One thing that we don’t shy away from is enjoying some good drinks. Of course, we are all for drinking responsibly but when a couple reaches out to have their engagement photos at a bar… how could we resist! Keep scrolling to read more about these Chicago Engagement Photos at Bar Siena.

Whenever we’re working with our couples for their engagement session, we also strive to choose somewhere meaningful to them. This could be somewhere they frequently visit, where they got engaged or in this case where you had your first date! Kendall and Edward met up for drinks and had their very first date at Bar Siena here in Chicago! It was on that date that Kendall knew that he was the one for her and well… you know how the rest goes.

Chicago Engagement at Bar Siena

We met up with Kendall and Edward outside of Bar Siena. Naturally, we had to immediately get them some drinks in their hands. I mean it is called BAR Siena, right? While Bar Siena may sound like your run-of-the-mill Italian restaurant, trust us when we say it’s SO much more than that. The interior design of this location is truly one of a kind and really stands out. The moody and edgy vibe that Bar Siena gives off was right up our alley and we were LIVING for it. To read more about how Bar Siena came to be, click here!

We spent the remainder of our time at Bar Siena enjoying some incredibly delicious cocktails, soaking up the sun, and making sure our cheeks weren’t falling off from laughing/smiling so much. We even were able to sneak off for a quick milkshake break. Shh… don’t tell anyone though. Before we knew it, it was time to head to our next stop on this engagement adventure.

Engagement Adventures at the Alfred Caldwell Lily Pool

The excitement didn’t stop there though! We made a quick put stop at the Alfred Caldwell Lily Pool located inside the Lincoln Park Conservatory. The ACLP is the perfect oasis and get away from the hustle & bustle of Chicago. For any of you nature lovers out there, it is one of the most perfect locations for engagement photos – trust! Oh and surprise, did we mention that we did an outfit change? Kendall wore this deep v line blue dress while Edward spiffed up his look with a classic button-up. Both of them looked TO DIE FOR and to be honest… we’re fangirling over here. Don’t believe us though? Check it out for yourself!

Evening Walks at North Ave Beach

Oh and guess what… the celebration did not stop there! Are we giving you whiplash yet? We made the short commute over to one of our FAVE location spots, North Ave Beach! If you’re looking for that perfect mix of water & city views, then North Ave Beach is the perfect spot for you. Kendall changed into her final outfit, wearing this beautiful emerald green dress. Brb crying! Now trust us when we say we put in our 1000% when it comes to our couples. If that means we have to dig our toes, hell, even our whole bodies in the sand to get the perfect shot… well we will do it!

We finished off the night with of course some celebratory champagne pops, smooches by the water, and of course… donuts from BomboBar! It was the perfect way to end their engagement session and 10/10 would definitely do it again. So while you’re off enjoying more of Kendall and Edward’s engagement, we’ll be out here ordering about 12 boxes of donuts – ttyl!

Tip: Bring two bottles of (inexpensive) champagne to your engagement session. We are spraying it around and don’t want to be wasting the good stuff!

Oh and if you loved seeing all these Chicago Engagement Photos at Bar Siena, then you’re going to love these Ice Cream Engagement Photos at The Plush Horse.