Syd & the City Photography LLC

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Chicago, IL
Syd & the City Photography LLC

Welcome, happy you’re here! My name is Sydney and I am a Chicago-based photographer specialized in engagement and wedding photography! Inquire at my website.
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08/16/2026

A favorite session of mine that I never got to sharing? This one! A year ago we took these announcement photos on a relaxed sun filled Sunday. L + J’s baby arrived before this insta post!

I love photos that accurately capture the energy of the couple and these do just that. It was such a joyful time strolling the harbor together and their dog, Phoenix loved the camera!☀️

I’ve been mia on Instagram as I’ve enjoyed my own summer (including the crazy Chicago weather that I’ll be requesting a redo on), but I look forward to sharing more from this year’s weddings and projects soon before the hecticness of the fall arrives❤️

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Chicago wedding photographer, Chicago engagement photographer, announcement photos

07/21/2026

A little of what I’ve been up to lately! I’ve been working hard editing and can’t wait to get more galleries out soon 🤍

1. M + E’s backyard wedding - loved the embracing of warm summer colors and it felt like sunshine in the form of a wedding! They are such thoughtful and fun individuals🧡

A + T’s riverwalk and Art Institute engagement session - loved their fun and upbeat personalities and getting to photograph them around the art they love (now they’re the art)!

T + R’s Mexico wedding - loved getting to photograph this caring couple in a sunny and vibrant beach setting. It feels like forever ago we were in a dive bar taking engagement photos. They nailed it with the details and this was a change of pace from my usual Chicago work!

K + K’s Mom’s Place engagement session - loved getting to meet one of my sweet 2027 wedding couples! They had their first date here and I’m all for a fun nostalgic photoshoot. Can’t wait for the wedding!🎱

L + T’s City Hall Elopment and boat adventure - loved getting to photograph this down to earth couple and their loved ones at City Hall! We bopped around to the Cultural Center and down to the riverwalk to catch a retro boat, such a great day⚓️

C + B’s Chicago wedding - loved that this couple was down for all the photos and are such fun-loving people! Grateful for being a part of documenting their day and witnessing their complete trust in me. Also, go ILLINI!🤍

J + M’s riverwalk engagment session - loved getting to meet another one of my lovely wedding couples! They committed to the vision and were such a joy to hang around that time flew. Can’t wait to see you both again in September 🤍

A + J’s Alfred Caldwell Lilypool proposal - loved being a witness to this exciting next step in their relationship! Even more special as I photographed them before at another one of my couple’s wedding. J was so thoughtful with his propose and managed to make it was a a total surprise to A. Their energy and excitement was contagious❤️

Can’t wait to share more soon!😊

-Chicago wedding photographer, Chicago engagement photographer, lifestyle photos

06/26/2026

This past weekend offered a beautiful reminder of exactly why I fell in love with what I do. There is no greater fulfillment than a couple who pours complete trust into the process. We started with the thought of a beautiful backyard barbecue that soon elevated into a breathtaking tented evening, anchored by a beautiful surprise nuptial that left every guest in awe. and have such grace and a genuine kindness about them, being part of their story is a gift I will always hold close.

This evening was a true collaboration, and I am grateful to the immense talent of the creative partners who worked alongside me to make it a reality.

style and planning |
photographer |
caterer |
florals | .florals
spritz cart |
custom paper goods |
bar |
signage |
welcome sign & flag |
cocktail music |
dj |
linens |

06/14/2026

Choosing a photographer is like picking a friend to travel with☀️

- I go with the flow, but I plan for what matters
- We’ll share some laughs together along the way - I’ll stay calm when things don’t go according to plan  - I’m supportive, adaptable, and always looking for ways to make the most of the experience

Whether we’re chasing sunsets in a new country or celebrating one of the biggest days of your life, my goal is the same: keep the vibes high, the stress low, and the memories unforgettable🤍
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My Lisbon & Madrid trip caught on digital, film, & iPhone🎞️

Chicago wedding photographer, engagement photography Chicago elopement photographer

05/11/2026

Happy Mother’s Day to all the wonderful moms out there!♥️

This Mother’s Day is extra special as my best friend from college has officially announced her pregnancy!! Getting to not only be a friend, but someone to document the milestones of my loved one’s lives means the world to me. We toured their cute new house, took some photos, and ended with grill cheese sandwiches and a yap session! Their future baby will be so well loved.

These capture the playful and caring nature of Molly and Zach. It feels like only yesterday we all were at U of I together🥹

I’m in awe of all those I know raising the next generation and living out their lives to the fullest! I personally can’t keep a plant alive so it may be a little while until I join the club (lol).

Hope you all had a peaceful day and felt loved!

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Chicago couples photographer, Chicago wedding photographer, pregnancy announcement images

03/02/2026

Tickled Pink💕

An evening filled with laughter, food, music, dancing, and PINK! Most importantly, fundraising to support Chicago Foundation for Women.

02/23/2026

Gabi & Karla’s City Hall Elopement🤍

On a sunny summer day surrounded by close loved ones, they got married at City Hall and a photo session at The Art Institute followed! Karla and Gabi have such a calm and caring presence to them. Like friends you’ve known for a while, though to be fair, I had photographed them with their doodle Bailey a few times before this. Wrangling an energized dog for Santa photos together does build some level of trust lol. This allows their photos to look natural and highlight their love.

As always, I was grateful for them believing in me to document this special memory for them. It’s an honor. Congratulations to you both and many loving happy years to come!🤍

Chicago elopement photographer, Chicago wedding photographer, engagement photographer, art institute, city hall elopement

02/22/2026

It’s all in the details✨

02/13/2026

Love a venue with some personality! This wedding felt like it was straight out of a fairytale💕

One of my favorite things about wedding photography is getting to use my creativity to intertwine telling the story of your special day in a way that incorporates the uniqueness of the venue backdrop(s) you’ve chosen!

While a walkthrough beforehand is not always possible, I like to scope out the space upon arrival and get your input on what areas call to you. Sometimes the way the lighting hits a certain spot will guide us there too!

This wedding was second shot for the amazing . I’ll have to share a part 2 with the couples photos!

Chicago wedding photographer, Chicago weddings, engagement photographer, Chicago elopement photography

01/23/2026

The snow is kind of pretty when it’s not accompanied by below -0 windchill, am I right?

Lydia & Danny held an intimate New Year’s Day wedding in Central Park on top of a snowy rocky hill, perfectly connected to how they met — mountain climbing. Complete with matching bride and groom earmuffs🤍

I love when couples make their day uniquely theirs!

Stay warm,
Sydney

Chicago Wedding Photographer, New York City wedding photographer, engagement photographer, Central Park wedding photos

Address

Chicago, IL

Website

https://sydandthecityphotography.com/

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