20 Years; 20 Places: No.20 Chicago
The last piece of the jigsaw. The list of 20 Places that have left an indelible mark on me is complete, and at no. 20 it had to be Chicago.
I started all this, picking 20 Players and 20 Places to commemorate me writing this Blog, that began life one warm June evening in my apartment in Chicago, 20 years ago.
Accompanied by just two suitcases I moved to Chicago in September 2003 and I knew little of the city except for a week I had spent there in the March of that same year.
Those early days were pretty tough on my own. I kept a diary, which morphed into this Blog really, and I struggled at first. There was a lot of soul searching, but I had a steely resolve and determination to make a go of it, and what awaited was my life’s biggest adventure.
Chicago is America’s best kept secret. Ask a Brit or a European to write a list of American places they would like to visit and Chicago would rarely make the top ten, yet it is truly one of the world’s greatest cities.
The city of tall shoulders as poet Carl Sandburg called it and home to the skyscraper, where the wind can blow hot and really, really cold. Lake Michigan as big as an ocean with beaches to add to the surrealism and the main artery of the snaking Chicago River on which I used to live (after owning it for 20 years I only sold my apartment last autumn).
Chicago’s many neighborhood’s each needing to be explored and the elevated train (the El) will take you there weaving high and around the city’s architecture.
The incredible museums and city parks including the elegent Grant Park and the stunning Millennium Park. Great theatre, and Chicago’s sports teams, one inspires the other frustrates.
The Magnificent Mile shops and the magnificent restaurant scene served by some of the countries most creative chefs. Great breweries and the Adler Planetarium and Shedd Aquarium.
The Ferris wheel on Navy Pier, the still free Lincoln Park Zoo, Lurie Gardens and the music scene. House, jazz, blues, opera and Lollapalooza – take your pick.
Endless opportunities. Endless discoveries. I miss Chicago every day. It was my kinda of town.
Chicago. Lived from 2003 – 2008.







As you may recall, I lived there at the same time – 2001-2012. I would move back in a heartbeat, if I wasn’t so happy here in Santa Fe.
Santa Fe is also a beautiful place to live I imagine.
This has been a great story, from 1 to 20. Thanks for sharing.
My pleasure Clive. Thanks for reading.
Great recap of your memories CA.
I’m visiting Chicago for the first time with work in July. Your shared experiences are certainly making me feel optimistic this will be a fun trip!
Apart from the work part anyway! 😜
You will fall in love with it. Will be hot. Enjoy.
I have visited Chicago around 20 times and love the place.
The first time was in the heatwave of 1995 (or was it 1996?) a work colleague had a friend who lived in one of the apartment blocks on the Gold Coast (it wasn’t one of the Mies van der Rohe designed one – but it was adjacent to it). she offered to take me on a trip around Chicago – was there anything I really wanted to see? So I got a fascinating trip early one Sunday around the south side as she pointed out the gang signs and told me which mob ran which which street. She was a former journalist on one of the Chicago newspapers (not the Tribune) and was a fount of knowledge on the place. If you are wondering why I was desperate to see the south side – it was used in the opening credits of Hill Street Blues which I loved as a kid. Although the programme wasn’t technically shot in Chicago a lot of the outdoors scenes were filmed there.
Besides that if time and the season permitted I would always try and get to a game at Wrigley Fields, although I once went to the Sox’s new stadium but it was a bit too concrete for me even if we had a box high up above third plate.
But other than that the music, the art galleries, the shopping, the architecture and the ambience were perfect.
Ah, you really captured the magic of Chicago! Nothing beats a summer evening walking through Millennium Park or catching a show in the Theatre District. And don’t even get me started on the food—every time I think I’ve tried the best deep-dish, another spot proves me wrong.
But I have to laugh thinking about you in Florida while we’re over here battling the latest ‘feels-like-negative-a-million’ wind chill. Enjoy your sunshine while we’re out here shoveling our cars out of street parking spots like it’s an Olympic sport. At least all this snow means less dirt getting tracked inside—until it melts, and then it’s a whole other mess. Trust me, scheduling a carpet cleaning in Chicago is a necessity this time of year!
Chicago really does stay with you, though. No matter where you are, it’s always ‘your kind of town.’
It is Tammie. Thank you for commenting.
You won’t find this funny, or true, but I actually miss the snow. Although not being out in it, but just watching it fall outside through the window 😊.