How to spend a weekend in the Windy City

How to spend a weekend in the Windy City

Clean and green, Chicago’s revamped Riverwalk has transformed the city’s urban environment.


Watching locals sipping wine, tucking into tacos, and walking their beloved pooches beside the Chicago River, it’s hard to believe this serpentine waterway was long shunned by residents of the Windy City. Yet thanks to a timely investment of 94.1 million euros (100 million USD), the river and its downtown environs are currently the hottest commodity in town.

The last stage of the Chicago Riverwalk, which stretches for around 1.5 kilometres from Lake Michigan to Wolf Point, was opened in October 2016. Extending across nine blocks, it is divided into distinct spaces, with features such as floating gardens, fishing piers, and fountains as well as an array of waterside wining, dining, and retail venues.

Hailed as the city’s “next recreational ­frontier” by Chicago Mayor Rahm Emanuel, the Riverwalk, together with ongoing river cleanup projects, has breathed new life into a part of the city that was once off limits thanks to pollution and problems with accessibility.

“The Riverwalk has refocused attention on the river, attracting a phenomenal number of people,” says Carol Ross Barney, lead design architect of the entire project. “By creating a new park in the centre of the city, it teaches us lessons in community, ecology, and sustainability.”

Kayak Chicago

What better way to explore the Chicago River than a kayak trip. Kayak Chicago have a rental centre just a short paddle from where the river flows into Lake Michigan. The company offers a variety of private and group tours, running from the spring right through until late autumn.

Chicago Architectural Foundation Cruises

An architectural hotbed, the city boasts buildings by such luminaries as Frank Lloyd Wright and Frank Gehry. Accessed from one side of the Riverwalk, cruises by the Chicago Architecture Foundation are often imitated but never equalled.

Bike and Roll

With several access ramps down to the Riverwalk, Chicago’s newest waterside feature makes the perfect cycling destination. Bike and Roll offers would-be cyclists a wide selection of well-maintained rental bikes, as well as quadcycles, segways, and guided bike tours.

Text and photos Daniel Allen