Cool Places to Stop Between Milwaukee and Chicago
Stormy Sky in Pewaukee Wisconsin

Milwaukee, Wisconsin and Chicago, Illinois are conveniently located about two hours apart. They are the perfect distance for a short Midwest road trip! There are lots of cool places to stop between Milwaukee and Chicago. This guide includes state parks and natural sites, as well as great restaurants, fun photo-ops, and more!

Cool Parks Between Milwaukee & Chicago

View of Lake Michigan from the Illinois Beach Resort in Zion Illinois

Illinois Beach State Park is a beautiful lakeside gem just south of the Wisconsin-Illinois border. It is one of my favorite places to stop between Milwaukee and Chicago! This park is known for its beautiful beaches and sand dunes. It is a great place to stop for a beach day or to go for a hike. The best place to hike in the park is along the nature trails along its southern end. If you want to make an overnight pit stop on your road trip from Milwaukee to Chicago, the Illinois Beach Resort is located within the park! This Best Western Premier site is the only lakeside hotel in Illinois.

Spring at Richard Bong State Recreation Area in Kenosha County Wisconsin

Richard Bong State Recreation Area is southeastern Wisconsin’s largest managed prairie and a great place to hike! Located in western Kenosha County, it offers a nice break from the busy city and is easily accessible from I-94. While the park is open year-round, it is especially beautiful in the spring. You can read my hiking guide for the park to help plan your visit. Daily admission costs $8 per car or is free the purchase of an annual vehicle admission sticker.

Best Places to See Lake Michigan

ReefPoint Marina and Lake Michigan in Racine Wisconsin

Reefpoint Marina in Racine offers beautiful views of Lake Michigan. Less than an hour south of Milwaukee, Racine is a great place to enjoy time by the water while escaping the crowds. Take a walk along the causeway for the perfect overlook of the lake and the city skyline. This is one of the best places for a photo-op in Racine! Fuel-up while you’re there at the harborside Reefpoint Brew House restaurant.

Boat Approaching the Harbor in Kenosha Wisconsin

The promenade in Kenosha’s HarborPark neighborhood is a beautiful place to look out over Lake Michigan and watch boats drive in and out of the harbor. It is close to many great restaurants and the Kenosha Public Museum, making it a convenient place to stop between Milwaukee and Chicago. I first visited with my mom on a day trip to Kenosha last year and was very impressed. I plan to visit again this summer!

Cool Restaurants Between Milwaukee & Chicago

Rainforest Cafe Sign in Gurnee Illinois

Take a detour to the jungle (no bug spray needed) on your road trip with a visit to the Rainforest Cafe. This restaurant and store is an especially fun place for kids, but is enjoyable for people of all ages. Their eclectic menu makes this a great place to stop when you want to eat something different than usual. As the restaurant is located within the Gurnee Mills mall, you can also make this a longer stop and walk around!

Exterior of the Mad Rooster Cafe in West Milwaukee Wisconsin

Mad Rooster Cafe offers country-style dining just minutes from Milwaukee. It is a great place to stop and enjoy breakfast or lunch before driving to Chicago. I have visited many times with family and friends and find something new on the menu each time. I especially love their cinnamon French toast!

Fun Photo-Ops Between Milwaukee & Chicago

Murals in Racine, WI

In Front of a Mural in Uptown Racine Wisconsin

Racine, Wisconsin is a beautiful city with a lot of history. In addition to historic buildings and scenic lake views, there are a bunch of fun murals to stop at for a quick pic on your drive from Milwaukee to Chicago! Click here for my complete list of the most Instagrammable spots in Racine.

"Welcome to Wisconsin" Sign (10519 120th Avenue, Pleasant Prairie, WI)

Welcome to Wisconsin Sign in Pleasant Prairie

The Wisconsin Welcome Center in Pleasant Prairie, Wisconsin is a great place to get travel information as you head north along I-94 into Wisconsin. You can also pose for a picture in front of the “Welcome to Wisconsin” sign on-site.

Cool Places to Stop Between Milwaukee and Chicago

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