In the fourth installment of our epic road trip series, we continue our journey through the American Midwest – traveling from the music-rich city of Detroit to the bustling metropolis of Chicago. Along the way, you’ll encounter vast lakes, charming small towns, historic highlights, and that unmistakable road trip vibe. This leg is perfect for anyone who loves a mix of culture, nature, and classic American diner charm.

Leg 4 of 11: Overview

The drive from Detroit to Chicago covers roughly 460 kilometers (285 miles). You could tackle it in just over five hours non-stop, but following the scenic shores of Lake Michigan opens up a world of discoveries – from quaint harbor towns and sandy beaches to Indiana Dunes National Park and, finally, Chicago’s iconic skyline.

Let’s Hit the Road: Saying Goodbye to Detroit

After soaking up Detroit’s museums, vibrant street art, and legendary sports stadiums, it’s time to head west.

Stop 1: Kalamazoo – Small-Town Charm Meets Vineyard Vibes

This lively university town in western Michigan has an infectious energy. Amid historic architecture and colorful murals, you’ll find students and artists bringing the streets to life. Western Michigan University shapes the city’s youthful character, alongside an array of cozy galleries, vintage shops, and buzzing live music bars downtown. The region is also famous for its craft beer scene, with Bell’s Brewery standing out as a local favorite.

Stop 2: St. Joseph on Lake Michigan

Nestled right on Lake Michigan, St. Joseph offers the perfect blend of relaxation and small-town charm. Spend time at Silver Beach’s wide sandy shore, snap photos of the picturesque lighthouse, and wander the quaint downtown area. The real magic happens at sunset – watching the sky and water glow is a genuine vacation moment.

Stop 3: Michigan City, Indiana

Located on the southern shore of Lake Michigan, Michigan City is a great place to unwind. The Washington Park Beach with its pier and lighthouse becomes especially captivating at sunset. If you’re in the mood for shopping or some cultural exploration, the Lighthouse Place Premium Outlets have plenty to offer.

Stop 4: Indiana Dunes National Park

Just before reaching Chicago, you’ll find this stunning national park – a true nature lover’s paradise. With rolling sand dunes, dense forests, pristine beaches, and scenic overlooks, it’s a refreshing stop. On a clear day from West Beach, you can even catch your first glimpse of Chicago’s impressive skyline shimmering in the distance.

Stop 5: Chicago, Illinois – The Windy City

At last, you arrive in Chicago, a vibrant city sitting proudly on Lake Michigan with one of the most breathtaking skylines in the US.

Chicago Must-Sees:

• Millennium Park & the iconic “Bean” sculpture
• Chicago Riverwalk
• Museums Campus & Lakefront Trail

Reading tip: Compact Chicago: 48 Hours of Eats, Arts & Iconic Cityscapes

Tips for the Drive

• Traffic: As you approach Chicago, traffic tightens – try to avoid arriving during rush hour.
• Scenic Breaks: If you have time, plan a longer stop in St. Joseph or at Indiana Dunes Beach to fully enjoy the views.

Our conclusion: This stretch is a classic road trip experience – laid-back, and packed with off-the-beaten-path discoveries beyond the Interstate. In our next chapter, we’ll head further west, crossing Wisconsin and Minnesota all the way to the Badlands National Park.

St. Joseph or Michigan City – which would you choose for a Great Lakes stopover?
Let us know in the comments & tag your favorite road trip buddies!

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