Last October some friends and I took to the skies and flew to Chicago for a holiday. Having only been to New York before, I was excited at the prospect of trying somewhere new. Although for me, Chicago had big shoes to fill.
I was expecting a city like Manhattan in a lot of ways but maybe not quite as vibrant and exciting. How I ate my words folks. How I ate my words!
I came away feeling like I had a real connection to this mid-west metropolis. If you have never been before, I urge you to pack a suitcase immediately, book yourself into an Airbnb and go. You won’t be disappointed. Here’s why:
Chicago is not New York
If you had asked where in the world I would move to if someone held a gun to my head and said pick, a year ago I would have said New York. No question. I have been three times and there’s been nowhere I have visited that I’ve loved as much. I feel a traitor saying this but now I worship Chicago equally.
I visited twice in three months. Pretty much living on beans on toast to be able to cough up for another trip across the pond, tells you exactly how hard I fell in love. New York is quite different from Chicago. Chicago is much less intense than New York.
While having a plethora of tourist attractions, the hordes of people flocking to them is sparse in comparison. And these same people are pretty chilled too. No enormous queues for tickets and endlessly dodging people trying to take photos. No more coming away feeling stressed when you’re meant to be de-compressing from your life.
The streets aren’t as crowded. It feels more like you’re just meshing with the locals, sans visitors. The pavements are far cleaner too. I suppose this could be due to a more balanced number of tourists to tidy up after. On the whole, Chicago leaves you feeling more like you can breathe.
Speaking of Oxygen
This city has oodles of green space. If you’re someone who needs to spend time connecting with nature during a city break, then this is the place for you.
Lincoln Park was vast with gorgeous views of the Chicago skyline. Plus there is the added bonus of Lincoln Park Zoo! I’m a ginormous animal lover and had a blast here. And it’s free. Yes, free! This isn’t some petting zoo with an attitude either. It’s a full-sized, big enough to spend a full afternoon or longer, wandering and exploring type zoo.
We also took a trip to Millennium Park, which was romantic if you add a coffee and a walk during a lovely fall sunset. Filled with fantastic futuristic-looking sculptures and structures and pieces of art to muse over, this was a highlight for me.
If you walk over the bridge that connects the park to the Art Institute of Chicago, do me a favour and stop in the middle. On one side you will see an awesome view of the skyline. You will also see the famous Chicago loop train passing through the city. Then turn around. On the other side of the bridge you will be treated to an epic view of Lake Michigan. Two stunning views for the price of one.
When you’re not exploring one of these emerald gems, just walking through the city you will be enveloped by the beautiful tree-lined streets. They are in abundance. Magnificent to experience in the fall!
Architecture – It’s Everywhere
As mentioned earlier, Chicago is not New York and much of the architecture isn’t either. Many people are of the opinion that once you’ve seen one city, you’ve pretty much seen them all. I was more than pleasantly surprised when I went to the windy city.
A combination of past and present in the centre of town, there is always something different to see. In my opinion though the really stunning buildings are to be seen in the ordinary residential streets.
In the North, every house on every street is quite different. Eclectic as far as the eye can fathom. No cloning, build ’em fast and cheap, property developers have set foot here.
You can easily while away the hours wandering these amazing streets and see something different at every turn. The beauty is the detail though, so pay close attention.
The CTA – How I Love Thee
This may be a boring point to talk about to some but do not underestimate the blessing of a well organised, easy to understand, clean and cheap transportation system. The Chicago Transit Authority is all of these things. It’s also super-fast and reliable too.
As a self-confessed nerd of city transit systems (I know, shut up), I take note of these things. Let me assure you this is one of the best I’ve experienced so far.
Grab yourself a Ventra card, download the app to your phone, top up and off you go. You can also go old school and top up at a station if you prefer… like a savage, might I add.
Touch in, touch out on the card readers as you enter and exit and one, single cheap fare will be deducted from your Ventra account.
This single fare system was a revelation to a person who is used to being charged for distance. On the London underground, for instance, the further you go the more you pay. Trust me, the CTA system is much kinder on your bank balance.
Don’t rule out the bus system either. I’m a big fan of the train but wanting to be as efficient as possible I found that using a combination of the two was the best way to do this. Equally as reliable and fast as the train, I quickly became a big fan of the bus. Believe me, at home I haven’t taken a bus in years!
Culture, Culture, Culture
Chicago is a city that takes its art seriously. By art, I mean music, performance, visual, classic, contemporary, cutting-edge and everything in between. This is my city for art and art is my home.
There is much to see and do and experience during all seasons. Indoors and outdoors. I only dipped my toe in the Chicago art scene and I actually covered a fair amount of ground. This shows you how far Chicagoans take their culture.
I spent a full afternoon at the Art Institute of Chicago and managed to cover most of the enormous building. By cover, I mean I almost ran around the place, trying to take in as much as possible. I may as well have just eaten some of the pieces, I consumed so much.
It drips with every period of art and sculpture known to man. The place is incredible. I pretty much had an emotional breakdown when I realised I was staring at an original Van Gogh! Seriously, it was right there in front of me! What the hell man?!
Chicago is world famous for its music scene. Particularly blues. I enjoyed a fantastic night at the crazy cool Kingston Mines club in Lincoln Park.
I can’t recommend this place enough. Art murals and fairy lights adorn the walls and bars. Both bars seem to serve every alcoholic drink that ever existed, tempting you into a full immersion of the Kingston Mines experience.
This particular night The Mike Wheeler Band were performing. Funky soul was the order of the evening. The lead singer/guitarist came out into the crowd and pulled you right into the performance. In turn, the crowd were equally as involved and made the band feel loved. All these elements make for a fantastic gig.
The real highlight of the performance was the bass guitarist. The guy’s skills were insane. This man was born with a guitar in his hands and you could tell that he loves what he does. The whole band in fact. Go and see for yourself!
The real jewel in the crown for a night in Chicago though is a trip to the Green Mill in Uptown. This place bleeds history. Walking through the door you feel you have just stepped into a bygone era.
The Green Mill is known for being a regular spot for the likes of Al Capone and his mobsters’ during the prohibition era. It was also a hangout for Charlie Chaplin who worked on his silent films just a few streets away at Essanay studios.
On the night I visited, the band were playing swing music. Some patrons were dressed in 1920’s attire, which adds to that feeling of being in another place and time.
I watched a few YouTube videos on East Coast swing before my trip and now considering myself an expert (ha!) I got up to try my hand. I did my best but I was mostly useless. Pro-tip: – never wear brand new heels and try to swing. Ouch!
It was a hell of a lot of fun though. The Green Mill is a must do for a night of true magic.
The People – Charisma and Grit For Days
I fell in love with the people of Chicago. Unlike other cities, the folks here seemed calmer and more approachable. I didn’t have that uneasy feeling of being potentially unsafe or vulnerable as a tourist. Even while walking the streets alone late at night.
When asked for help or directions, the people were friendly and relaxed. Let me tell you Chicagoans are smooth. I was like a school-girl with a crush on the locals. What the hell was happening here?!
The thing I found most appealing about the people of this city though was their hard-line liberalism. They aren’t taking the shit that Trump is dishing out.
If I was him, I wouldn’t be in a hurry to visit Chicago. He definitely isn’t welcome in this town. And the people wouldn’t have a problem telling him that. God bless them.