13 December 2021

Chicago: Skyscrapers, speakeasies … and all that jazz

13 December 2021

I’m sitting on a ledge, but not just any old ledge, The Ledge. This ledge is a petrifying prospect, a glass box attached to – and sticking out 4.3ft from – the world’s eighth tallest building, 1,353ft up.

Not for those with vertigo, but an Instagrammer’s dream, the most terrifying moment of being 103 floors up on the Skydeck (theskydeck.com) of the Willis Tower (formerly known as the Sears Tower) in downtown Chicago is stepping on to The Ledge, even though I’m assured it can hold 10,000lbs.

Inching my way on to the thick glass platform looking anywhere but down, the fear of falling gradually dissipates as my eyes veer towards the immense vista of Chicago, over skyscrapers which seem pint-sized compared with this one, the wide highways snaking towards Lake Michigan.

Hannah Stephenson on The Ledge at The Skydeck, Chicago (Hannah Stephenson/PA)

On a clear day, I’m told, you can see four states – Illinois, Indiana, Wisconsin and Michigan. But even today, when the sky is swathed in cotton wool cloud, it’s a spellbinding sight. There are currently four ledges to accommodate visitors – you’ll only get a minute on The Ledge for those photos – but a fifth one is planned for spring 2022.

It’s one of the many attractions of the ‘Windy City’ – a sea of skyscrapers and speakeasies – often seen as second to New York, but with all the buzz of the Big Apple and none of the brashness.

I visit shortly after America has opened its doors to UK visitors and they’re  cautious– all wearing masks on public transport and in indoor public places – yet it still feels happily busy.

People taking photos at Cloudgate, known as ‘the bean’ (Adam Alexander Photography/Choose Chicago/PA)

The West Loop restaurant scene is a hive of activity on a week night, when you won’t get a table if you don’t book. Theatres are once again filling up, albeit with mandatory mask-wearing throughout performances.

In Millennium Park, The Bean, aka Cloud Gate, a shiny kidney bean-shaped stainless steel sculpture by Indian-born British artist Sir Anish Kapoor – and one of Chicago’s flagship architectural landmarks – is continuously awash with people taking selfies against the strange curved reflections of the skyscrapers.

Chicago life is back.

Look up to find your bearings from lofty landmarks such as the art deco Wrigley Building with its elegant clock tower on the famous Michigan Avenue, the neo-Gothic Chicago Tribune giant, now sadly no longer inhabited by newshounds but converted to luxury condos (known as Tribune Tower), the corn-on-the-cob towers of Marina City and the imposing glass Trump Tower condo hotel, a giant thumbprint in the heart of the city.

(Choose Chicago/PA)

At night it’s even more exciting, thanks to a glittering skyline of mile-high edifices, neon theatre lights and twinkling cruisers conducting night-time tours on the Chicago River.

The old heavy steel bascule bridges are occupied by trundling overhead ‘L’ trains, the city’s elevated train system which began running in 1892 and still carries more than 700,000 riders daily through its patchwork of neighbourhoods, weaving between the vast glass giants.

Of course, there are tours for whatever your interest – the popular boat tours will tell you how the river flow was reversed during the Industrial Revolution to keep the pollution out of Lake Michigan and divert the city’s filthy wastewater inland to the Mississippi River.

It’s from the water that you get the best view of the architecture and the bridges, the art deco builds of the early 20th century which rub shoulders with the post-modernist glass towers of the 1980s. Guides will fill you in on Chicago’s great fire of 1871, its meat-packing history and its tradition of dyeing the river green for St Patrick’s Day.

Happier on terra firma? There are walking tours for anyone interested in Chicago’s famously chequered past – from Al Capone gangster excursions to movie walks, taking in Ferris Bueller’s Day Off, The Dark Knight (when Chicago became Gotham City) and Spiderman 2.

