Stroll round the neighbourhoods
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.
Behold the skyscrapers
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’ maxim coined by Louis Sullivan. Things got bigger of course.
From Willis (aka Sears) Tower – said to have been inspired by cigarettes popping from a packet – to the Gothic silliness of Tribune Tower and wave-effect Aqua Tower, and from the iconic John Hancock Center to the corn cobs of Marina City, it costs nothing to crane your neck. One of the oddest high rises is Harry Weese’s 1975 Metropolitan Correctional Center – this is architecture that looks as if it could correct the very soul. To learn more, visit the Chicago Architecture Foundation, which includes a 320-square-foot scale model of downtown (viewing daily 9am-6.30pm).
Make the most of the free cinema and theatre
Throughout the summer months – June to October – the authorities lays on free film screenings in parks around the city, from contemporary to classic. See www.chicagoparkdistrict.com/events/movies for details. When they dry up, The Shakespeare Project of Chicago perform the Bard’s – and other dramatists’ – plays in public libraries from October to April.
Head to the Signature Room in the John Hancock building
If you can afford a drink, you might as well have it here, 95 floors up…
Meet the Greeters
You might be a little suspicious of people willing to sacrifice their time to show you round the city for free. But don’t worry – the only thing they want to convert you to is Chicago.
Try Millenium Park...
This could just be the city’s finest freebie, a 24.5-acre park dotted with monumental public art, from Jaume Plensa’s Crown Fountain, Anish Kapoor’s Cloud Gate (known locally as ‘The Bean’) and the peaceful Lurie Garden. Free concerts take place at Frank Gehry’s Jay Pritzker auditorium.
...or dive into the other parks
There are other more traditional offering than Millennium Park. Apart from its myriad plant and bird species, Chicago Botanic Garden allows for mile upon mile of skyscraper-free strolling, whilst Garfield Park Conservatory is now back up and running after a 2011 hail battering.
Then there’s the famed Lincoln Park Zoo, if you like zoos. If you don’t, head for the 1895 Lincoln Park Conservatory at its north end instead – the flowers really don’t mind being cooped up in its four handsome greenhouses (Orchid House, Palm House, Fernery, and Show House). For the really ruthless, the summer farmers' market is bound to throw up plenty of samples.
Over in Grant Park, from around April to mid-October, the 1927 Buckingham Fountain throws out an hourly water display – one of the world’s biggest – that lasts twenty minutes. Go for an evening show (until 11pm), when the water is accompanied by lights and music.
Board the L Train
OK, so this last one might not be strictly free but the orange line downtown towards Midway on the L is fantastic, giving the best view of the city’s buildings – a lot of bang for your buck.
What are your tips for enjoying Chicago for free?