Things to Do at the Chicago Riverwalk: A Guide for Boaters

Written by Boatsetter Team
September 23, 2024

Last Updated on September 23, 2024 by Boatsetter Team

Stretching 1.25 miles along the Chicago River, the Riverwalk seamlessly blends stunning architectural views, vibrant dining options, and diverse recreational activities into one dynamic waterfront experience. Dive into our quick guide and discover the top things to do for boaters when you visit the Chicago Riverwalk.

Explore boat rentals in Chicago

A Brief Riverwalk History

The Chicago Riverwalk is part of a larger effort to revitalize the Chicago River. Given the city’s industrial heritage, the water was contaminated and toxic for many years. Work to improve the river’s ecological health, support local wildlife, and promote sustainability has drastically transformed the river and turned the Riverwalk into a hub that captures the essence of Chicago’s unique culture, cuisine, and history.

Things to do along the Chicago Riverwalk

Chicago Riverwalk Things to Do

City Winery at the Riverwalk

11 E Riverwalk South, Chicago, IL 60601

City views, refreshing wine, and delicious food await at the City Winery along the Riverwalk. Guests love enjoying their drinks right on the water, where they can watch boats and kayaks go by and take in the iconic Chicago skyline.

 

Tiny Tapp

tiny tapp

55 W Riverwalk, Chicago, IL 60601

If you want live music, crafted cocktails, and quality coffee all in one place, then Tiny Tapp is a must. Cool off with a frozen cocktail and Chicago-style hot dog in the summer, or cozy up with a hot latte and warm chocolate chip cookie in the winter months.

 

Pizzeria Portofino

317 N Clark St, Chicago, IL 60654

Pizzeria Portofino is a chic waterfront restaurant in Chicago, great for romantic dates and special occasions. Enjoy hand-stretched pizzas, flavorful wines, and signature dishes. Visitors highly recommend the Black Truffle & Three Cheese Pizza and the Lemon Tiramisu for dessert.

Explore more Chicago Restaurant’s on the water

The Jetty

The Jetty Chicago

260 W Wacker Dr, Chicago, IL 60606

At the corner of W Wacker Drive and N Orleans St is the Riverwalk Jetty. The Jetty is an integral part of the larger Riverwalk project. Floating gardens and wetlands are designed to improve water quality and provide a habitat for local wildlife, ultimately supporting biodiversity in the Chicago River. Educational exhibits make this a great spot to bring children.

 

Art on the Mart

222 W Merchandise Mart Plaza, Chicago, IL 60654

Visit one of the largest digital art installations in the world at Art on the Mart. The Mart itself is an architectural landmark and works in collaboration with Chicago’s Department of Cultural Affairs and Special Events to transform the face of the building into a canvas for innovative public art. Be sure to check the Art on the Mart website for details on featured installations during your trip.

 

Chicago Architecture Center

111 E Wacker Dr, Chicago, IL 60601

The Chicago Architecture Center (CAC) is a must-do activity for boaters in Chicago. Renowned for its architecture boat tours, the CAC offers guided cruises that provide stunning views of the city’s famous skyscrapers with insightful commentary on the buildings’ design, history, and impact. You can also explore exhibits inside the center, including interactive displays, scale models, and a hands-on design studio.

 

Navy Pier

600 E Grand Ave, Chicago, IL 60611

Your visit to the Chicago Riverwalk won’t be complete without a stop at the Navy Pier. This iconic attraction offers a variety of activities, making it a perfect destination for families. The Centennial Wheel has some of the best panoramic city views, the Chicago Children’s Museum is a great place for little ones to run around, and a diverse range of waterfront restaurants like Offshore Rooftop & Bar provide the perfect setting for relaxation. Be sure to check out the Navy Pier website for seasonal events like the Chicago Air and Water Show and the Butterfly House.

Learn more about Chicago marinas

Boating Tips

As you navigate Chicago’s waterways with your Boatsetter boat rental you’ll want to make sure to check for available docking slips and obtain necessary permits in advance. For up-to-date information on permits, fees, and docking availability, visit the Chicago Harbors website.

For the best weather conditions, we recommend visiting in the summer months. If you’re looking to beat the crowds and save during the less busy times of year, then plan your Chicago trip in the spring or fall.

Boating on the Chicago River

Whether you’re looking for entertainment, education, or culture, the 1.25 mile stretch of the Chicago Riverwalk offers something for everyone. Plus, between the rest of the Chicago River and easy access to Lake Michigan, the Riverwalk only scrapes the surface of what you can do by boat in Chicago.

About us

Boatsetter is the leading online marketplace for boat rentals and on-water experiences. Download the Boatsetter app (App Store | Google Play) and follow us on Instagram.


Browse by experience


Explore articles