Four Days in Chicago: A Whirlwind Trip to the Windy City {Part One}

Back at the start of July 2022 I spent four days in Chicago for ClickAway, a photography conference run by Click Community.  It was my second time attending – my first was ClickAway Atlanta back in March 2020, right before the world shut down (quite literally – I landed back home in the UK just two days before all flights were grounded, schools closed and lockdown was initiated).

I hadn’t been on a plane since then so my first post-pandemic international flight was definitely a good one to re-initiate me into the world of travel: four days in Chicago for a whirlwind trip to the Windy City!



I had a total of four days in Chicago with only relatively limited time to explore in between ClickAway photography classes.  I 100% intended to make the most of it and wanted to see as much as I could in the short amount of time that I had.  I went prepared with a long list of things I wanted to do whilst I was there, knowing full well that I wouldn’t ever be able to get through them all but also knowing that I’d have a damn good try.

Here’s what I ended up getting up to…



I stayed at my Mum’s house the night before my journey so I could get a lift to the airport for my morning flight rather than tackling trains and tubes with my suitcase.  I was hoping for a reasonably smooth re-introduction to flying abroad (because despite absolutely loving travelling I do tend to get quite anxious before a trip, flights in particular).  Of course my plane ended up being delayed for two hours *eye roll*.

Normally this wouldn’t bother me too much – I’d simply go and mooch about the airport, grab a hot chocolate etc… However, the smooth-talking man on the tannoy very matter of factly informed all of us patiently-waiting passengers that the reason for the delay was that the plane we were due to be flying on had been hit by lightning on it’s inbound flight and that it needed checking over and some urgent engineering works to be administered to make sure it was safe to fly.  Not really what you want to hear before an eight-hour flight!

Thankfully the flight itself was pleasant enough and drama-free.  I had a just-chatty-enough-without-being-too-chatty neighbour (and an empty seat in between us), I watched a movie, did some writing and whilst it felt long & boring as transatlantic flights always are, it was ok.

After waiting in queues for hours to get through security and baggage reclaim (O’Hare Airport was a nightmare!), I successfully managed to navigate the L-Train to downtown Chicago and then promptly got lost wandering the streets trying to find my hotel – the Fairmont Chicago Millennium Park.  When I eventually located it (in typical Chloe fashion I’d basically walked in a big circle all the way around it) and checked in, I was absolutely exhausted. I’d planned to head out to explore locally but my body had other ideas and I pretty much fell into bed.  Eighteen hours of travelling will do that to a girl!

Obligatory aeroplane window view, somewhere over Canada

Arriving at my hotel – the Fairmont Chicago Millennium Park

My room was great – I was on the 29th floor and the views were pretty special.



The first day of ClickAway Photography Conference and I had a full-on day of seminars, shooting classes and events so I didn’t think I was going to get any real chance to explore Chicago.

However, jet lag meant that I was awake super early so I took full advantage of it and headed out to see Millennium Park first thing in the morning before the rest of the world was awake.  It was only a five minute walk from my hotel.

I started at Lurie Garden, a serene and pretty spot full of colourful wildflowers and water features nestled in amongst the skyscrapers.  Well, it would have been serene if I hadn’t been attacked by the red-winged blackbirds that were apparently nesting nearby.  There were warning signs up that the birds can be quite protective and territorial but I certainly wasn’t expecting to be viciously dive-bombed multiple times – I can confirm that their claws and beaks are sharp!

Lurie Gardens

Once I’d escaped from the birds (and emotionally recovered!), I wandered over to Crown Fountain, a unique water feature flanked by two huge (50 foot tall) displays of matching faces.  I thought they were static images at first and then, to my surprise, they moved.  They blinked and smiled and after watching them carefully I could see all the tiny nuances of human expressions and facial muscle movements as well.  It was fascinating (and a little… creepy?) – I was completely transfixed.

After about five minutes they opened their mouths, pursed their lips and water came spouting out before the face gradually morphed and transformed into a different person.  It’s an incredible piece of digital art and well worth stopping by to watch for a while.

One half of Crown Fountain

After Crown Fountain I made my way to Cloud Gate, also affectionately known as ‘The Bean’.  I’m so glad I got there early in the morning – there were hardly any people there at all so I could get some good photos without the crowds.  It’s a shame it was cloudy, I image catching a colourful sunrise or spectacular sunset there would be pretty special to see.

It was very cool being able to see the city from so many different angles (quite literally!) in all the reflections of Cloud Gate.  It’s huge (much bigger than I thought it was going to be) and you can walk through the arch in the centre of it too – it’s pretty trippy if you look straight upwards when you’re directly underneath it. I felt like I was in the middle of a kaleidoscope.

Before my visit I didn’t think I was going to be very impressed or that it was going to live up to what everyone had been saying about it – I mostly went just to tick it off my list of ‘Things To Do In Chicago’ – and it ended up massively exceeding my expectations. A must-do (but go early in the morning!).

