Of Jazz, Art & the Mafia: The City of Chicago Will Blow Your Mind

These breathtaking photos of the Chicago skyline will make you want to visit the city.

The gorgeous Chicago skyline by night. (Photo Courtesy: Choose Chicago)

My hands are up in the air; I’m staring down the barrel of a gun and I’m not alone.

All my fellow passengers in the bus have stuck their hands up too.

Except, this is no hold up. It’s just Chicago’s most entertaining tour – The Untouchables.

It’s Chicago’s most entertaining tour – The Untouchables. (Photo Courtesy: Ashwin Rajagopalan)

I’m not big on organised tours and I wouldn’t have made the trek to Chicago, but for the dogged perseverance of my friend who lives up there. The Untouchables Mafia tour was almost the first thing I did after hopping off the plane. I’m a big mafia flick fanboy and the tour guides on this bus knew how to keep their audience under their spell even without their toy guns!

Andy’s is one of Chicago’s finest jazz venues, dating back to the 1950s. (Photo Courtesy: Ashwin Rajagopalan)

It’s not easy to spin tales when all the reference points around the city have been altered. Venues of bloody shootouts have become friendly neighbourhood retail establishments while the infamous brothels have all but disappeared.

But all that criss-crossing around Chicago’s historic streets where Al Capone and John Dillinger ruled the roost during the 1930s Prohibition era, also put the spotlight on Chicago’s skyline.

Andy’s, the jazz venue. (Photo Courtesy: Ashwin Rajagopalan)

New York might be the quintessential skyscraper city, with instantly recognisable icons like the Empire State Building – but I was amazed to discover that it was here in Chicago that the world’s first skyscraper debuted. The ten-storied Home Insurance building – they weren’t that tall back then – constructed in 1884, became the first building to use structural metal in its frame.

Chicago certainly doesn’t possess the maze of skyscrapers that dot the Manhattan skyline – but it’s the city’s Art deco buildings that set it apart. (Photo Courtesy: Ashwin Rajagopalan)

Chicago certainly doesn’t possess the maze of skyscrapers that dot the Manhattan skyline – but it’s the city’s Art deco buildings that set it apart.

These don’t just remind you of a glorious era but also hold their own among modern landmarks like the Willis (aka Sears) Tower and the John Hancock Center.

Art Deco, Demystified

It was celebrated architect Le Corbusier who first used the term Art Deco. (Photo Courtesy: Choose Chicago)

It was celebrated architect Le Corbusier who first used the term Art Deco.

Oddly enough, the term Art Deco gained popular usage only in the 1960s – despite the fact that the design style itself had taken off in the roaring 20s!

Art Deco became an expression against the grim and austere times of the First World War. It was characterised by smooth lines, geometric shapes and often gaudy colours. Expensive materials like silver, ivory and lacquer were all in the mix.

Regal Cinema in Mumbai is also an example of the Art Deco style. (Photo Courtesy: cinematreasures.org)

This luxurious design style finally hit a speed bump with the Great Depression of the 1930s. During its heyday, Art Deco was omnipresent from furniture to jewellery but it’s the architecture that has stood the test of time.

From Regal Cinema in Mumbai to the façade of London’s Arsenal stadium, Art Deco captured the imagination of architects and designers of an entire generation.

Jump on a Boat and Watch Chicago’s Modern History Unfold...

The Carbide and Carbon building that is now the Hard Rock hotel. (Photo Courtesy: Hard Rock Hotel Chicago)

Chicagoans call it the Champagne Bottle and it was almost the first building that caught my attention.

This is the Carbide and Carbon Building.

Designed by the Burnham Brothers, it was its golden top and pale green façade that prompted comparisons with a champagne bottle. I first spotted it from the river and then went to inspect the building up, close and personal.

The Hard Rock hotel. (Photo Courtesy: Hard Rock Hotel Chicago)

It is now Chicago’s Hard Rock hotel – but the incredible detailing from the Art Deco era is still intact. Very few cities offer a mix of waterways like Chicago – there’s the Lake Michigan and the Chicago river that intertwine, allowing you to capture great vignettes of the city’s fine buildings. The 75-minute-long Chicago Lake and River Architecture tour was probably the best time I spent in Chicago.

(A sundeck is so much more convenient than trudging the streets. Also? The guides on this tour share unbelievable passion for the city’s architectural landmarks... eventually – it rubs off on you.)

Merchandise Mart. (Photo Courtesy: Ashwin Rajagopalan)

The trivia didn’t stop coming when we crossed Merchandise Mart (home to Chicago’s entire wholesale business). This was actually the world’s largest building (till the Pentagon took over that mantle in the 1940s) and  probably the only building with its own dedicated ZIP code.

Sometimes skyscrapers in big cities are almost like faceless individuals, the type you will drive past without the slightest reaction.

Chicago River Tour. (Photo Courtesy: Choose Chicago)

One weekend in Chicago changed that.

I could almost visualise scenes from different eras playing out as I passed them... And more than once I wished for a rewind button that came with a pause.

Getting There and Around

Chicago’s O’Hare airport is one of America’s best connected for both local and international flights. It’s easiest to walk around downtown Chicago or hop on to a cab.

Accommodation

The W Chicago Lakeshore on the edge of the Lake Michigan offers stunning views and easy access to the city’s vibrant nightlife. (www.starwoodhotels.com)

(Ashwin Rajagopalan enjoys communicating across boundaries in his three distinct roles as a widely published lifestyle writer, one of India’s only cross cultural trainers and a consultant for a global brand services firm. Ashwin writes extensively on travel, food, technology and trends)