Leave it to Donald Trump. In a city centre picturesquely clustered with one stunning skyscraper after another and countless rooftop attractions all competing for the best views of Chicago, there's something distinctively striking about the mega-mogul's 16th-floor patio at the Trump Tower.
Brushed with the golden glow of a sunset reflected from surrounding high-rises, the elegant Terrace at Trump may cower in comparison to taller hangouts, but with views shooting straight down the Chicago River into Lake Mead, gazing out from its glass edge feels almost like being atop a 16-storey cruise ship.
If the view is difficult to beat, the extravagant bar snacks are even harder to top.
Bacon cheddar cookies, cheese and habanero jelly and chilli lime cashews are the perfect accompaniment to summery cocktails, like the Rum Baby Rum.
Of course, in a city boasting glimpses of four states on a clear day - Illinois, Michigan, Wisconsin and Indiana - out-of-towners flock to anything with 360-degree views.
Add features like the Willis Tower's glass boxes - fiercely jutting 1.3m out from the 103rd floor Skydeck - and the Gotham-reminiscent building (the second-tallest in the Western Hemisphere) becomes a tourist hub in the sky as dusk settles.
Locals still refer to the Chicago icon as the Sears Tower, having been built as the company's headquarters in 1973.
Wanting a 110-storey structure that would withhold the city's renowned wind, architects derived a bundle tube design, clustering together 22sq m tubes to form thicker columns.
Go early to avoid the wave of anxiety that runs down the queue as the sun dips deeper, prompting panic that the photo opp is about to vanish into the horizon.
Likewise, don't fall victim to selfie compulsions like most of the visitors, who are too busy snapping away to glance down through the 3.8cm pane separating their soles from a 412m drop below.
Having seen Chicago from Trump's patio and Willis' Skydeck, I take in the view from the Peninsula Hotel's sun-soaked Shanghai Terrace, a dumpling-lover's haven serving varieties like lobster/chicken/black truffle, then head to Navy Pier for its ferris wheel perspective.
Soaring over Lake Michigan, below the landmark is a bustling mecca of kids eating candy floss, adults buying "to-go" margaritas before meandering down to the beer garden, families disembarking harbour cruises and couples wandering through the stained-glass window museum.
Such glass is prevalent through Chicago, particularly in Oak Park, home to many of architect Frank Lloyd Wright's famed houses.
"Art glass brings in nature in the form of light, but preserves a degree of privacy," says my Pedal Oak Park guide, leading cyclists through quaint, peaceful streets lined with impeccably manicured gardens, dashing squirrels and 22 Wright-designed structures.
Declared the greatest American architect of all time by the American Institute of Architects, Wright's childhood home was anything but lavish - thanks to a father who failed to support the family then eventually abandoned them - but just as his mother predicted while pregnant, Wright would go on to leave his marvellous mark on the world by "building beautiful buildings".
A key player in Chicago's architecture, Wright borrowed US$5000 ($7400) to buy his first property in Oak Park, which had become a growing hub following the 1871 Chicago fire, as city-dwellers searched for alternative areas to live.
Wright eventually left the suburb, running away with the wife of a client, but his works remain. Many reflect his Prairie School influences, like horizontal structures, intense geometric shapes and art glass.
The family returned to Chicago for a job in 1914, but his mistress and her two children perished after a servant set fire to their Wisconsin estate and fatally axed seven people.
From Oak Park scandal to the woman known for breaking Hollywood scandals we head to RPM Italian, owned by E! News anchor Giuliana Rancic and her Apprentice-winning husband Bill.
The eatery became the centre of controversy in the couple's reality show as the pair clashed over whether to open the restaurant in LA or Rancic's native Chicago.
Opting for Chicago has paid off. A second spot, RPM Steak, recently launched nearby and the original remains a local favourite, packed with couples, business executives and women complaining about life on a tour bus, even at 10pm on a Sunday night.
So what does Rancic drink when she comes to town?
An off-the-menu "Giuliana version of a Moscow mule", named the "G Fizz", a waiter tells us.
Immediately falling victim to the air of coolness that comes with ordering off-the-menu, I opt for another secret item - a refreshing gin and elderflower concoction.
Full of Mama DePandi's pasta, we step outside to a calendar-worthy array of firemen, perched GQ-style at firehouse 42 across the road.
It's a quiet night so the lads are chilling, happily taking photos with tourists while waiting for their next call-out.
Like many locals, the firefighters agree that one of the best parts of Chicago in summertime is not Millennium Park and its famous, mirrored "Bean" (aka Cloud Gate), but the city's diverse neighbourhoods.
Each offers its own unique vibe and the best way to see them is through a Greeter tour, escorted by volunteers who showcase their favourite spots, free.
"Downtown is beautiful, but it's not real," says my guide Gail Root, as we wander through the stained-glass dome at the Chicago Cultural Centre then under Macy's Tiffany vaulted ceiling.
"I always take people to at least one neighbourhood."
A 20-minute train ride brings us to Logan Square's Farmers Markets, where offerings range from frozen kale burgers and cocktail-flavoured ice cones to cardamom-flavoured granola.
Nearby Bucktown, named the "Midwest mecca of hipsterdom" by Forbes, remains a rapidly growing trend spot with cute boutiques, art galleries, bars hidden behind graffiti walls and music venues like the Double Door, which has hosted the Rolling Stones.
Across the street, teen girls queue for a gig at Subterranean.
Such diversity is what makes Chicago unlike many other big American cities, according to local Ely Garcia.
"You can have an upper-class place, then two doors down have a dive bar," she says.
"Each area doesn't just cater to a specific age group or pay check.
"You can go to any part of Chicago whether you're making a lawyer's salary or minimum wage, which is very different from what I've seen in New York, LA or Miami.
"Of course you still have snobby people, but for the most part we're very diverse, open and everyone just blends in, which makes it interesting to mingle."
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Hotel hotspot Thewit is in the heart of The Loop, with handy shopping nearby on State St and the outdoor oasis of Millennium Park. The hotel's roof lounge was named one of the top three rooftop restaurants in the world by Travel + Leisure.