IN 1885, the world’s first skyscraper, the 10-storey Home Insurance Building, was erected in Chicago.
Since then, the skyline has grown dramatically, with structures now looming 10 times as high.
“Downtown was our playground,” says 67-year-old Lynn Hughes, recalling her youth growing up in Oak Park, one of the city’s 77 neighbourhoods.
Back then, the 41-storey Prudential building reached furthest into the bright blue sky.
The former teacher is one of around 200 greeters, who volunteer their services to, in Lynn’s words, “show off our city”.
This is my first trip to Chicago, and as I settle in to my room overlooking Millennium Park, I can’t help but compare it to New York – a city which would be hard to knock off the No 1 spot, in my mind.
So why should people visit Chicago instead?
Lynn doesn’t hesitate before answering: “Our city is the friendly, clean, affordable New York.”
Millennium Park is one of Chicago’s many green spaces, situated within the sprawling Grant Park, known to locals as the city’s front yard.
Free activities range from weekend yoga classes on the lawn to classical music concerts performed by Grant Park Orchestra and Chorus in the Jay Pritzker Pavilion.
In summer, people gather around the Crown Fountain, made up of two 50-foot-high glass towers, featuring video projections of Chicagoans spouting water from their mouths, in the style of ancient gargoyles.
With so much on offer, Chicago is a year-round destination, and a new direct flight from Norwegian Airlines makes it cheaper than ever.
Plan a trip to delight the senses with these essential activities…
Do… a downward dog
The Windy City’s setting on Lake Michigan means Chicago truly has some spectacular views.
And while park yoga in the fresh air is enjoyable, striking the downward dog pose 94 floors high in the glass-walled 360 CHICAGO building is a thrill.
Sky Yoga is $15 (about £11), which also includes admission to the observation deck, Saturdays from 9am-10am.
Stay… at Athletic Association Hotel
This former men’s-only private members’ club – which had to keep its moniker as part of the deal to restore and re-open the Venetian Gothic building as a 241-room hotel – is an ode to old-world style, with its extravagant dark-wood interiors.
Overlooking Millennium Park, the Michigan Avenue building occupies an enviable location – it’s a short stroll from the likes of shopping mecca Macy’s, or the Art Institute of Chicago Museum.
Standard rooms cost from $269; suites from $1,000.
Eat… at RPM Steak
A few minutes’ walk from the riverside, this sophisticated restaurant on West Kinzie Street has an excellent variety of steaks, but save space for the sides, such as Japanese sweet potatoes and spicy broccolini.
RPM Steak frites is $43 (about £32); sides from $9-13 (around £6-10).
Enjoy… hilarious shows at Second City
The comedy club, which has been running for more than 50 years, sparked the careers of Bill Murray and John Candy, to name just two.
One of its current shows, Dream Freaks Fall From Space, is part-scripted, part-improv and takes a hilarious look at modern-day American life, from dating to the presidency.
Tickets to the show, which runs until October 3, cost from $23 (£17); alcoholic drinks from $7 (£5).
Listen… to the blues at Rosa’s Lounge
Dressed in a vibrant blue three-piece suit, 82-year-old Willie Buck sings classics such as Muddy Waters’ Mannish Boy.
One of several performers at the club, the grandfather of 20 is on first-name terms with most of the club’s patrons, who come here to see him play. Check the club’s calendar for dates.
Entry is from $10 (£7.50); cocktails $6 (£4.50).
Norwegian Airlines flies non-stop from London Gatwick to Chicago O’Hare from £149.90 one-way. See norwegian.com/uk or call 0330 828 0854.
For more on Chicago, visit choosechicago.com