Looking for things to do in Chicago that the photo you’ve already seen a hundred times doesn’t cover? Try this: one free, roughly one-mile walk from a historic corner of State Street, down to the Chicago River, and west along the Riverwalk to a quiet stretch of floating gardens. Three stops, no tickets, and a better story than “we saw the Bean.”
The Bean is great, and you should see it. But the best moments of a trip usually happen at places you nearly walked past. This route is built around those places, and around giving yourself a reason to stop at each one.
The walk at a glance
- Route: State and Washington Streets → north on State to the river → west on the Riverwalk’s south bank to the River Theater (Clark to LaSalle) → the Jetty (Wells to Franklin).
- Distance and time: About a mile on foot. Plan on 1.5 to 2 hours if you actually linger, which is the point.
- Cost: Free. Everything here is public sidewalk or public Riverwalk; food, boat tours and drinks are optional extras.
- Good for: Solo wanderers, a pair of friends, or a group that can’t agree on a museum.
1. The corner of State and Washington: two buildings having a conversation
Stand at State and Washington and you’re looking at two of the Loop’s best-kept open secrets, hiding in plain sight above the shoppers. On the southwest corner is the Reliance Building, an 1895 tower by John Wellborn Root and Charles Atwood, wrapped in white terra cotta with so much glass it looks decades ahead of its time. It’s a city, state and national landmark.
Across the intersection, on the corner of the former Marshall Field’s store (now Macy’s), hangs the Great Clock, part of a clock tradition that began in 1897. Norman Rockwell put a man adjusting one of these clocks on a 1945 Saturday Evening Post cover. So you have a skyscraper and a clock from the same years, staring at each other across one intersection.
What SideQuest adds: a small hunt that makes you look at this block the way an architect would, at eye level and without stepping inside a single store. You’ll leave with a detail you would have missed and a reason it was worth stopping for.
2. The River Theater: where the street steps down to the water
Walk north on State to the river, take the signed stairs or ramp down, and head west along the Riverwalk. Between Clark and LaSalle you’ll reach the River Theater, which the landscape architects describe as “a sculptural staircase linking Upper Wacker and the Riverwalk,” with trees, seating and an accessible path running through it.
Sit down. From here the city rearranges itself: boats sliding past, bridges stacked one after another, towers looming over the far bank, and you below the traffic you just left. It’s one of the few places downtown where Chicago feels like it’s putting on a show for you specifically.
What SideQuest adds: the app hands you the director’s chair. The river, the boats and whatever happens to drift by become your material, and you walk away with something you made rather than another skyline photo that looks like everyone else’s.
3. The Jetty: floating gardens and a deliberate pause
Keep going west past Wells Street. Between Wells and Franklin, the Riverwalk turns quieter at the Jetty, “a series of piers and floating wetland gardens” where people fish and native plants grow right in the river.
This is the end of the walk, and it’s meant to feel like one. After a day of the city shouting at you, the Jetty is where you can let it carry on without you for a few minutes.
What SideQuest adds: a short, phone-down moment designed to leave you with one small Chicago memory, the kind that’s easier to carry home than the whole skyline. It’s a fitting last line for the day.
Practical tips before you go
- Getting down to the river: The Riverwalk sits below street level. There are signed stairs and ramps; if you need a step-free route, expect a short detour to the nearest ramp. Check the City of Chicago’s Riverwalk page for current hours and closures.
- Dress for the water: It’s often windier and cooler by the river than on State Street. Bring a layer.
- Be a good neighbor: Pause off to the side of sidewalks and stairs, and give anglers on the Jetty their space. Our guide to what not to do in Chicago has more.
- Add the classics if you like: Millennium Park and Cloud Gate are about a ten-minute walk east of the starting corner, so you can easily do both in a day.
See Chicago, then do something with it
Most city guides give you a list of places to look at. SideQuest gives you something to do once you get there. Chicago’s City Edition turns this walk, and more of the Loop and the river, into small quests: hunts, creative prompts and pauses that make a familiar landmark feel like your own discovery. The quests themselves stay in the app, so the surprises are still surprises when you arrive.
Play solo, or bring a friend and compare what you each found. Either way, you come home with more than a camera roll: a few little adventures, and the stories that go with them.
Download SideQuest, find Chicago, and give your next walk downtown a plot twist.