Flying in Style with United Airlines The trip began exactly as any holiday should – with someone else handing me a glass of something cold whilst I settled into my Business Class seat.

nited Airlines hosted our flights to Chicago and the experience couldn't have been smoother. Comfortable seats, excellent service and the chance to arrive refreshed rather than resembling a crumpled piece of hand luggage is always a win in my book.

Our Home in Chicago: RIU Plaza Chicago For our stay, we checked into the RIU Plaza Chicago, which I have to say was a real surprise in the best possible way.

Modern, stylish and perfectly positioned just off the Magnificent Mile, it felt like the ideal city hotel. The rooms were spacious, the views were superb and everything was within easy reach. For clients looking for a quality hotel without venturing into eye-watering luxury pricing, this is exactly the sort of property I'd be recommending.

Behind the Scenes at United HQ

One of the more unique experiences of the trip was a private tour of United Airlines' headquarters.

As someone who spends their days helping clients navigate the world, it was fascinating to see the operation behind one of the world's largest airlines and hear about some exciting plans for the future. Whilst I can't reveal all the details, it's fair to say there are some interesting developments ahead.

Skydeck Chicago & Conquering The Ledge

No first visit to Chicago would be complete without heading up the Willis Tower to experience Skydeck Chicago. The views are extraordinary. From the 103rd floor, the city stretches endlessly in every direction, with Lake Michigan looking more like an ocean than a lake.

Of course, there's one reason most people visit Skydeck: The Ledge.

For anyone unfamiliar, this is essentially a glass box extending out from the side of the building. You step onto a transparent floor and look straight down 1,353 feet to the streets below.

I can confirm that your brain knows perfectly well the glass is safe. Your legs, however, are not always convinced.

Terrifying? Slightly.

Worth it? Absolutely.

Wrigley Field: Baseball, History & An Exceptional Dessert Trolley

That evening we headed to one of Chicago's most famous landmarks – Wrigley Field.

Even if you're not a baseball fan, this place is special. Opened in 1914, it's one of America's most historic sporting venues and has a charm that's difficult to describe until you're sitting there experiencing it.

One of my favourite details was the famous hand-operated scoreboard, which has been manually updated since 1937. In a world where everything is digital, there's something wonderfully nostalgic about seeing a tradition like that preserved.

We watched the Chicago Cubs from a private suite, which was every bit as enjoyable as it sounds. Fantastic views, excellent hospitality and enough food to feed a small village.

The undisputed MVP of the evening, however, was the dessert trolley.

Forget the baseball.

Bring me the trolley. And that cheesecake.

Whilst there, I also learned another important Chicago food rule. If you order a Chicago-style hot dog, whatever you do, don't ask for ketchup. Chicagoans are fiercely protective of their hot dogs and firmly believe ketchup has no place anywhere near one. Mustard, relish, onions, tomatoes, pickles, sport peppers and celery salt? Absolutely. Ketchup? Not a chance.

Meeting "The Bean"

Our second day began with a visit to perhaps Chicago's most photographed attraction: Cloud Gate, affectionately known by everyone as "The Bean".

Designed by artist Anish Kapoor, the enormous mirrored sculpture reflects the city skyline in every direction and somehow manages to look different from every angle.

It's one of those landmarks that sounds a little underwhelming on paper but is genuinely brilliant when you're standing beneath it. Watching the skyline curve and distort around you makes for some fantastic photographs and a great introduction to Chicago's impressive architecture.

A Private Tour of the Art Institute of Chicago

This was one of those experiences that will stay with me for a very long time.

Thanks to Choose Chicago, we were fortunate enough to enjoy a private tour of the Art Institute of Chicago before it opened to the public.

Standing in front of original works by Monet, Renoir and Van Gogh is impressive enough.

Standing in front of them without crowds, without queues and in complete peace is something else entirely.

There was a moment standing in front of Monet's work when I realised there wasn't another visitor in sight. Just us, the guide and some of the most important paintings ever created.

For art lovers, this is a genuine bucket-list experience.

Deep-Dish Pizza: A Battle We Lost

After all that culture, it was time for one of Chicago's most famous exports.

Pizza.

Or more specifically, deep-dish pizza.

Our stop was Gino's East, where we tackled Chicago's famous cheese-filled, sauce-topped masterpiece.

Now, I'd like to tell you that I conquered multiple slices. 

I'd like to tell you that I represented Britain with distinction.

Unfortunately, after one slice, I realised this wasn't really pizza.

It's more of a delicious, molten cheese pie disguised as pizza.

Magnificent? Yes.

Defeatable? Absolutely not.

Museums & An Architecture Tour Like No Other

Our final day combined two of Chicago's greatest strengths: culture and architecture.

The city's museums are genuinely world-class, but the standout experience was undoubtedly the famous architecture boat tour.  I've done boat trips in plenty of cities around the world and this may well be the best.

Cruising along the Chicago River provides a completely different perspective on the city. The guides bring the skyline to life with stories of innovation, ambition and architectural brilliance whilst you're surrounded by some of the most striking buildings in North America.

Even for those who don't normally get excited about architecture, it's difficult not to be impressed.

Why Chicago Might Be America's Most Underrated City

What struck me most about Chicago was how effortlessly it combines everything travellers want.

World-class dining.

Museums and galleries that rival anywhere in Europe.

A beautiful waterfront.

Historic sporting venues.

Outstanding shopping.

And perhaps most importantly, a warmth and friendliness that makes visitors feel instantly welcome.

For clients looking for something a little different from New York, but still wanting that iconic American city experience, Chicago is an easy recommendation.

It's sophisticated without being pretentious, exciting without being overwhelming and packed with experiences that appeal whether you're travelling as a couple, with friends or as a family. I arrived expecting a great city break.

I left wondering why more people aren't talking about Chicago.

A huge thank you to United Airlines and Choose Chicago for their hospitality, generosity and for showing us the very best of this remarkable city. Chicago has firmly earned a place on my list of favourite American cities - and I suspect it might just do the same for all of you.