Ten things to do in Chicago for free

21.07.2023 - 07:55 / roughguides.com / Frank Sinatra

To paraphrase Frank Sinatra’s crooned take on the city, Chicago can be your kind of town — even if you’re skint. Here's my top ten tips to enjoy the city for nothing.

The Museum of Contemporary Photography at Columbia College does what it says on the tin. There’s more free photography at the City Gallery in the Historic Water Tower, a survivor of the Great Chicago Fire. «No Ketchup: Photographs of Chicago Hot Dog Stands» was one exhibition that doubled as a lesson in important local culinary folklore – don’t try asking for tomato sauce on your dogs in these parts. Close to Millennium Park, the Chicago Cultural Center draws visitors for its wide-ranging programme – including the Dame Myra Hess Memorial concert series – and beautiful stained-glass domes.

A number of first-come, first-served tours are available around the city on Wednesdays. Try the Charnley-Persky House, the Clarke House Museum, or the Glessner House Museum (whose architecture was an inspiration to Frank Lloyd Wright).

Chicago River © Mark Baldwin/Shutterstock

All the beaches along the lake are great but this is the best of the bunch. Less crowded than Oak Street, it offers superb city views as you dip your toes in Lake Michigan. It’s also one of the best beaches for open swimming. The lakefront itself runs 28 miles – walk it, jog it or bike it.

Jane Byrne, the city’s only female mayor to date, once said that “Chicago’s neighborhoods have always been the city’s greatest strength". Try the Old Town Triangle in the Lincoln Park neighbourhood, with buildings that pre-date the Great Chicago Fire of 1871. Head to Oak Park, where Frank Lloyd Wright built 25 homes and developed his famed Prairie style. He lived and worked at 951 Chicago Avenue. You have to pay for a tour, but nobody’s going to stop you checking out the exterior.

For more Wright homage-paying, go to The Rookery. The architect oversaw an early-20th-century renovation of the beautiful building, and it’s been associated with him ever since, even if the original architects were Daniel Burnham and John Root. Completed in 1888, it was the tallest building in the world and boasted a world-first indoor shopping arcade. Tours of the building are available for $5–$10, or you can just browse the on-site Frank Lloyd Wright Preservation Trust’s gift shop for a flavour.

Chicago, USA © Rudy Balasko/Shutterstock

E M Forster referred to Chicago as «A façade of skyscrapers facing a lake and behind the façade, every type of dubiousness». A destructive fire in 1871 gave the city an opportunity to reinvent itself, and it grasped it with both hands. What came to be known as the Chicago School of architecture was the result, with early, relatively short skyscrapers adhering to the ‘form follows function’