Surprise Proposal in Chicago’s West Loop| Ally and Connor

Connor and Ally have a deep connection to the city of Chicago, so when Connor reached out to me about proposing while he and Ally were visiting I was beyond excited! Chicago is an incredible city with SO many different locations and neighborhoods that make it the one of a kind place that it is. One such Chicago neighborhood is the lovely West Loop which is where Connor and Ally’s proposal took place!

Proposal in Chicago’s West Loop

One of my talents as a local photographer in Chicago is my knowledge of the city which lets me pick out the perfect location for a proposal for those that may not know all the nooks and crannies of the Windy City! For Connor’s proposal to Ally that perfect spot would be in front of Trivoli Tavern, a restaurant in Chicago’s West Loop that has the most GORGEOUS front patio. With string lights overhead and brick walls surrounding them, Connor popped the question to Ally to which she excitedly said yes to! The moment was so sweet and special, Ally even teared up a bit while overcome with joy. We then headed off to The Bandit for a quick drink where Ally and Connor were treated with a round of shots with sparklers attached to them to celebrate!

A Night of Celebration

After our pit stop at The Bandit, Ally, Connor, and I headed back out into the streets of Chicago’s West Loop for some more portraits to celebrate their proposal! Connor had a surprise lined up for Ally later in the evening, but we had time to burn until then. This let us explore one of the coolest seasonal pop ups of Chicago, the Jack Frost Market! We were able to capture some incredibly fun portraits taking advantage of the holiday lights of the market. From there we then made our way to Boqueira West Loop where Connor had arranged for ALL of their favorite people to gather to surprise Ally! Safe to say they pulled it off, and it was the perfect end to a magical evening!

Even though Ally and Connor had a rainy evening for their proposal in Chicago’s West Loop, that didn’t stop them from having the night of their lives! I’m overjoyed to have been a part of these two’s proposal, and to have captured all of the emotions they felt from such a wonderful evening! Check out my blog if you’re looking to read about more love stories like Ally and Connors. Looking to book me for your own proposal or wedding day? Head to my contact page to send an inquiry my way!