Chicago’s second shoreline, and the perfect way to extend an afternoon on the water.
As we stepped off the First Lady Architecture Cruise, we weren’t quite ready for the afternoon to end. Instead of heading back toward Michigan Avenue, we followed the gentle curve of the Chicago River, joining locals lingering over lunch, cyclists weaving past outdoor cafes, and visitors pausing every few steps to admire another remarkable skyline view.
The Chicago Riverwalk picks up exactly where the architecture cruise leaves off — a 1.25-mile pedestrian path tracing the south bank of the river from Lake Shore Drive to Lake Street — and it turned out to be one of the easiest, most pleasant hours of the entire trip.
From Industrial Channel to Star Attraction
It’s worth knowing the backstory, because it makes the walk more interesting. For most of its history, the Chicago River was a working industrial waterway — an artery for shipping, not strolling. The vision for a true riverside promenade dates back to Daniel Burnham’s 1909 Plan of Chicago, but it took until the early 2000s, with the reconstruction of Wacker Drive, for the project to truly take shape. The city accelerated the build-out through the 2010s, and the result is what you walk today: a series of distinct “rooms,” each with its own design and purpose, running in sequence along the water.
It’s a satisfying bit of urban transformation to take in while you’re standing in the middle of it — this glistening, cafe-lined walkway was once a place the city actively tried to keep people away from.
A Walk in Distinct Chapters
What makes the Riverwalk so easy to enjoy is that it doesn’t ask you to commit to one mood for the whole walk. Near Michigan Avenue, the Marina sections buzz with the comings and goings of tour boats and water taxis, with Marina Plaza offering benches and steps for simply sitting and watching the towers of Marina City rise across the water. Continue west and the energy softens at The Cove, a quieter pocket favored by kayakers, and at The Jetty, where open seating invites you to slow down and just watch the boats pass.
Further along, the path threads past the McCormick Bridgehouse and Chicago River Museum, worth a stop if you want the deeper history of the eighteen movable bridges that cross the river, and the Chicago Vietnam Veterans’ Memorial Plaza, a quiet, reflective space built directly into the riverfront. The variety is really the point — you can move from a lively wine garden to a contemplative memorial in the space of a few blocks.
Where to Pause
The dining and drinking options along the way are genuinely some of the best outdoor settings in the city. Elsewhere along the path, casual bars, beer gardens, and a rotating community marketplace of women- and minority-owned vendors keep the walk feeling current rather than purely scenic.
Why It’s the Perfect Pairing
Doing the Riverwalk directly after the First Lady architecture cruise made for one of the loveliest mornings of the entire trip. The cruise gives you the skyline from a distance and the stories behind it; the walk lets you close that distance, stand beneath the buildings you just learned about, and watch the river itself keep doing what it does best — flowing right through the center of the city’s identity.
Lisa’s Riverwalk Essentials
If you’re planning to spend an afternoon along the Riverwalk, here are a few items that made our walk more comfortable:
- Comfortable walking shoes
- Polarized sunglasseshttps
- Lightweight crossbody bag
- Portable charger
- Refillable water bottle
- Compact umbrella
- Lightweight sweater (if staying into the evening)
These are all items that would be equally useful on the First Lady Architectural Cruise.
Lisa’s Take
★★★★★
Would I recommend it?
Absolutely.
Best For
First-time visitors, architecture enthusiasts, photographers, couples, and families with older children.
Allow
About 2½ hours, including boarding and time to explore the Riverwalk afterward.
For the rest of where we stayed, ate, and explored on this trip, look for the complete Chicago guide coming soon to The Insider’s Guide. In the meantime, stay tuned for the next stop in my Chicago blog series!
