Humboldt Park Engagement Featuring Cocktails at California Clipper – Jessie & Rick

Fall has always been a popular time of year for engagement photos, and it’s still in full swing! One of my first sessions this season was with Jessie and Rick in Humboldt Park. Many of you know I call this neighborhood home, but it also happens to be where Jessie lived when she and Rick first got together! I was thrilled to take a trip down memory lane and visit some of their favorite local spots.

Chicago Cocktail Bar Engagement

I met these two at one of our mutual favorite spots, The California Clipper on a lovely October evening. If you’re in Chicago and have never been to the Clipper, I highly recommend checking this place out! Not only is this bar almost 100 years old, they also have live music most nights and a cocktail list worth sampling. But – I digress!

Jessie and Rick were as adorable as ever, and I was just a little bit obsessed with Jessie’s engagement ring (Rick designed it himself!). After a couple of mocktails and some stellar dance moves, it was time for a quick outfit change and stroll down California Avenue.

Humboldt Park Engagement Photos

One of my favorite things about this neighborhood is that it never gets boring. There’s a mix of buildings and businesses that have been in Humboldt Park for decades, but also new places popping up all the time. California Avenue is particularly photogenic – especially for street art! Of course we had to stop for photos with murals by local artists Sick Fisher and Jason Brammer. Finally, we arrived at Humboldt Park just in time for golden hour! Jessie and Rick were a breeze in front of the camera, and I could not be more excited for their wedding day next year 🙂

Jessie and Rick: Your Humboldt Park engagement session was a dream! Can’t wait to do it again next year!!

A couple announces their engagement outside The California Clipper, a classic cocktail bar, captured in black and white.
Engaged couple sits in a red booth at California Clipper
Couple sits at a red booth, holding hands beneath soft lighting and twinkling blue string lights at California Clipper in Humboldt Park Chicago
A couple sits in a dimly lit cocktail bar booth at California Clipper in Chicago, smiling and enjoying drinks together, celebrating their recent engagement.
Happy couple celebrates their engagement with a toast of champagne at California Clipper
Black and white photo of engaged couple sitting in a dimly lit booth, sipping drinks with a mountain mural in the background at California Clipper
Black and white photo of engaged couple sitting in a dimly lit booth, leaning close and enjoying drinks at California Clipper cocktail bar
Couple dancing in a dimly lit room near a neon
Couple embraces at the California Clipper cocktail bar, with a neon
Black and white photo of couple dancing happily in a dimly lit California Clipper cocktail bar in Chicago
Creative photo of woman standing while a man sits in a booth at the California Clipper cocktail bar
A woman stands with a cocktail in hand, while a man sits across from her in the dimly lit California Clipper cocktail bar with vibrant red decor and a glowing
A couple dances and kisses under a
Portrait of engaged couple sitting on bar stools with drinks surrounded by warm red lighting in the California Clipper cocktail bar in Chicago
Man and woman laugh while sitting on bar stools, drinks in hand, at the California Clipper cocktail bar in Chicago
Adorable cocktail bar engagement photo of man kissing woman on the cheek as they hold cocktails at California Clipper captured on 35mm film
Engaged couple's hands holding drinks at the California Clipper cocktail bar in Chicago
Black and white photo of engaged couple sitting at the bar in the California Clipper, smiling and holding drinks
Black and white photo of couple sharing a romantic moment in the California Clipper cocktail bar
Couple kisses in front of The California Clipper, a vintage cocktail bar in the Humboldt Park neighborhood of Chicago
Engaged couple poses in front of a colorful, abstract mural with swirling patterns and a triangular design in Humboldt Park, Chicago
Candid photo of couple in front of a colorful, intricate mural featuring patterns, stars, and geometric shapes in Chicago's Humboldt Park neighborhood
Man kisses his partner on the forehead in front of a colorful, abstract mural during their Humboldt Park Chicago engagement session
Black and white photo of couple smiling at each other in front of a mural with
Engaged couple poses in front of a brick wall mural depicting palm trees and mountains in the Humboldt Park neighborhood in Chicago
A couple stands in front of a mural with palm trees during their Humboldt Park engagement session
A couple holds hands in front of a mural depicting a scenic landscape and parked car during their engagement session in the Humboldt Park neighborhood of Chicago
Engaged couple holding hands in front of a mural featuring a car with a license plate reading
Creative Humboldt Park engagement photo with black and white Sick Fisher mural captured on 35mm film
Engaged couple stands holding hands in front of a brick wall with two windows during their Humboldt Park session
Couple embraces in a Humboldt Park's Formal Garden, surrounded by flowers and warm sunlight, during their engagement session
Engaged couple walks along a colorful garden path lined with red and purple flowers in Humboldt Park's Formal Garden
A couple walks and kisses in a garden surrounded by colorful flowers and greenery at sunset, capturing the timeless romance through film photography.
Couple strolls through the vibrant Formal Garden at sunset, surrounded by colorful flowers and trees during their Humboldt Park engagement session
A couple embraces in a field of tall grass, surrounded by greenery and a rustic wooden structure reminiscent of a cozy cocktail bar in the background.
Black and white photo of couple laughing and embracing in tall grass in the Humboldt Park Formal Garden
Romantic fall engagement photo in Humboldt Park Formal Garden with sunlight peeking through trees captured on 35mm film
Romantic fall engagement photo of couple at Humboldt Park lagoon captured on 35mm film
Fun engagement photo in Humboldt Park showing off engagement ring on rocks near lagoon captured on 35mm film
Happy couple stands by a pond as the woman shows off her ring during their Humboldt park engagement session
Engaged couple kisses next to a pond, surrounded by lush greenery and vibrant autumn foliage in Chicago's Humboldt Park
Black and white photo of woman displaying her engagement ring while she and her partner stand next to a pond in Humboldt Park
A couple dances by a pond surrounded by autumn trees and grass under a clear sky during their Humboldt Park engagement session
Black and white photo of engaged couple embracing on a path surrounded by tall grass and trees in Chicago's Humboldt Park

2 Replies to “Humboldt Park Engagement Featuring Cocktails at California Clipper – Jessie & Rick”

  1. Vanessa says:
    November 7, 2024 at 10:00 pm

    Stunning couple & stunning work!! Doesn’t get better than this!

    Reply
    1. Emma says:
      December 2, 2024 at 10:48 pm

      Thank you so much, Vanessa!! I could not be more excited for their wedding day!

      Reply

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