Chicago 2017

August 6, 2017 - Chicago, Illinois

Europe left us with a serious case of wanderlust.

Every single day Kaila & I would be chatting with each other about groupon deals, Travelzoo specials… and just about any “sale” we would see on Expedia and the like.

I had an engagement shoot this past weekend in London, Ontario… and somehow, Kaila managed to get the weekend off as well.

Before we knew it, we were crossing the border and on the late night drive to Chicago, Illinois.


Kaila was cold in the windy city, so a sweater was necessary… and what better way to rep Chitown than with some wearable memorabilia?


Chicago was a place that both of us have wanted to visit for a while. It seemed suitable that after the shoot I had in London that we would keep driving. 8 hours from London, Ontario seems like a far drive, but we didn’t really care. We were looking forward to experiences like this in Chicago.

Neither of us had ever been to Chicago, so the experience was pretty neat. It was a little odd to me that while most cities would leave the river’s borders untouched with public parks and open greenery, Chicago built these monoliths right to the river’s edge.

It was quite a sight to see - after having driven through Toronto yesterday & seeing the skyline with the CN tower, I was blown away at how many more of those monoliths exist in the core of the city.


While I don’t at all condone graffiti, I love little spots like this (found in a stairwell descending from a bridge over the Chicago river).

These little murals are an offbeat insight into a small pixel of Chicago’s silhouette.

I’m so glad we managed to drive all the way to our hotel in Chicago instead of stopping somewhere in Indiana last night. Instead of waking up to a short hour drive, we woke up in the city with a 15$ uber downtown to explore. Much less stress.

We enjoyed a leisurely stroll along the promenade parallel to the Chicago river before making our way to Millennium Park to be tourists around the bean.


One of my favourite things to do when I’m in a new city is park the car and spend the day exploring on foot.

Thankfully, we had the hotel for two nights so we parked in their lot and Ubered into town.

We had been walking all day - Kaila bought a sweater (it was the windy city, after all) and we loaded up our backpack with water bottles - it truly was a beautiful adventure.

Also, Kaila never takes a bad photo. She makes it easy.

I’m incredibly thankful that I’ve had so many opportunities to travel with Kaila. We’ve had some absolutely incredible adventures together, and I’m so so glad that we both have such a wonderful time exploring the world together.

She’s getting more and more used to being in front of a camera (she’d better get used to it) but she still has moments like this when asked “ok ok time for a serious one”

The view from under the 'bean'

The view from under the 'bean'

Kaila and I accidentally stumbled upon this wet promenade… and it totally caught us off guard.

Apparently you can get your face up there (not sure how or where) and it cycles through.

The odd part of the whole experience was when the person behind the face would open their mouth and a jet of water would blast the kids eagerly awaiting the waterworks.

Not sure the metaphor but I appreciate the art (at face value).


We didn’t know at first, but apparently this weekend was Lollapalooza - so we were dealing with hoards of drunk people day and night. It was kinda like an episode of Walking Dead.

From Millennium Park, we rented some bikes and made our way toward the Navy Pier. Through the mall we made it to the Crystal Gardens where we took a quick break around the fountains.

This trip was super impulsive (Kaila managed to get three days off in a row somehow) but in a way, it was a little celebration for our two year anniversary.

I’m so happy and thankful to have the best travel buddy of all time - we really do have some of the best adventures.


I love when cities respect their elders like this.

I see it more-so in Europe, but it’s pleasant to see in North America as well.

Surrounded by corporate monoliths is a vine-covered cathedral in the heart of downtown Chicago.

After a full day of exploring around downtown Chicago, we made our way back to our hotel to get ready for dinner. We ubered back and after a delicious southern meal at Banderas with some live jazz, we took a quick stroll around the city to get a few views of the skyscrapers at night.

I was extremely thankful that we actually decided to make the road trip here - it was a lot of driving for just one full day in the city, but it was totally worth it.

Though this trip came to an end, we were excited about the prospects of future travels. We were so glad we made it and explored the city for the weekend.

We’ll certainly be back at some point!