Unforgettable Riverwalk Gems Every First-Time Chicago Visitor Must See

Chicago’s Riverwalk is more than just a scenic stretch of waterfront—it’s a celebration of the city’s heart and soul. Lined with architectural marvels, buzzing restaurants, and charming public spaces, this 1.25-mile promenade along the Chicago River is a must for anyone visiting the Windy City for the first time. Whether you’re here for the skyline, the food, or just a good walk with a view, the Riverwalk delivers a picture-perfect experience.

Here’s your insider guide to the top Riverwalk attractions you absolutely can’t miss.

Unforgettable Riverwalk Gems

1. Marvel at the Chicago Architecture

As you stroll along the Riverwalk, you’ll find yourself constantly looking up—and for good reason. Chicago is a birthplace of modern architecture, and the Riverwalk offers one of the best vantage points to admire it. The soaring glass of the Trump Tower, the neo-Gothic Tribune Tower, and the sleek curves of the Aqua Tower are just a few of the structures that will catch your eye. Consider hopping on a Chicago Architecture Center boat tour (architecture.org) for an engaging, narrated ride through the city’s skyline.

2. Explore the McCormick Bridgehouse & Chicago River Museum

This underrated gem hides in plain sight beneath the DuSable Bridge. The McCormick Bridgehouse & Chicago River Museum is a celebration of Chicago’s history of engineering, showing off the massive gears that still help operate the bridge. As you ascend its spiral staircase, each level offers a new perspective of the river until you reach the top and are rewarded with a panoramic view. A perfect stop for curious minds and photo-lovers alike (bridgehousemuseum.org).

3. Chill Out at The Jetty

The Jetty section of the Riverwalk is where nature and recreation come together. It’s a floating garden made for relaxation, with walkways and seating areas that let you sit at water level and watch kayakers paddle by. If you’re feeling adventurous, rent a kayak from Urban Kayaks (urbankayaks.com) and glide under some of Chicago’s most iconic bridges. You’ll get a unique perspective on the city—and a little workout too.

4. Dine with a View at City Winery

Good food, fine wine, and river views—City Winery at the Riverwalk blends them all. This open-air venue is known for its relaxed vibe, live music, and a menu of wine-friendly dishes like gourmet flatbreads and cheese boards. Grab a table, order a glass of locally crafted wine, and enjoy the people-watching. Reservations are recommended during peak season (citywinery.com).

5. Snap the Perfect Selfie at the River Theater

One of the most visually striking spaces on the Riverwalk, the River Theater features a sweeping staircase that doubles as a hangout spot and an amphitheater. With the river flowing behind you and Michigan Avenue Bridge just ahead, it’s a favorite for both Instagram shots and relaxed breaks in the shade.

6. Take in Public Art and Sculptures

Chicago takes pride in its public art, and the Riverwalk acts like an open-air gallery. Look for installations like “The Radiance of Being” mural by Kate Lynn Lewis and the rotating Art on theMART projections on the Merchandise Mart. These vivid digital shows light up the riverfront at night and are best viewed from the Riverwalk’s central area (artonthemart.com).

7. Grab Sweet Treats at Tiny Tapp or Beat Kitchen on the Riverwalk

Looking for something quick, fun, and tasty? Stop by Tiny Tapp or Beat Kitchen, two beloved local eateries offering everything from sliders and fries to beer floats and craft cocktails. These walk-up counters are perfect for casual riverside dining without sacrificing flavor. Plus, you can enjoy your food just steps away from the river on their shaded patios.

8. Watch the Boats at the Marina Plaza

Marina Plaza is the Riverwalk’s ultimate spot for watching life go by. It’s home to leisurely boat traffic, tour groups, and water taxis. Sit back, sip on a cold drink, and enjoy the calming hum of the river. It’s also one of the most relaxing ways to soak up the sunshine and city buzz.

9. Visit the Vietnam Veterans Memorial Plaza

Tucked quietly into the Riverwalk, this solemn and beautiful plaza pays tribute to the soldiers who served during the Vietnam War. The design encourages reflection and remembrance, offering a calm break from the hustle of the downtown loop. It’s a meaningful moment of stillness along your walk—and one that adds emotional depth to your visit.

10. Catch a Sunset You’ll Never Forget

If there’s one thing you should plan your day around, it’s catching the sunset on the Riverwalk. As the city’s lights flicker on and the golden sun dips behind skyscrapers, Chicago’s magic truly reveals itself. Find a spot near the Franklin-Orleans Street Bridge and watch the water reflect the colors of the sky. It’s the perfect way to end your Riverwalk experience—and your day.

Ready to Walk the River?

The Chicago Riverwalk is open daily and free to access. Whether you have an hour or an entire afternoon, it promises something for everyone—from culture and cuisine to history and heart. So put on your walking shoes, charge your phone for all the photos you’ll take, and prepare to fall in love with Chicago one step at a time.

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