Caitlin + Chris : Chicago Loop Engagement

When you get a sunny day in Chicago during the first weekend of Spring, you spend ALL afternoon out in it!  I could NOT be more excited to share this engagement session.  Caitlin & Chris are the last couple in an amazing group of friends, all of whom, I’ve had the honor of photographing.  These two are seriously two of the kindest souls you will meet.  And I’m lucky enough to call them my friends.

Ever since we started talking out where and when their engagement would be, they had been open to anything I suggested. And in true Caitlin and Chris kindness form, they made sure I was ok all afternoon…you know, the photographer in a winter coat and hat on a chilly day…while they didn’t even wear coats! Yep, makes sense. 😉

Pretty much, they are just the SWEETEST couple and I cannot WAIT until their wedding this Fall in Cincinnati.  How fun is it that they get pictures in two big cities?!

Up first, we start in Chicago by the iconic Chicago Theatre.

We took advantage of that bright sunlight all afternoon, especially because of the Chicago wind!

(I actually had some random person walking by – in a winter coat like me – ask if Caitlin knew it was March. Yes dude, but we are going to act like it’s August in Mexico so please keep walking.) 😉

That picture on the right? One of my all time favorites! And it was literally minutes after we started!

They made each other laugh and smile all day. I had a blast photographing these two! <3

Chris became a PRO at picking Caitlin up and spinning her around…keep scrolling.

And I was having a blast playing with the sunlight and shadows in the city. <3

I mean… <3 <3 <3

Caitlin, this is for sure another favorite. You are STUNNING!

Don’t get me started on that RING!

Our 2nd stop was Kinzie Street Bridge.

Hey, stand there in the middle of the bridge while the traffic goes by.

Ok, cool.


(Side note : does anyone see that sign in the background and what it says? ‘LIVE BRIGHTER‘ – Love that for this shoot!)

That SKY!!!! Seriously, the sun was awesome that day!

Ok, I have WAY too many favorites and that one on the right? We will add that into the list for sure! You two are adorable!!!

🙂 🙂 🙂

That SUN, that RING, this DAY! So PERFECT!

So…we were PLANNING on taking a cab up to Montrose Ave Beach for more city landscape shots but the universe (rather Chicago cabs) had other plans.  We were in a cab after the bridge and about to get on to Lake Shore Drive and BAM! He hit the median! We had to actually get out because his front tire was flat.  Luckily, we were all ok AND we were right in front of North Ave. Beach so easy going Caitlin and Chris decided, let’s just go here.


I think this spot was meant to be. So much fun!

(Don’t let those big smiles fool you….IT WAS FREEEEEEEEEZING!!!!)

You two are troopers!

Hug it out and keep each other warm!

Remember when I said Chris was a pro at picking up and spinning Caitlin?

Case in point : Left picture!


And then there is this…

They had planned to bring a bottle of their favorite champagne to pop at the end of their shoot.  Well, we had been walking around with it all afternoon and it was REALLY chilly.  So when Chris was about to pop it, I said to wait one second so I could back up and get the whole thing and….POP!!! LOL! I believe Chris’s face says it all.  (Also see Caitlin’s eyesight line.) HA!

So here’s an idea….let’s remake it?! #fakeittilyoumakeit??? LOL!

Because it wouldn’t exactly pop, Chris just threw it into the air making it even funnier.

HA! At this point, just pour the glasses and drink it up.

So funny and forever a great story!


Also, they are the sweetest, and brought an extra glass for me to toast with at the end of the session.

So much fun!  Check out our toasting boomerang on Instagram HERE.

Congrats you two! I had such a blast and LOVED every second of this crazy afternoon with you.

I seriously cannot wait for your wedding.  We are going to party all night! 😉


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