The magnificent mile, running from Michigan Avenue downtown all the way to the shore of Lake Michigan, gets classier the closer to the water you get, with designer shops including Burberry and Gucci fringing the sidewalks as you step nearer to the beach.

The Chicago CityPASS (citypass.com) will save you money if you’re a first-timer wanting to do the main attractions including the Art Institute of Chicago, the Shedd Aquarium and the Field Museum, while the Adler Planetarium is due to reopen in March 2022 and will also be included in the ticket.

These are the staples of any first visit…

Skydeck Museum (theskydeck.com)

The Ledge at The Skydeck (Ranvestel Photographic/Choose Chicago/PA)

In a web of corridors at ground floor level, this newly added compact museum which opened in April offers an easy-to-follow precursor to the Skydeck ascent – and gives the visitor juicy bitesize snippets, from the great fire and rebuilding of the city, to the fact that lightning strikes the Willis Tower anywhere between 50 to 100 times a year.


Chicago isn’t only famed for its deep dish pizza – Lou Malnati’s (loumalnatis.com) is the real deal – and hotdogs (there are more hotdog stands in Chicago than McDonald’s, Burger King and Wendy’s combined). If you’re after a real Chicagoan dog, Portillo’s (portillos.com) is one of the originals, but never ask for ketchup. It’s sacrilege.

New upmarket eateries are springing up in the West Loop district, where Oprah Winfrey made her mark when she arrived in 1989 and based her famous show from 1990-2011.

Rose Mary (rosemarychicago.com) an airy new restaurant with high ceilings, whitewashed brick walls and honey-coloured oak tables, encourages its diners to share platters of the mixture of Italian-meets-Croatian dishes, including cold roasted beets with pistachio and honey, duck sausage, squid ink risotto and a variety of imaginative ways with pasta. They advise booking 60 days in advance.

The Time Out Market (timeoutmarket.com/chicago) across the street, which opened shortly before the pandemic and has recently re-opened, is an eclectic mix of gourmet food outlets serving everything from caramelised chicken dumplings to artisan chocolates, which lunchtime diners devour at high tables in the centre of the building.


Want to play pinball in a cool vintage arcade bar serving craft beers with names like Rind Over Matter and Hell Or High Watermelon, strong cocktails and Red Light Green Light shots as a nod to Squid Game? Replay (replaylincolnpark.com) in Lincoln Park is the place to go.


It wasn’t only Sinatra who thought Chicago was ‘My Kind of Town’ – the city is awash with blues and jazz bars, influenced by the Great Migration of African Americans in the early and mid 20th century from the southern states of Mississippi and Louisiana, who moved to Chicago because of its rich railroad, meatpacking and manufacturing industries.

Among the most famous of the jazz haunts is Green Mill (greenmilljazz.com), a cosy jazz club reputedly frequented by gangster Al Capone whose regular table nudged the smallish dance floor and offered the best view of the band. Today, locals prop up the bar while – for an entrance charge of $15 (cover charges vary depending on the act) – tourists try their luck to nab a booth. No reservations. Cash only.

Cool neighbourhoods

(Jamie Kelter Davis/PA)

Dubbed the ‘coolest neighbourhood in the US’ by a Time Out reader survey, Andersonville, on Chicago’s north side, is now home to one of the city’s largest LGBTQ+ populations and has a laid-back, bohemian atmosphere focusing on community, pride and sustainability. Its streets are lined with quaint and colourful independent shops including a comic book store and fair trade pop-ups.

Entertainment? Venture into a laundromat, where a hidden interior door opens up to The Chicago Magic Lounge (chicagomagiclounge.com) a speakeasy magic theatre and bar, where table magicians show you their sleight of hand skills close up.


Hannah Stephenson was a guest of Choose Chicago (choosechicago.com) and stayed at the Pendry Chicago (pendry.com/chicago). Room rates start from $166 (approx. £125) per night for a king guestroom. British Airways (britishairways.com) flies London Heathrow to Chicago, from £425 return including taxes and charges.

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