Cloud Gate, aka ‘The Bean’

Hi, it’s me!

I loved seeing the different reflections on each side of The Bean

By then it was time to head back to the hotel for the opening events of ClickAway – a networking breakfast followed by the keynote speaker, Lindsay Adler, who was fab.  She’s an award-winning fashion and beauty photographer, so not really my genre of photography at all, but her talk was all about ‘The Journey From Good To Great’ and it was inspiring learning all about where she’s started out and how she’s got to where she is today – I ended up taking three pages of notes!

At lunchtime I snuck out for a wander along Chicago Riverwalk, a 1 and a 1/2 mile long pedestrianised walkway that runs along both banks of the Chicago River through the city all the way to the edge of Lake Michigan.  It’s lined with bars and restaurants, green spaces and launch areas for kayaking and river cruises.  Every time I went there it was buzzing with energy and full of activity, whilst simultaneously being a relatively peaceful and relaxing place to escape to from the busy city sidewalks, rumbling L-trains and honking traffic.  And yes, the water really is that colour!

One of the entrances to the Chicago Riverwalk – a spiral staircase!

Chicago Riverwalk lined with rivercruise boats and flanked by imposing skyscrapers.

Chicago Riverwalk near Lake Michigan

After my stroll I headed back to the hotel for my first two ClickAway classes, both of which were awesome.   Meg Loeks (who I have followed and admired for years) spoke about having an impactful social media presence whilst still remaining authentic and true to your ‘why’.  And Dana Leigh (who I adore and who’s class I took at ClickAway in Atlanta) taught a practical lesson on how to take captivating black and white portraits.

On my adventures earlier this morning I’d stumbled across the Jay Pritzker Pavillion and noticed that it was hosting an event called Grant Park Music Festival – a month long programme of classical concerts, one each evening and all totally free.  Tonight’s offering was ‘Lights On Broadway’ – a medley of songs from different Broadway shows, some of which I’d heard of and some of which I hadn’t.

After my classes were done for the day I headed down to the Pavillion.  I timed it perfectly, arriving just as the orchestra were beginning to warm up and people were starting to take their seats in front of the stage and set up picnic blankets on the grass a little further back.  I love hearing bands and musicians getting settled and into their rhythm for a concert, all the different instruments’ distinctive sounds blending together.

The architecture of the Pavillion itself was fascinating (it made me think of War Of The Worlds for some reason!), the lighting effects made it even more dramatically beautiful, and, when coupled with the juxtaposition of the green and open space of the park surrounded by towering skyscrapers of the city, it really was quite an incredible thing to experience.  I’ve been to concerts in many different venues and this one was totally unique.   I stayed for four or five songs (out of the 20 or so on the programme).  Some were purely instrumental and others had vocals performed by some fabulous singers.  I’m so glad I went – it really was a memorable experience that I’ll forever connect with my time in Chicago.

By then it was time for me to make my way back to the hotel to get ready for the ClickAway opening night party.  It had a ‘Written In The Stars’ theme, so glitter was required!

A free classical concert at the Jay Pritzker Pavillion in Millennium Park



One of the advantages of having a room on the 29th floor of a hotel is the outstanding sunrise and sunset view each morning and evening.  My heart will always belong out in nature for sure, but I do love watching a city wake up to face the day and then settle down to sleep again at night – it’s always pretty special, no matter where I happen to be in the world.  This morning was no different – a stunning start to the weekend.

Sunrise from my hotel room

I took an early morning, pre-class wander through the city streets.  First I stopped by the iconic Chicago Theatre before stumbling unexpectedly across Picasso’s ‘Untitled’ (yes, a real sculpture by Picasso just right there in the middle of a square that I happened upon by chance!).

Next I discovered an incredible street art mural on back of the Chicago Cultural Center before turning my attention to hunting for the infamous Route 66 sign that signifies the very beginning of the classic journey from Chicago to Los Angeles via eight different US states.  Eventually I spotted it – it’s tiny and nondescript, perched inconspicuously above some traffic lights at a busy intersection just opposite the Art Institute of Chicago.  I’m so pleased I found it!  It’s an American road trip I’d absolutely love to do one day.

The iconic Chicago Theatre

Picasso’s ‘Untitled’ sculpture – it was huge!

Amazing mural on the back of the Chicago Cultural Center – I loved the colours and the detail

The sign indicating the start of Route 66, the classic American road trip

I lost track of time a bit whilst I was exploring, which I have a tendency to do when I’m somehere new.  I get so caught up in trying to capture the details and the bigger picture of all the cool things I see.  I ended up having to race back to the hotel for my morning class and made it just in time.  This one was photographing a gorgeous family alongside Natalie Gildersleeve, who I have wanted to meet and learn from for the longest time.

