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

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 started).

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.

You can read about the adventures I had during the first two days of my trip in this blog post here:  Four Days In Chicago: A Whirlwind Trip to the Windy City (Part One)

This post you’re reading now covers everything I did during the second half of my four days in Chicago.  Here’s what I got up to…



I was wide awake bright and early again despite having such a busy day and a late night out with friends at Navy Pier last night.  Thanks jet lag – I always seem to start adjusting to the new time zone just as it’s time to head home again!  It was a stunning morning so I headed out for a walk in the sunshine for some fresh air in search of what is allegedly the world’s largest Starbucks.

Ella discovered it in a reel on Instagram and shared it with me (“You HAVE to go and see it Mum!”) so, mission in mind, that’s what I did.  The Starbucks Reserve Roastery was easy enough to find and it really was huge: four stories tall and taking up a quarter of the block it’s situated on.  What really gave it away was the enormous queue forming outside the front door (it wasn’t open yet) that wrapped around the corner and trailed down the street.

I would have loved to have gone in as it looked absolutely beautiful inside – very aesthetically pleasing – but I had to get back for my morning ClickAway class.  Next time I’m in Chicago (and there will most definitely be a next time), I’ll go in for a drink and a muffin for sure.

Early morning sunshine in the city

The view downriver towards Lake Michigan from one of the bridges that spans the water

Every time I visit the US I’m surprised by the number of American flags I see flying everywhere but it’s actually one of the things I really love taking photos of.

Starbucks Reserve Roastery – allegedly the largest Starbucks in the world?  This was just the corner – it went back along half the block on each side of this curved part.

My final two classes of ClickAway photography conference were perhaps the two I was most looking forward to: ‘Creatively Capturing Children’ with Ashley Marston and a self portrait class with LeAnna Azzolini.

I learned some really cool, new-to-me techniques with Ashley.  I took her class at ClickAway Atlanta too – she knows her stuff inside out and is just so much fun to hang out with and learn from.  I love her.

I’ve adored LeAnna for such a long time – her honesty, authenticity and positivity is always so uplifting.  She also hosts an excellent podcast called ‘Curating the Curious‘ and has interviewed some awesome guests on that (you can find it in all the usual places – Spotify, Apple etc).  Getting to meet LeAnna in person after so long talking with each other online was ace – it felt like catching up with an old friend.  Self portraits have become a kind of therapy for me over the last nine months so I knew it was a class I wouldn’t want to miss.

Classes finished, and feeling a little sad that ClickAway was over for another year, I then had the rest of the afternoon and evening to explore some more and make the most of the final part of my four days in Chicago.

Street art murals like this were dotted all over the city – this was one of my favourites that I found along the Lakefront Trail.

I decided to get out of the city centre and head north, aiming to make it to Lincoln Park and North Avenue Beach Pier.

I’d heard lots of good things about Lincoln Park: a nature boardwalk, a zoo (free admission), a conservatory, plus lots of green space to wander through.  It’s also home to North Avenue Beach Pier, which is supposed to have fantastic views of the city skyline and is a ‘must-do’ if you only have four days in Chicago.

Ideally I’d have been there at sunset but as it was the height of summer it would have meant making my way back to my hotel in the dark really late at night, which I figured probably wasn’t all that sensible.  Instead, I set out late afternoon – it was still 31 degrees Celcius and there was zero shade as I walked along the Lakefront Trail.  Lakefront Trail is a pedestrianised walkway (which also doubles up as a cycle path) that runs parallel to Lake Shore Drive, one of the main highways through Chicago.   It hugs the shoreline of Lake Michigan and looks like it would be a spectacular route to drive.

I began my on-foot expedition at Ohio Street Beach, right next to Navy Pier.  It was an interesting juxtaposition – the vast expanse of water on one side of me, whilst on the other side were towering skyscrapers stretching upwards.  I walked for about 45 minutes, people-watching as I went, eventually reaching Oak Street Beach quite a bit sweatier than when I started out.  The section of the lake between these two beaches is known as The Playpen – it’s inside a breakwater which protects it from large waves, meaning that it’s safe to swim. It’s also the place to be ‘seen’ – party boats often congregate here.

