Perfect Family Road Trip Itinerary
Planning a Wisconsin road trip from Milwaukee to Chicago? You’re in for a treat. This route offers a mix of scenic views, exciting stops, and fun activities. Here’s a detailed itinerary to make your journey memorable.
Morning Departure from Milwaukee
Start your adventure with a hearty breakfast at Blue’s Egg. Known for its delicious menu and friendly service, it’s a great way to fuel up for the trip ahead. From there, head south on I-94, which will take you straight to Chicago.
Stop 1: Kenosha
After about 40 minutes, you’ll reach Kenosha. Visit the Kenosha Public Museum for a quick dose of culture. With free admission and fascinating exhibits, it’s a hit for both kids and adults.
Stop 2: Pleasant Prairie Premium Outlets
Just a short drive from Kenosha, this outlet mall is perfect for a shopping break. You’ll find great deals on popular brands. Let the kids stretch their legs while you explore the stores.
Lunchtime in Waukegan
Continue your journey to Waukegan and stop for lunch at Anastasia’s Restaurant & Sports Lounge. Known for its family-friendly atmosphere and diverse menu, it’s an ideal spot to relax and recharge.

Stop 3: Six Flags Great America
For some thrilling fun, spend a few hours at Six Flags Great America in Gurnee. This amusement park has rides and attractions for all ages. It’s a highlight of any road trip itinerary.
My Perspective: Family Bonding on the Road
A Wisconsin road trip is more than just traveling from one place to another. They offer a fantastic opportunity for family bonding. My husband and I love taking our two kids on these adventures.
We create lasting memories, sing along to our favorite songs, and discover new places together. One of our favorite resources is the Wisconsin road trips book, which has inspired many of our journeys.
Stop 4: Naval Station Great Lakes
History buffs will enjoy a quick visit to the Naval Station Great Lakes. It’s the Navy’s largest training station, offering insightful tours and exhibits. The kids will love seeing the ships and learning about naval history.
Arrival in Chicago
Arrive in Chicago in the late afternoon. Check into your hotel and unwind before heading out for dinner. Consider staying at the historic Palmer House Hilton, located in the heart of downtown. It offers luxurious accommodations and is close to major attractions.
Evening Fun in Chicago
End your day with a visit to Navy Pier. Enjoy the stunning city skyline, ride the Ferris wheel, and indulge in some tasty treats. It’s a wonderful way to cap off your road trip.
Final Thoughts: Hit the Road
A road trip from Milwaukee to Chicago is perfect for families seeking adventure and quality time together. Follow this itinerary for a mix of culture, fun, and relaxation. Grab your Wisconsin road trips book, pack some snacks, and hit the road for an unforgettable journey.

I really like to write about travel. Once in a while I get to enjoy it as well, but sharing all of the great places that you can visit around Lake Michigan is just as exciting for me. I have 2 pets, and now you know that.



