The Best Sunsets in Chicago — and How to Watch Them From the Water
Chicago does sunsets differently. The combination of the flat Midwestern horizon, the lake, the river, and a skyline that was designed to be seen at every angle creates golden hours that are genuinely world-class. Here are the best spots in the city to watch the sun go down — and why the water beats all of them.
Montrose Beach
Montrose Beach on the North Side is one of Chicago's best-kept sunset secrets. Face west from the water's edge and you get the city skyline silhouetted against the orange sky, with Lake Michigan in the foreground. It's wide, relatively uncrowded compared to the more central beaches, and has a natural, unhurried energy. Bring a blanket and something to drink.
The 606 Trail
The 606 elevated trail on the Northwest Side offers a slightly elevated vantage point above the neighborhood rooftops. Watching the sunset from the trail as the city spreads out below you in all directions is a uniquely Chicago experience — urban, beautiful, and accessible from multiple neighborhoods.
Navy Pier
Navy Pier is touristy. But the sunset from the end of the pier — facing back toward the skyline with Lake Michigan at your back — is legitimately stunning. The architecture looks incredible backlit by golden hour, and if you time it right you can avoid most of the crowds. The Ferris wheel doesn't hurt either.
Ping Tom Memorial Park
One of the most underrated sunset spots in Chicago. Ping Tom sits on the South Branch of the Chicago River in Chinatown, directly facing the downtown skyline. As the sun sets behind the West Loop, the light hits the buildings and the river simultaneously, creating reflections and silhouettes that change minute by minute. It's quieter than the lakefront, more intimate, and the view of the skyline from this angle is one that most Chicagoans have never seen.
This is also where Neon Paddle launches its Golden Hour tours — which brings us to the best option on this list.
From the Water on a Neon Paddle Tour
Every single spot on this list has one thing in common — you're watching the sunset from the shore. The water version of all of them is better. Being on the river as the sun sets over Chicago means you're inside the scene rather than watching from the edge of it. The light hits you the same way it hits the buildings. The reflections surround you. The skyline is at eye level, not framed by a railing or a crowd.
Neon Paddle's Golden Hour tour is timed specifically for this. You launch from Ping Tom Park, head down the South Branch, and spend an hour on the water as the city transforms from afternoon gold to evening blue. The boards begin to glow as the light fades. The DJ is playing. The bridges frame the view above you.
It is, without exaggeration, the best way to watch a Chicago sunset. Not the most convenient, not the most famous — the best.
The sun sets different when you're on the river looking up at the city it's setting over.