A Romantic walk through the streets of Chicago
I have spent over 25 years working with film and television so imagery is something that plays a large part in my life.

There is no country in the world where visual mediums have done more for to promote than in the US. In many ways if you are a lover of films and contemporary culture, you might feel you know many parts of the US, even without setting foot on American soil.
I recently visited Chicago for the third time and wanted to spend a day gently meandering the streets, getting a feel for this visually iconic city.
An English Gentleman walked out of his hotel to get a feel for Lake Michigan ….walk through uptown, find a beach, go up high to see the city, eat a fancy lunch, meander through luxurious shopping streets, have a beauty treatment, chat with some locals during dinner and then finish the day at one of the cities finest rooftop bars.
Chicago is the third most populous city in the United States, after New York City and Los Angeles. With 2.7 million residents, it is the most populous city in both the U.S. state of Illinois and the American Midwest with a population of over 2 million (9.5 million people in the Chicago area)
In 2012, Chicago hosted 46.37 million international and domestic visitors, an overall visitation record.
Phrases such as “Windy City” and “Second City” Chicago should definitely be on your bucket list.
Chicago is a city of a 100 views and so much more and what’s more is a perfect city to walk around, which for a Londoner is fantastic as I think walking is the best way to see a city, which is exactly what I did. Dressed in shorts, a t shirt, hat and sandals I went out to explore.
Starting in the South Loop

Walk into Grant Park

Then to Buckingham Fountain
While in operation, every hour on the hour for 20 minutes the Fountain produces a major water display and the centre jet shoots 150 feet into the air.

Walk along lake shore drive heading north

The walk along the shoreline is not only a wonderfully relaxing one but a great place to people watch from power walkers to smoochers to business men and its really very quiet, with no crowds.
Walking up over the Chicago River which is not particularly tourist friendly at present (though this area was being refurbished) but the iconic looking American steel bridge will remind you of a million us cops/action movies.
From River Esplanade Park
Walk through Gateway Park to Navy Pier which was having a major face lift last year.
I love Navy Pier as it reminds me of pure no nonsense American fun.
It makes me think of Coney Island, Bruce Springsteen and iconic American seaside towns.

Continuing up the shoreline north to Olive Street Beach which from a visual juxtaposition is amazing, in that one way is sand and golden water and the other way cars and skyscrapers.

Walk along the concrete path as again this is full of locals and not tourists, walk through the subway and you will then be in medical, arty and student land (all situated in a beautiful part of the city). Immediately I felt I was in Harrison Ford’s film “The Fugitive”, and upon research I was right as many of the films locations were in Chicago, as well as Harrison himself being Chicago born.
Past the Museum of Contemporary Art

to the former John Hancock Observatory now 360 Chicago

Time to switch direction as my afternoon was going to be high end fashion and luxury inspired.
Lunch was refined, quiet and upmarket at Pelago
A crisp glass of red wine, lamb with pudding and coffee. It was a perfect place to change pace, be looked after and pass a very pleasant hour.

Then round the corner to Oak Street, Chicago’s premier shopping street for luxury and fashion. Very chichi with all your big names from Tom Ford to Christian Laboutin, all set in a very beautiful tree lined road with trailing plants, which is evident on lots of Chicago’s streets, giving the cities shopping district a very pleasant feel.


From Oak Street you have Chicago’s famous Magnificent Mile on Michigan Avenue
If you think where the ladies from Sex and The City might like to shop, eat, chill and party then you are on the right tracks….. Burberry, Victoria Secrets, Ferragamo ….
I strolled south towards midtown and The Chicago River
Dropping into The Dana Hotel Spa (660 North State Street)
for a manicure & pedicure. It’s a funky boutique hotel where I got to have a long chat with a real Chicago lady who looked after my nails.
After this I dropped by The Langham Chicago which though I did not stay there would be my recommendation. As with all the Langham’s I have visited it looked fantastic and definitely that touch of English luxury away from home made me feel very calm and at ease.
For a true experience I would definitely head down to The Purple Pig. Situated on the edge of the river at the southern end of The Magnificent Mile I loved this. I had tried to get in when I visited in 2013, and was passing so as luck would have it, they had 1 seat tucked up the bar, which I love, in the mix, by the chefs. Full of atmosphere. High end casual is how I would describe it. It had a youngish cool but friendly crowd, great service and good food.
My advice would be to head round the corner to end your evening for cocktails up The Trump Tower at The Terrace looking out to sea….

Travelling from London
Our chauffeur service was perfect and would thoroughly recommend. I travelled Virgin Upper Class (read our review here) which I would also have no hesitation in recommending, especially if you travelling from London Heathrow as their First Class Lounge is excellent.
