Which of this city's classics would you try first — the famous hot dog, deep-dish pizza, or Italian beef sandwich?

DECISIONS, decisions, de- cisions. Should I go for the Italian beef sandwich, the deep-dish pizza or the hotdog with seven toppings?

Well, why not try all three? This is Chicago and these are the most famous delicacies of this amazing city. When in Rome and all that.

So, I do — and now I know why they call it the Windy City . . . 

I can take or leave the pizza, to be honest, although I enjoyed the sandwich. But the hotdog? Now that is a thing of beauty.

A chargrilled frankfurter in a bun with mustard, onion, sweet relish, tomato, pepper, dill pickle and celery salt. Oh, man.

Why seven toppings? Well, that came about after a 19th-century arms race between rival Chicago vendors.

They kept upping the ante by adding extra toppings to attract customers until it reached seven and everyone realized it was all getting out of hand, literally.

What you won’t get on your dog, though, is ketchup.

Chicagoans are so against this, hotdog sellers refuse to serve it. So don’t ask, not unless you want to be bundled into a cop car and driven to the city limits with a warning not to come back.

Chicago is having a bit of a moment.

It has won Best Big US City eight years running and is tipped to be one of THE places to go in 2025. It’s also been named America’s most walkable city.

And next year is the 100th birthday of Route 66, the fabled highway that starts in Chicago and heads west to LA.

From mobsters and blues singers to skyscrapers and food, there is so much to America’s third largest city, it’s hard to know where to start.

But my first impression is: God, Chicago is loud. You can barely hear yourself think in the Loop, the buzzing central business district.

That’s thanks to the clanking of the L (as in elevated) train, the metro that travels above the city centre streets on iron girders.

Rose from the ashes

Then there is the ear-splitting “nee-naw-paaaarp” of the fire trucks, which seem to be on constant call-out.

Chicago, Illinois? Surely, Chicago, ILLINOISE!

Still, better to be safe than sorry on the fire front. In 1871, most of the city, then largely wooden, burned down. But Chicago rose from the ashes — and then some.

This year is the 140th anniversary of the world’s first steel-framed skyscraper — The Home Insurance Building — conceived and built in Chicago.

Skyscrapers are to Chicago what jazz is to New Orleans or movies are to LA. Find out all about them on an architectural river cruise and prepare to be amazed.

Designing and constructing these cathedrals of the skies took vision, genius and bravery — particularly considering Chicago was built on swamp land next to Lake Michigan.

And all the different styles blend together. From gothic stone, art deco marble and chrome to sleek, futuristic glass, nothing looks out of place.

Once you have marveled at these leviathans at ground level, head to the Willis Tower, the tallest in the city, and take the lift to the SkyDeck glass observation platform on the 103rd floor — 1,353ft in the air.

And do look down. You won’t forget that view in a hurry.

You could say Chicago is largely responsible for another source of noise, too — rock music.

Southern blues singers such as Muddy Waters and Howlin’ Wolf fled segregation to seek their fortune in Chicago.

There, they invented the exciting, electrified blues that, in the early 1960s, grabbed the attention of Brit bands like The Rolling Stones and Led Zep.

Much of this amazing music was made at Chess Studios — the Abbey Road of blues and now a museum.

In this unassuming building on Chicago’s South Side, magic was made — inside a room smaller than the office of the Chess Brothers who owned the place.

All the original features are still there. Well, apart from one — the glass frontage.

Little Walter, a fantastic singer best described as “difficult”, got in a beef with the Chess Brothers over money — and drove his car through the window.

The music is still going strong, though, thanks to clubs like Buddy Guy’s Legends, owned by the last living Chicago blues great.

Before the Sixties blues boom, to most Brits Chicago simply meant gangsters. The city still takes a perverse pride in their activities.

Take the Mob coach tour and see the alleyway next to the Biograph Theater where, in 1934, bank robber John Dillinger was shot dead by cops after watching a movie . . . about gangsters.

You will also visit the site of the 1929 St Valentine’s Day Massacre and the favorite hangouts of Mob boss Al Capone and his lieutenant, Frank “The Enforcer” Nitti.

The Mob ran the city’s speakeasies — illegal bars offering booze during the 1920s Prohibition.

Get a taste of this life at the retro Chicago Magic Lounge, a “secret” nightclub hidden in a launderette.

The highlight is magicians doing sleight-of-hand tricks at your table — another Chicago innovation, designed to keep thirsty audiences entertained until the booze was served. There is much more to Chicago’s food than those hotdogs and pizzas, too.

The city has a burgeoning reputation as a foodie paradise. I loved Perilla, a Korean American Steakhouse which, as luck would have it, was in my hotel, the smart L7 By Lotte in Wabash Avenue in the Loop.

And head to Pilsen, Chicago’s Mexican district, for a walking tour of bars, restaurants and takeaways. Chicago has one of America’s largest Mexican communities, and its influence looms large. Here you can try chilli margaritas, pulled pork, tortillas and the Mexican specialty, tamales — meat or veg wrapped in dough then steamed in a corn husk. It’s an Aztec creation that may well be the world’s earliest fast food.

I’m barely scratching the surface of what Chicago can offer as a holiday destination.

There isn’t enough space to talk about the welcome peace and quiet of a stroll in beautiful Millennium Park, enjoying the hot October sunshine on the beach by Lake Michigan, the endless opportunities to shop on the high-end Magnificent Mile, or taking in the great bars and restaurants on the riverside walk.

Suffice to say, Chicago is endlessly fascinating — and everything I hoped it would be.

It may not have the big-hitter tourist attractions of, say, New York, but it’s unpretentious, friendly, exciting and very welcoming.

As Frank Sinatra sang: “Chicago is one town that won’t let you down, it’s my kind of town.”

Bang on, Frank.

The Sun  UK