Why Chicago plays second fiddle to New York remains a mystery following a whirlwind blast in America’s Windy City.
Far from living up to its name, we melted our way through the city’s eclectic cultural offerings as the thermometer soared past one hundred degrees Fahrenheit. Thankfully respite came from the welcome breeze on a sensational architectural river tour and sunset cruise.
Join us on our adventure - and find out why Ol Blue Eyes said it was his kind of town which made him ‘grin like a clown’.
Designs on Success
The skyline is a testimony to ingenuity and creativity.
While Chicago constantly strives to shake off its title as ‘Second City’ to the Big Apple, nothing can diminish its compelling legacy as the birthplace of modern architecture.
Chicago’s reincarnation was triggered by the famous fire of October 1871, which raged relentlessly for three days.
Claiming hundreds of lives, it decimated thousands of buildings and caused over $200 million dollars (over five billion dollars in today’s equivalentt.) in damage.
The tragedy brought architects in their droves to redesign and rebuild it, the most famous being Frank Lloyd Wright. Hailed as among the world’s most talented in his field, he dedicated two decades to inspiring and shaping the city’s rebirth.
Iconic: The Wrigley Building is key to Chicago’s urban growth.
Chicago’s back story was brought to life for us on an architectural river cruise where we were mesmerised by the gleaming, impressive buildings while learning about the city’s formative role in architectural history.
The guide tour’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
Stunning sunsets.
While the architectural delights are amazing by day, they are beyond beautiful on a sunset skyline sail.
When you book a daytime architectural tour, most operators seemed to offer a sunset trip for a reduced price.
Dazzling display of fireworks at Navy Pier
If you venture on a sunset cruise on a Wednesday or a Saturday between May and September, you can watch a spectacular display of fireworks for free at the Navy Pier which is close to where the cruises disembark. Starting at 9pm on a Wednesday and 10pm on a Saturday, they are electric.
Lakeside Setting
Sand and skyscrapers: views over Lake Michigan.
Chicago’s location on Lake Michigan - one of America’s five great lakes which borders the states of Illinois, Indiana, Michigan and Wisconsin - effortlessly fuses beach life and city life.
Over two dozen beaches are among the highlights of a 26-mile picturesque lakefront – perfect for office workers to have a refreshing lunchtime dip.
Lunch doesn’t get better when sampling seafood and observing beachgoers dwarfed by the shimmering buildings.
Heady Heights
Sittin’ on top of the world: Chicago Skydeck
Among the absolute ‘must do’s’ is ascending the Skydeck on the one hundred and third floor of the Willis Tower which dominates the Chicago skyline and is the world’s fifth tallest skyscraper.
A glass floor affords stomach lurching views of the city and streets below. On a clear day you can see for fifty miles in every direction across to Michigan, Indiana, Illinois and Wisconsin.
A major revamp in 2021 included an interactive museum relaying Chicago’s proud history and sense of identity.
Water Shedd
Rescued sea lions at The Shedd Aquarium.
Chicago certainly knows how to make waves. We immersed ourselves in the Shedd Aquarium whose five million gallons of water is home to over 32,000 animals which include 1,500 species of fish and mammals.
We found the Californian sea lions, three of whom are rescues, particularly cute. Our favourite, called Tanner, had been rescued after being spotted devouring endangered salmon at a dam. His beaming smile was infectious.
Making a splash: Pacific white sided dolphins.
A packed daily programme includes Stingrays being fed and delightful displays from Pacific white-sided dolphins.
From manatees to Masters, Chicago has it all. We loved The Art Institute whose 300,000 plus artworks include Bathers at Asnières by Georges Seurat, and Nighthawks by Edward Hopper.
A bonus was the 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, has been indelibly etched in the Windy City’s DNA.
While originating in New Orleans, an absolutely 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 himself, Frank Sinatra, who proudly extolled its virtues in My Kind of Town.
Depths of Downtown
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
High Octane: Morry Sochat and The Special 20,s.
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 amazing (in taste and price) authentic Chicago pizzas from a few doors up the road and consume them on the premises – the perfect finale to our full-on five-day adventure.
On a major high, we didn’t need a plane to fly to our next adventure in Washington.
As we reluctantly jetted off from O Hare airport, we understood how this compelling city kept pulling Ol' Blue Eyes back home.
