Good evening, city walkers. The Chicago Riverwalk gives you a view of downtown from below the bridges, where the buildings appear much taller than they do from the street. Begin while there is still daylight, when it is easy to distinguish older stone buildings from the glass towers beside them.

Then stay for the point in the evening when the sky still has colour and the lights have come on. You can enjoy both parts of the walk without needing to cover the entire riverfront.

Start at Michigan Avenue

Begin near the Michigan Avenue bridge. Look toward the pale Wrigley Building and its clock tower before you go down to the path. At street level, the view includes traffic and people on their way across. From the Riverwalk, the river gives the buildings more space. Check where you will come back up, particularly if anyone in the group needs a ramp instead of stairs.

The Riverwalk is free to enter. Walk west on the south bank and pause under a bridge to see how its underside frames the next stretch of water. Leave room for people coming the other way, since the path narrows at some points. Wind feels stronger beside the river than it does on a sheltered street, so carry a layer even if you expect to be outdoors for only an hour. If you want a shorter walk, use State Street as a turning point. The ramp there is also useful when you want to change levels without taking the steps.

Look Across the Water at the Buildings

As you walk, compare the tops of buildings with what you can see at river level. An older building might have small windows and decorative stonework near the street, while a glass tower beside it reflects the sky in broad panes. Looking across the water makes those differences easier to see than standing at the foot of either building.

Give each bend its own look. Boats and low bridges can draw your attention close to the surface, while a gap between buildings opens a view farther into the city. For evening photographs, stand where you can keep your hands steady and leave room on the path. The lights in the water often hold their colour even after the buildings themselves have fallen into shadow.

Take the Architecture Cruise

The Chicago Architecture Center’s river cruise aboard First Lady takes about ninety minutes, with tickets starting at US$57 per person. Check the boarding instructions and the date you want, since the cruise runs on a seasonal schedule. Give yourself enough time to reach the dock from street level. Ask about the ramp or drop-off arrangements if stairs are difficult.

A guide can help you see details that might otherwise go unnoticed, particularly where the boat turns and shows several sides of a building in quick succession. If you plan to stay on foot, choose one stretch of the Riverwalk and spend longer on it. An evening walk with a meal afterwards gives you the freedom to wait for the sky and the water to change at their own pace.

Stay Close to the Bridges

River Hotel has rooms from about US$73 a night. Its Wacker Drive location makes it easy to reach the river and the streets around Michigan Avenue. Check the room type and the full price before booking, especially if you want a river view. The location works well when you expect to spend most of your time out and want a short walk back afterwards.

LondonHouse Chicago has rooms starting at about US$115 a night. Its position beside the Michigan Avenue bridge suits travellers who want to begin and end the day at the same river bend. Compare room size, outlook and final charges with the other option for the same dates. A bridge-side base is particularly useful if you plan to return after a cruise or want to see the river again before breakfast.

At the end of the walk, look back from street level. The river that took up most of your view below the bridges will now appear between the buildings in brief, bright glimpses.