Because I only had the one class scheduled for today, with all afternoon and evening free for adventures, I’d planned and pre-booked something really quite exciting to do: SkyDeck Chicago.

SkyDeck Chicago is situated right at the very top of the Willis Tower (which used to be called the Sears Tower), formerly the tallest building in the world.  It cost me $37 (booked in advance online) and it was worth every single cent – this was definitely one of my most memorable moments from my trip.

There is an excellent and informative interactive exhibition at the beginning on the ground floor, which eventually leads you around to the lift that then whisks you up all 103 floors of the building in less than sixty seconds.  I went through the exhibition quite quickly but you could easily spend up to an hour wandering through if you stopped to read and look at everything – it was very interesting.

Once at the top you can walk around the whole floor for 360 degree views of the city.  I was lucky enough to have clear blue skies on this particular day so the visibility was fantastic and Chicago looked gorgeous as it basked contentedly in the summer sunshine.  On a really good day you can see four different US states – Illinois, Indiana, Michigan and Wisconsin – which I think is pretty cool.  I spent some time there taking it all in and then moved around to the next section where I queued for The Ledge.

The Ledge is actually four separate enclosed glass balconies that jut out from the edge of the skyscraper, essentially suspending you over the city with nothing but an inch and a half of toughened glass between you and the ground 1,353 feet below.  I waited for about an hour in total and it was totally worth it, even though you only get a short amount of time in the box (one minute for 1-2 people, two minutes for 3+ people and they’re really quite strict about it).  It’s just enough time to take some photos and enjoy the view.

Walking along the river on my way to SkyDeck Chicago

In ‘The Ledge’, looking directly down through the glass floor at the city bustling busily below me

The views from SkyDeck Chicago were incredible. This one, looking out over Lake Michigan, was one of my favourites.  The green area jutting out into the lake is Northerly Island.

Me in The Ledge!

I spotted this sculpture, called ‘The Flamingo’, on my walk back to my hotel after my SkyDeck Chicago experience. It made me think of the MindFlayer from Stranger Things!

After a bit of downtime relaxing in my hotel room I met up with two friends and we made our way over to Navy Pier for the evening.  One of the ‘must-do’s’ on my list for Chicago was to try one of the city’s famous pizzas, so that was our mission for the night.  We headed straight to Giordano’s, which is universally deemed to be the best place to get real Chicago deep dish pizza pie in the city.  We queued up to book a table and pre-order our food and were told that we’d get a text when our table was ready in about an hour’s time – that’s how popular they are!

Whilst we were waiting for the text to arrive we took the opportunity to wander down the length of the pier and back.  We people-watched, admired the boats and watched the sun beginning to set behind the city skyline.  Once our table was ready we then waited another an hour for the food to be delivered and it was 100% worth the wait.

We’d ordered a house salad and some mozzarella triangles to share as a starter and I could honestly have eaten the whole plate of mozzarella to myself – they were SO good.  We’d chosen ‘The Chicago’ pizza because it seemed fitting to be traditional.  It had pepperoni, green peppers and mushrooms on the bottom.  Then a layer of the stretchiest cheese I’ve ever had.  Then a layer of tomato sauce.  All baked in a crust that was more like shortcrust pastry than the pizza dough we’re used to over here in the UK.  I’ve never had anything like it before and it was honestly just so delicious.  10/10 would recommend.  It was an evening of great conversation and excellent company – I haven’t had so much fun in ages.  We shared stories, laughed and cried together, the best kind of way to bond over a meal.

The famous Chicago deep dish pizza pie from Giordano’s at Navy Pier

After dinner we had another wander along the pier, continuing our conversation whilst enjoying seeing the city lit up in the darkness.  The neon lights of the Centennial Ferris Wheel and the carousel illuminated the pier itself, which was still bustling with energy and excitement from people of all ages from tiny kids right the way up to elderly couples.

We stayed to watch the fireworks display (it’s only on certain days and we happened to be in the right place at the right time on the right day!).  It was only about ten minutes long but fireworks are my favourite so it didn’t matter at all that it was only short – I loved every second of the display, I’m like a big kid when it comes to fireworks.

Inside Navy Pier, which was full of shops and restaurants and all sorts of cool and interesting things. The architecture was amazing! I could have wandered around in there for ages.

Navy Pier is a gorgeous place to explore outside as well

Watching the sun beginning to set whilst we were waiting for our table at Giordano’s

The city skyline at night – so pretty!

The fireworks display was fun to watch, and a perfect way to end the evening.

As you can see, I squeezed a lot of fun, exploration and adventure into just two days and still had two more days of discovering the city to go!  Part Two of this blog post sharing my time in Chicago will follow shortly – hopefully within the next few days.

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1 Comment

  • Reply July 18, 2023

    Chicago attractions

    Awesome images from Chicago, especially the one with the sunrise. This city is one of the friendliest with visitors, and here are some awesome museums.

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