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

A man gets down on one knee to propose to a woman while outside of the Trivoli Tavern in Chicago
A man gets down on one knee to propose to a woman while outside of the Trivoli Tavern in Chicago

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!

A couple smiles while standing outside of the Trivoli Tavern in Chicago as the man puts an engagement ring on the woman's finger
A woman smiles as a man kisses her cheek while outside of Trivoli Tavern in Chicago after her proposed to her
A couple smile at the camera while outside the Trivoli Tavern in Chicago, the man raises his arm in the air as he just proposed to the woman next to him

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!

Close up photo of a woman's hand with an engagement ring on it and a man standing next to her, the photo was taken after their surprise proposal in Chicago's West Loop
A couple sit inside The Bandit in Chicago and smile at the camera while the woman shows off her engagement ring after their surprise proposal in West Loop
A couple smile at one another while sitting inside of The Bandit, the woman shows off her engagement ring to the camera after their surprise proposal in West Loop Chicago
A couple sitting inside of The Bandit in Chicago kiss one another while sitting at a table, the woman shows her engagement ring to the camera after their proposal in Chicago's West Loop
A couple sit in The Bandit of Chicago and have drinks with sparklers given to them as they celebrate their proposal in Chicago's West Loop
A couple sit at a table inside The Bandit and raise their glasses with their friends to celebrate their proposal in Chicago's West Loop

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!

A couple kiss one another while under a tunnel of lights in the Jack Frost Market to celebrate their proposal in Chicago's West Loop
A woman smiles at the camera while being kissed on the cheek by a man while under a tunnel of lights in the Jack Frost Market
A woman smiles at the camera while being kissed on the cheek by a man while under a tunnel of lights in the Jack Frost Market
A couple embrace and smile at one another while standing in front of a structure of birch trees and lights inside of the Jack Frost Market
A couple embrace and smile at one another while standing in front of a structure of birch trees and lights inside of the Jack Frost Market
A woman is hugged by her mother while inside a bar after she was proposed to in Chicago's West Loop
A woman and her friend facetime another friend on a phone while inside of a bar
A woman shows off her engagement ring to her mother while sipping champagne in a bar after she was proposed to.
A couple smile while standing next to some friends inside of a Chicago bar as they celebrate their proposal in the city's West Loop neighborhood
A man stands in-between a couple and kisses his friend on the cheek while the woman makes a funny face at the camera
A woman shows off her engagement ring to a woman who takes a picture on her phone while inside of a Chicago bar
Close up photo of a woman's hand that shows off her engagement ring as she holds a glass of champagne

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!

A couple stand next to one another while inside of a bar in Chicago and smile at the camera as the woman shows off her engagement ring
A woman smiles at the camera while being kissed by a man on the cheek inside of a bar in Chicago as the woman shows off her engagement ring to the camera

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