There’s just something magical about hugging Lake Michigan’s shoreline with the windows down, breeze in your hair, and that unbeatable Midwestern charm surrounding you. The Lake Michigan Circle Tour is iconic—and Chicago? It’s the glittering crown jewel of the whole drive. Whether you’re a local looking for new gems or a road-tripper chasing lakeside vibes, we’ve got the ultimate list of stops you need to hit when driving through the Windy City.

🏖️ 1. North Avenue Beach – Sand, Skyline, and Sunsets

This is Chicago’s beach with an attitude. You’ve got volleyball courts, rentals, beach bars, and that postcard-perfect skyline just chilling in the background. If you're visiting in the summer, expect energy levels to be off the charts—music playing, tanners tanning, and jet skis flying by.

Don’t Miss: Castaways Bar & Grill—grab a frozen drink and some tacos while watching the lake glisten like a sapphire.

🎨 2. Navy Pier – More Than Just a Ferris Wheel

This historic pier is a classic Chicago must-see. It’s not just for tourists—locals love it too. From boat rides and waterfront dining to live performances and fireworks on summer nights, Navy Pier is a sensory overload in the best way.

✅ Hot Picks:

• Centennial Wheel for epic 360° views

• Offshore Rooftop (largest rooftop bar in the country!)

• Chicago Shakespeare Theater, if you’re feeling artsy

🏞️ 3. Promontory Point – Chill Zone With a View

If you’re looking to escape the crowds and snap some unreal skyline pics, head south to Hyde Park’s best-kept secret. Promontory Point is part of Burnham Park, and it’s like stepping into another world. Think grassy knolls, old stone architecture, and peaceful shoreline strolls.

🌟 Vibes: Romantic picnic? Yes. Reading spot? Yes. Skipping rocks and watching boats go by? Also yes.

🚴 4. The Lakefront Trail – Two Wheels, One Epic Ride

The 18-mile Lakefront Trail is a bucket-list experience. Rent a bike (or e-bike) and cruise from Edgewater down to South Shore, with everything from beaches to parks along the way. Locals love it for jogging, skating, and just soaking in lakefront life.

⚠️ Heads Up: Try to go early morning or late afternoon to beat the tourist rush and catch the best lighting for your selfies.

🛶 5. Kayak Chicago – Paddle Past Skyscrapers

Yes, you read that right—you can kayak through downtown Chicago. Kayak Chicago offers guided tours that launch from the river and head toward the lakefront. It’s equal parts workout and “whoa, is this real life?”

💧 Pro Tip: Book the sunset architecture tour—it’s ridiculously beautiful and the guides are full of fun facts that’ll blow your mind.

🎉 Bonus Stop: Museum Campus

Okay, it’s technically not just one stop, but the Museum Campus brings together the Shedd Aquarium, Field Museum, and Adler Planetarium—all with panoramic lake views. Park it here and let curiosity take the wheel.

🚗 Ready to Roll?

The Lake Michigan Circle Tour through Chicago is a seriously unforgettable ride—but to do it right, you need a set of wheels that’s ready for the adventure. Book your car with Chicago Adventure Rentals and make the journey smooth, stylish, and stress-free.

👉Secure your rental now or call us at +1 872-296-8008. Let’s hit the road and soak up that lakeside magic, Chicago-style.