At this point I’d run out of drinking water too, so I reluctantly turned around and retraced my steps.  I was a little disappointed to have not quite made it all the way to Lincoln Park but it just gives me yet another reason to return to this beautiful city one day.

Walking along the Lakefront Trail, heading north.

Oak Street Beach

I’d planned to spend the evening in my hotel room, relaxing and preparing for my journey back to England the next day.  The sky, however, had other ideas, putting on a rather spectacular display which quickly lured me out again, camera in hand.

I made my way down Chicago Riverwalk toward the lakeside, underneath ‘Stranger Things’ skies looming ever more ominously above me.  The colours evolved as I walked, lighting up the city skyline, the boats in the marina and Navy Pier with the most intense colours.  These photos don’t do it justice – it was incredible to see in person.  A perfect way to spend the final night of my four days in Chicago.

The marina at sunset

A ‘Stranger Things’ sky over the city

Navy Pier at sunset. I think this might be one of my favourite photos from my time in Chicago



My final morning of my four days in Chicago dawned with yet another stunning sunrise over the skyline.  I was awake early again, giving me plenty of time to explore one last area of the city before checking out of my hotel and heading to the airport in the afternoon for my overnight flight back to the UK.

Sunrise on my final morning in Chicago

This time I headed south along the Lakefront Trail, aiming to make it all the way to Northerly Island.  I didn’t quite get there, only making it as far as the Adler Planetarium.  I’m an avid walker and even so, I seem to underestimate every single time just how far away some of the things I want to see are, particularly on foot.  Time constraints are also a factor – you definitely need more than four days in Chicago if you want to be able to see all the things there are to see!

It was a really lovely walk.  I was out just after sunrise so there weren’t too many people around, the sky was still putting on a show, the water was gently lapping and it felt really peaceful as I wandered along, stopping for photos every so often.

Boats bobbing peacefully on the water along the Lakefront Trail

Dramatic post-sunrise skies at the Adler Planetarium

I love finding little things like this whilst I’m out exploring. And the view back towards the city skyline was fantastic.

These three little hearts painted on the path were cute too.

These footprints fascinated me. It was as if someone had walked through some spilled blue paint and then simply walked off the edge of the path into the water. I’d love to know the story behind them and what actually happened.

I took a slightly different route on my way back to my hotel, just a little bit inland from the water’s edge.  The path took me through a mix of landscaped and wild areas and I was absolutely thrilled to notice a monarch butterfly fluttering around.

I followed it (life motto: always follow the butterfly) and to my delight there were several more concentrated in one small area.  I’ve never, ever seen a monarch butterfly in the wild before so it felt like a pretty magical moment that tied together several threads of conversations I’d had with various people over the course of ClickAway – with LeAnna Azzolini in particular.

The perfect ending to a fantastic four days in Chicago.

A monarch butterfly in the wild

Adventures over, I returned to my hotel, finished packing up all my stuff, checked out and made my way to the airport for my long journey home.  I can honestly say that I had the best four days in Chicago and there is absolutely no doubt in my mind that I’ll return there one day – there’s so much more I want to explore!

O’Hare International Airport

Sunrise from the aeroplane on my way home to England after an incredible four days in Chicago



I loved every second of my time in the Windy City and let me just say that four days in Chicago is nowhere near enough to see and do all the awesome stuff that there is on offer.  Here are some of the other things I had on my list that I didn’t quite get round to.

I think a return visit is definitely in store, with the rest of the family this time as there’s SO much to do for kids and teens there as well.  I know they’d love it there.

If you’ve ever been to Chicago, what else would you add to the list of ‘must-do’s?  And if you’ve never visited before, which attraction would be top of your list to see?

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