive. Make the most of your trip by visiting Milwaukee's top attractions, indulging in its delicious cuisine, and participating in its unique festivals. Happy travels!

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