In Chicago, life revolves around the water. The city is lucky enough to be home to not one, but two stunning waterfronts.
The Chicago River winds through the heart of downtown, creating a skyscraper canyon lined with waterfront cafes. And Lake Michigan hugs the city’s eastern edge, with blue waters stretching to the horizon.
Top waterfront activities in Chicago
- Stroll the Chicago Riverwalk and pop into riverfront restaurants and bars
- Go kayaking or paddleboarding along the river
- Take an architecture boat cruise on the Chicago River or on Lake Michigan
- Dine on the sandy shores of Lake Michigan with waterfront restaurants
- Enjoy free public beaches with stunning skyline views
- Spend a day at Navy Pier, where you can hop on a scenic dinner cruise
This itinerary is designed to maximize time spent on and near the water. Spend a weekend exploring the best waterfront restaurants, attractions, and experiences in Chicago.
Important note: Keep in mind that many waterfront activities are seasonal, so always double check hours and availability before heading out.
Day 1: Explore the Chicago River
Morning: kayak through a skyscraper canyon
Start your day along the Chicago Riverwalk, the city’s popular pedestrian pathway filled with restaurants, bars, public art, and plenty of spots to take in the view.
Your first stop is Urban Kayaks. Start the day with a guided kayak tour of the Chicago River, where you’ll learn all about the city’s history while paddling past historic landmarks and soaring skyscrapers. It’s a uniquely Chicago experience you won’t soon forget.
Afternoon: lunch and an architecture cruise
Some of the hottest restaurants in town can be found along the riverbank. Sip a house-made wine at City Winery, kick back with a pint at The Northman Beer & Cider Garden, or enjoy colorful vibes and Mexican fare at TacoRio.
No visit to the Chicago River is complete without a classic Chicago architecture cruise. Choose from a variety of options that start and end right on the Riverwalk. The popular Chicago Architecture Center River Cruise covers the stories behind the city’s most iconic buildings.
After lunch, stop at the McCormick Bridgehouse & Chicago River Museum. Located inside one of the river bridgehouses, this unique museum showcases the history of the Chicago River and its famous moveable bridges. The top floor features panoramic views of the river and surrounding Riverwalk.
Evening: dinner and a show
Grab reservations for one of the many restaurants on the north side of the river, offering open-air dining rooms and patios with stunning water views.
Pizzeria Portofino has wood-fired pizzas and laidback vibes, River Roast serves refined American fare, and Smith & Wollensky is a long-time Chicago institution. For a special occasion, check out the upscale RPM Seafood.
Or for a unique experience, book a dinner cruise with City Cruises. The glass-enclosed vessel offers breathtaking views of the sparkling skyline.
After dinner, cross the bridge and grab a spot to watch Art on THE MART. This seasonal light show is the largest permanent digital art display in the world, featuring an ever-changing array of international artists.
Day 2: Experience Lake Michigan
Morning: paddleboard and explore the Lakefront Trail
Start your morning at the scenic North Avenue Beach, one of Chicago’s most popular beaches. At Chicago SUP, you can rent a paddleboard right on the sand or join a class for beginners — both offer an incredible vantage point of the downtown skyline. It’s the perfect way to kick off your day on the water.
For brunch, take the short walk up the shoreline to The Lakefront Restaurant. Located inside a historic building right on the water’s edge, this casual spot offers lakefront dining all year round.
If you’re staying near the South Side, you can recreate this same morning with paddleboard rentals at Chicago Water Sports Rentals at 31st Stret Harbor and the seasonal Pier 31 restaurant.
After you eat, spend some time walking the Lakefront Trail, an 18-mile pedestrian path that hugs the Lake Michigan shoreline. You can also rent a regular bike or e-bike from Divvy, the city’s bike share program, to cover more ground.
Afternoon: spend the day at Navy Pier
Spend the day at Navy Pier, a former naval ship dock transformed into a lakefront playground that’s one of the Midwest’s most visited attractions.
Take advantage of waterfront attractions, like the old-school carnival rides at Pier Park or the soaring Centennial Wheel, a massive climate-controlled Ferris wheel with spectacular views of the skyline. Grab a seat at Navy Pier Beer Garden to enjoy free live music and cold drinks.
Walk over to nearby Ohio Street Beach to stick your toes in the sand and enjoy the sights and sounds of Lake Michigan.
Evening: enjoy dinner on the water
Grab a reservation at Lirica, a modern spot on Navy Pier that blends Mexican, Spanish, Portuguese, and Caribbean flavors with sweeping water and city views. After dinner, grab a nightcap at nearby Offshore, the world’s largest rooftop bar.
Alternatively, Navy Pier is a perfect spot to hop on a dinner cruise on Lake Michigan. Choose from a variety of cruise options, including seasonal holiday and fireworks cruises, for a spectacular end to your weekend on the water.
