From its hit parade of architecture, art and that electrifying skyline, Chicago can’t fail to inspire. I hit the water on a Chicago Architecture Foundation River Cruise, onboard Chicago’s First Lady. It’s the one tour to rule them all. Not only are you served up a slew of prime vistas to fill your social feed, but the on-board narration is vividly brought to life by a foundation-certified expert volunteer guide. Our unscripted and unrivalled guide was Tom, a story-telling wizard who left us spell-bound over the course of 90 minutes, as he unfurled his rich tapestry of bite-sized insights on the city’s grand dames.

I felt like I was a taking a crash-course in architectural design, as we glided by all of Chicago’s defining period specimens, from neo-classical and art deco to modernism, post-modernism, new-modernism and adaptive re-use – currently all the rage as old riverside warehouses are internally gutted and repurposed for residential use. Drifting under downtown Chicago’s 34 bascule bridges, it’s the blockbuster buildings and the design giants behind them, that take pole position.

Emerging from the embers of the 1871 Chicago Fire, innovation was to the fore as Chicago sought solutions to make their rapidly-growing city more liveable. Parks and boulevards sprouted and the course of the Chicago River was reversed to stop Lake Michigan becoming so polluted. The warehouse behemoths of Fulton House and 600 West were some of the earliest skyscrapers, before the beloved Tribune and Wrigley buildings of the mid-1920s held court. Conversations soon turned to people’s respective pet picks, and it’s the Wrigley’s white terracotta tiled neo-Renaissance splendour that stole my affections.

I was also struck by the circular towers of 1967 Marina City building, endearingly nicknamed the Corn Cobs. This 61-storey twin tower complex must have been positively futuristic upon completion. The first fifteen floors are still used for car parking. At over 90 storeys high, the Trump Tower is one of the latest cloud-piercers to flank the riverfront, a gleaming blend of brawn and grace designed by the same architects behind Dubai’s Burj El Khalifa.

In this ultimate of look-up cities, I ogled building after building including that champion of contextualism, 333 West Wacker Drive. Opened in 1983, this building was lauded for its curved, shimmering, green-tinted façade, faithfully flowing in harmony with the river’s hue. In my hometown of Christchurch, the post-quake Deloitte building has done exactly the same thing, overlooking the Avon River. Tom remarked that the river’s distinctive green tinge is because of the algae and clay in the water.

I was also gripped by his insights on the river district’s substructure, where by many high-rise developers have had to dig 80 feet to reach bedrock, so they can secure the foundations. Much of the downtown district’s substrata is all “peanut and jelly”, with layer upon layer of clay. It’s the most inhospitable terrain for a forest of skyscrapers to be developed. All the more reason to marvel at the miracles of sky-high engineering, festooned with artistic flourishes.

After alighting from the head-turning cruise, I strolled down North Michigan Ave to Millennium Park. You’d be hard pressed to find two better specimens of insatiably engaging public art than Cloud Gate and Crown Fountain. The former is better known as The Bean, an ingenious stainless-steel elliptical sculpture, designed by Anish Kapoor. This whimsical, wondrous and reflective artwork acts like a tractor-beam for the selfie brigade, filling Instagram feeds the world over.

No matter what time of day, or the whims of the weather, Cloud Gate captures Chicago’s subtle mood shifts and skyline drama, including that great wall of buildings lining South Michigan Ave, with unwavering finesse. Just across the way, I was equally riveted by the video and water sculpture surrealism of Crown Fountain, which radiates a slew of local faces and spouts water from their mouths. In the thick heat of summer, the fountain’s expansive pool is a godsend for a cooldown. The 24-acre Millennium Park is a civic jewel, despite the lingering cloud of claims spanning corruption, bribery and cost overruns. I gazed over the glimmering stainless-steel ribbons of the Jay Pritzker Pavilion, designed by Frank Gehry and instantly reminiscent of his Walt Disney Concert Hall in Los Angeles. From a distance, it looks like the swirls of ribboning you attach to a gift.

Across the road from Millennium Park, I also ventured to the one-year old American Writers Museum. This little cultural gem is being showered with accolades for its engaging and interactive celebration of American writers, delving deep into their influence on American history and culture. The children’s section is equally compelling, showcasing the likes of Where the Wild Things Are writer, Maurice Sendak.

Strolling down to Grant Park, I transported myself to Paris at the Chicago Arts Institute, which famously boasts the world’s biggest collection of Impressionist masterpieces, outside of France.  I feasted my eyes on more than 30 paintings by Claude Monet, including a number of Water Lilies; Renoir’s Two Sisters; Cézanne's The Basket of Apples, Henri Matisse's Bathers by a River; and Vincent van Gogh's Bedroom in Arles and Self-portrait. Equally compelling is the Modern and Contemporary Art collection, headlined by Pablo Picasso's Old Guitarist, a stack of works by Andy Warhol and some fine pieces by Lichtenstein. Unmissable Chicago.

At the southern end of Grant Park, The Field Museum is celebrating its 125^th year, with a touch-friendly cast of dinosaurs joining the museum’s ranks. The Field has just unveiled the dinosaur “Maximo”, which you can stroke as you walk underneath his hulking belly. There’s also an enthralling exhibition running until January on Antarctic Dinosaurs, where you can follow The Field Museum scientists on their gruelling polar expedition to excavate remarkable dinosaur fossils.

As darkness fell, I jaunted back to the heart of Grant Park to swoon over the splendour of the 90 year old showstopper, Buckingham Fountain. You may well recognise it from the opening titles of Married with Children. Despite its vintage pedigree, it’s still one of the largest fountains in the world, sporting 134 jets. The fountain's hourly twenty-minute water display starts with small sprays, climaxing with a 46metre-high gusher. The animation is definitely best seen after dark, when the choreographed waterworks are accompanied with music and coloured lights. www.choosechicago.com

Chicago accommodation can be pricey, so you’ll definitely want to hunt down the best rates in your preferred location.  From cosy guest-houses to five-star hotels, Booking.com has nearly 500 accommodation options in the Windy City. Whether on the website or via the app, Booking.com is super easy to navigate with incredible deals and complete flexibility, if you need to amend or cancel your bookings. www.booking.com

Our intrepid national airline is setting its sights on the Windy City. From November 30, 2018, Air New Zealand will operate the new route three times weekly, year-round with its new configuration Boeing 787-9 Dreamliner aircraft. Flight time will be approximately 15 hours northbound and just over 16 hours southbound. One-way Economy fares between Auckland Chicago start from $1,019 (including taxes). Fares are also available via Los Angeles, San Francisco and Houston with onward connections to Chicago on partner airlines. Visit www.airnewzealand.co.nz  to book or for more details.

Mike Yardley is our Travel Correspondent on Jack Tame Saturday Mornings.