Located on the banks on Lake Michigan, Chicago’s jaw dropping skyline merits its reputation among the world’s most iconic backdrops.

Nicknamed The Windy City due to the icy gusts from Lake Michigan and colourful 19th Century tales of boastful politicians, the pulsating Midwest metropolis continues to play second fiddle to New York.

Our Travel Correspondent, Sharon Cain, and photographer, Steve Hare, set out to explore its eclectic offerings - and find out why it held Ol’ Blue Eyes in its thrall.

Lakeside Setting

The first sight of Chicago’s sensational skyline stopped us in our tracks - so much so we grabbed a coffee at the nearest lakeside bar to absorb its magnitude.

Dazzled by the sun-drenched skyscrapers as temperatures soared to a sweltering 30 degrees Celsius, the lakeside breeze and caffeine hit were most welcome.

Lake Michigan - America’s biggest lake which borders four states - is a magnet which effortlessly fuses beach life and city life.

With over two dozen beaches on the 26-mile picturesque lakefront, it was a perfect mid-week day for office workers to cool off with a dip.

Lunch could not have been any better - stunning scenery and sumptuous seafood while watching beachgoers dwarfed by shimmering buildings.

Birthplace of Modern Architecture

While Chicago strives to shake off its nickname as the ‘Second City’ to the Big Apple, nothing can diminish its reputation as the birthplace of modern architecture.

The city’s reincarnation was triggered by the famous fire of October 1871. Claiming hundreds of lives and decimating thousands of buildings, it caused over five billion dollars of damage in modern day currency.

The tragedy brought architects in their droves to redesign and rebuild the city, the most famous being Frank Lloyd Wright who dedicated two decades to inspiring and shaping its rebirth.

Chicago’s compelling legacy was brought to life for us on a 90-minute architectural river cruise- which puts the city’s formative role in architectural history into perspective.

The guide’s pride in his native home was infectious as he pointed out iconic buildings which include The Wrigley Building with its luminous white terra cotta façade.

Constructed in 1924 at the behest of chewing gum entrepreneur William Wrigley Jr. as a new company headquarters, it was awarded official status as a Chicago landmark in 2012.

Chicago By Night

While Chicago’s architectural delights are amazing by day, a sunset skyline sail at dusk is pure magic.

If you go on a Wednesday or Saturday evening between May and September, you can also enjoy a spectacular free firework display at the Navy Pier, near to where the cruises disembark.

We timed our sail to catch the display at 9pm on a Wednesday night. On Sundays, the fireworks start at 10pm. Also, when booking a daytime architectural tour, most operators offer a sunset trip for a reduced rate.

Conservation, Culture - and Cuteness

From skyscrapers to stingrays - Chicago certainly knows how to make waves and elicit ‘wows’ from its 12 million annual visitors, as we discovered at the Shedd Aquarium.

The immense aquarium in the animal care, conservation and education centre holds five million gallons of water, and is home to over 32,000 animals.

The biggest and most dynamic centre of its kind we had ever experienced, we loved every second. The endearing Californian sea lions included Tanner, who was rescued after being spotted devouring endangered salmon at a dam - and whose beaming smile was infectious.

If you visit, don’t miss the Stingrays being fed and the delightful displays from Pacific white-sided dolphins.

Heady Heights

Chicago’s ‘must do’s’ include ascending the Skydeck on the 103rd floor of Willis Tower - the world’s fifth tallest skyscraper.

Heady heights have never been my strongest point and my stomach lurched as I intrepidly tiptoed onto the glass floor which is rewarded by views of Chicago’s dynamic downtown.

On a bright day you can see for fifty miles in every direction to Michigan, Indiana, Illinois, and Wisconsin.

Running out of time, we raced through the Art Institute of Chicago whose 300,000 plus artworks include masterpieces such as Bathers at Asnières by Georges Seurat, and Nighthawks by Edward Hopper.

A bonus was the Institute’s touring exhibition Van Gogh and the Avant-Garde: The Modern Landscape. Based on the period between 1882 and 1890, it highlights the pioneering work of Van Gogh, Georges Seurat, Paul Signac, Emile Bernard, and Charles Angrand when the artists lived in villages on the outskirts of Paris.

City of Legends

Jazz, a long-standing tour de force in Chicago, is indelibly etched in the Windy City’s DNA.

While originating in New Orleans, another ‘must’ on the bucket list if you haven’t been, Chicago’s jazz legacy stemmed from a major migration of African Americans who headed here from the south in the early 1920s .

Classic icons made famous in Chicago include Louis Armstrong, Nat King Cole, and Ol’ Blue Eyes Frank Sinatra, who proudly extolled its virtues in My Kind of Town.

Depths of Downtown

Blues supremo : Morry Sochat

Deciding which jazz venue to head to on our last night wasn’t easy.

Our choice ranged from a venue where Al Capone and his mob used to hang out, a restaurant with accompanying jazz, a formal, theatre-style setting with conversation banned during sets - or a no- frills experience?

We opted for Rosa’s Lounge, hailed by USA Today as the ‘Best nightlife, Jazz and Blues Club.’

Two buses and a walk in the depths of downtown Chicago and we had arrived at a building which looked boarded up and distinctly shut. Giving the door an enormous push into a dimly lit, very welcoming down-to-earth bar, any misgivings vanished.

‘Wow’ Factor In Spades

The vibes and bar staff were great, drinks were cheap, and we settled down and waited for the talented blues supremos, Texan born Morry Sochat and The Special 20’s.

Influenced by the Chicago greats, their storming, high-energy, formula of singing (Morry is a powerful baritone), harmonica and knockout tap dancing blends Chicago Blues with Swing and 1950s Rock N’ Roll.

Rosa’s doesn’t sell food but allows visitors to buy tasty and excellent value authentic Chicago pizzas from a takeout up the road and eat them on the premises – the perfect finale to our full-on five-day adventure.

As we reluctantly ascended the skies from O'Hare airport, we looked down for a last glimpse of this charismatic, compelling city and understood why it kept pulling Ol’ Blue Eyes back home.


KEY FACTS
British Airways flies direct to Heathrow from London and Manchester
Architectural River Cruises include Architecture Tour Chicago, Chicago River Cruises, Chicago Ticket
Willis Tower
Shedd Aquarium
Art Institute of Chicago
Rosa’s Lounge