Things to Do at the Chicago Riverwalk: A Guide for Boaters
Last Updated on October 20, 2025 by Boatsetter Team
The Chicago Riverwalk stretches 1.25 miles along the south bank of the Chicago River, weaving together skyline views, waterfront dining, art installations, and boating access. For guests and hosts alike, it’s a dynamic gateway to the water and the city beyond. Here’s how to make the most of it.
A Quick Waterfront History
Once an industrial artery, the Chicago River has been transformed into an urban waterfront gem. Over the past two decades, large-scale revitalization has turned the Riverwalk into a public space with terraces, floating gardens, kayak launches, boat docks, and vibrant restaurants. (Wikipedia)
For boaters, this means docking or launching near one of the most bustling and photogenic waterways in the country — with city access, water access, and guests lined up for experiences on the water.
Top Boater-Friendly Stops Along the Riverwalk
City Winery at the Riverwalk
Address: 11 E Riverwalk South, Chicago, IL 60601
Overlooking the river, City Winery combines waterfront wines, light bites, and clear views of passing boats and downtown architecture. A great stop for guests before or after their charter.
Tiny Tapp
Address: 55 W Riverwalk, Chicago, IL 60601
For a casual drink, a live music vibe, and riverside seats, Tiny Tapp is the place to be. Guests often toast their boat day here—perfect for a post-charter social.
Pizzeria Portofino
Address: 317 N Clark St, Chicago, IL 60654
Hand-stretched pizza, a waterfront terrace, and skyline views make this one of the most guest-friendly dining stops near launch points.
The Jetty
Address: 260 W Wacker Dr, Chicago, IL 60606
Part of the Riverwalk’s “floating garden” section, The Jetty offers docks for small craft, informative signs about ecology, and a peaceful stretch away from the busier segments. (Wikipedia)
Art on the MART
Location: 222 W Merchandise Mart Plaza, Chicago, IL 60654
At night, the side of the Merchandise Mart transforms into a massive digital art canvas. If you dock or cruise past here in the evening, expect a spectacular backdrop. (Time Out Worldwide)
Chicago Architecture Center (CAC)
Address: 111 E Wacker Dr, Chicago, IL 60601
For hosts offering architecture-themed charters, the CAC provides excellent context. Guests can dock nearby and visit the museum, then board a boat tour of the river’s iconic buildings.
Boating Tips on the Riverwalk
- Use the designated boat access areas and check for dock availability before arrival.
- If launching a small craft or kayak, companies like Urban Kayaks operate from the Riverwalk and offer guided tours. (Urban Kayaks)
- Be aware of bridge schedules and currents, especially when navigating under downtown bridges.
- Remind guests the best photo moments are just past sunset when the skyline lights up the water.
- Boatsetter Insight: Docking or embarking near the Riverwalk adds immediate appeal to a listing—guests love the walk-off waterfront vantage and downtown proximity.
Why the Riverwalk Is Perfect for a Boat Day
From a host or guest perspective, the Riverwalk hits all the right chords:
- Launch near downtown and reach both the river and Lake Michigan without long transit time.
- Crystallize the “city-meets-water” experience—your charter goes from skyscrapers to open water.
- Guests can dine, stroll, and relax on shore—great for mixed itineraries (boat + land).
Final Thoughts
If you want to show off Chicago’s waterfront in the best light, launching from or cruising through the Chicago Riverwalk is hard to beat. Whether you’re listing a boat, hosting guests, or planning a private charter, the combination of views, amenities, and access makes this stretch of water one of the most valuable on the city’s map.
Explore available boats and charters in Chicago at Boatsetter.com and plan your next unforgettable experience.
