Classy Engagement Photos in Downtown Chicago | Alysa + Adam

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2 photos side by side of a couple standing in a street of Chicago with buildings all around them, in the left photo they are smiling and in the right they are kissing

I had the absolute pleasure of capturing my FIRST EVER engagement photos in downtown Chicago last month! First off, thank you to my Chicago photog friends for helping me with the parking, planning, and more. Second, a HUGE congratulations to Alysa and Adam on their engagement and their incredible session! These two have a magical story and such a purposeful engagement session that I am so excited to share with you all!

A man and woman smile at one another before kissing while standing in a street of Chicago surrounded by buildings as they take their engagement photos

Getting to Know Alysa and Adam

Before we really dive into Alysa and Adam’s engagement photos from downtown Chicago, let’s take a quick trip to the past to see how we ended up here. The two met at Millikin University in Decatur, IL where Alysa played softball and Adam played baseball. After a constant crossing of paths, and their friends setting them up, the two finally began dating in 2018 and have been together ever since!

They got engaged in Traverse City where they travel to once a year, and chose Chicago for their engagement session and wedding as the city holds a special place in their heart. It’s where Alysa grew up, where Adam went to law school, and where Adam realized that Alysa was the one he’d marry. While Adam was in law school Alysa would visit, and when it came time for her to head back to central Illinois things just felt empty for Adam. This realization is what led to the proposal and finally what led to their spectacular engagement session!

Black and white engagement photo of a couple walking across a street of Chicago together and smiling while holding hands
Engagement photo of a couple walking across a street of Chicago together and smiling while holding hands
2 photos side by side of a man hugging a woman and kissing her on the neck while she smiles as they stand on a street of Chicago

Their Engagement Session in Downtown Chicago

Alysa and Adam are having their wedding in Chicago in October of 2024, the theme of which is going to be black tie formal. Wanting to be consistent with the feel and style of their wedding, the two chose to have the same classy style for their engagement photos in downtown Chicago. Talk about stunning! These two were simply gorgeous, and combined with the architecture of the Chicago Board of Trade Building they looked like something straight out of a movie. Of course we couldn’t have their engagement session in the city without making a stop at North Avenue Beach for some portraits with a gorgeous Chicago skyline! 

A man and woman walk hand in hand towards the camera and smile at one another while taking engagement photos, they're walking towards the camera down the middle of a street in Chicago
Black and white engagement photo of a couple walking hand in hand towards the camera while in the middle of a street in Chicago
2 photos side by side, the left is black and white of a couple smiling while crossing a street of Chicago together, the right is of the couple dancing in the street together
2 photos side by side, the left is black and white of a couple smiling while standing on a street of Chicago, the right is of the couple standing in front of a gold doorway
Close up photo of a woman's hand with an engagement ring resting on the chest of a man during their engagement session in Chicago
2 photos side by side, the left is of 2 hands reaching out to one another in front of a gold doorway and the woman's hand has an engagement ring on it, the right is of a couple about to kiss while skyscrapers loom above them
Black and white photo of a man buttoning up his suitcoat
2 photos side by side of a woman, in the left she is smiling at the camera while standing in front of a gold door, in the right she is facing away from the camera and adjusting her hair while showing off the engagement ring on her finger
A couple smiles while touching foreheads together as they stand on a street of Chicago while taking engagement photos
Black and white photo of a couple smiling while touching foreheads together as they stand on a street of Chicago while taking engagement photos
Black and white photo of a couple kissing one another while taking engagement photos on the streets of Chicago
2 photos side by side, the left is of a couple standing next to one another in front of a large gold door, the right is of them standing side by side next to a huge marble pillar
2 photos side by side of a couple standing next to a massive marble pillar, the left photo is of them kissing and the right is black and white and is of them looking to the left
Black and white engagement photo of a couple embracing one another while in Chicago, the man is looking at the camera while the woman has her eyes closed
Black and white engagement photo of a couple standing in Chicago and smiling at the camera as it moves towards them
Black and white engagement photo of a couple standing at North Avenue Beach with the Chicago skyline in the background, the man is looking at the woman while she looks back at the camera
Engagement photo of a couple standing at North Avenue Beach with the Chicago skyline in the background, the man is looking at the woman while she looks back at the camera
2 photos side by side, the left is of a couple kissing with skyscrapers behind them, the right is of the couple smiling at one another with the Chicago skyline in the distance in the background
A couple lean in to kiss one another while taking engagement photos at North Avenue Beach, in the background is Lake Michigan and the Chicago skyline
Black and white photo of a couple leaning in to kiss one another while taking engagement photos at North Avenue Beach, in the background is Lake Michigan and the Chicago skyline
2 photos side by side of a couple, the left is black and white and is of them holding hands, the right is in color and is of them smiling at the camera while standing in front of lake Michigan and the Chicago skyline
Photo of a couple standing at North Avenue Beach together and smiling at the camera while the woman shows off her engagement ring with Lake Michigan and the Chicago skyline in the background
2 photos side by side of a couple standing at North Avenue Beach looking at one another with Lake Michigan and the Chicago skyline behind them, the left is in color while the right is in black and white
2 photos side by side of a couple, in the left photo the man is hugging the woman from behind as they kiss, in the right photo they're in the same position and smiling at one another

I honestly couldn’t be happier with how my first engagement session in Chicago went and how Alysa and Adam’s photos turned out! I had SO much fun with these two, their October wedding can’t come soon enough! For more love stories like theirs, or wedding planning tips, be sure to check out my blog. Ready to book me for your wedding day and engagement session? Head to my contact page to send me an inquiry!

Photo of a couple kissing, the man is standing behind the woman as she holds his hand showing off her engagement ring, behind them is Lake Michigan and the Chicago skyline

Engagements

November 23, 2023

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