My Bucket List for Chicago Couples Sessions

Since I’ve moved to the Windy City, Chicago has quickly become my favorite city for my couples sessions! It’s really not a fair competition though as there is just SO much to love about this incredible city, and there are so many great options for where to have your session and what to do for it. That’s why today I want to take you through my top 5 bucket list locations for photography sessions in Chicago!

fiancé's look into each others eyes on a windy day in Chicago.  They are taking their engagement photos at North Avenue Beach.

Why Chicago for Your Photography Session

As I mentioned above, Chicago is an incredible city not just to live in but for any couples session. There are so many different settings and vibes that the city has to offer and so much to do all throughout the city that there’s really something here for everyone.

Limitless Settings

Chicago is an immensely diverse city with a ton of different neighborhoods and locations all with their own distinct feel to them. Whether you want the true downtown feel for your session, something where you’re surrounded by nature, or anything in between Chicago has you covered. The options don’t stop there though! If you know someone with a boat or want to rent one we can head out on the lake, we can rent out a hotel room or head to your apartment for an indoor session, or head into the city at night to get the Chicago lights in all their glory. There are SO many options for settings for your couples session in Chicago, but the fun doesn’t stop there!

There’s So Much To Do

Not only does Chicago have endless options for settings for your session, you can also do pretty much anything you want for your session to truly make it unique to you! Love vinyl? Head to your favorite record store and we’ll get some photos of you perusing their records! Are you both coffee fanatics? Let’s hit up one of the many incredible coffee shops throughout the city for a lovely start to your session. Do you both love the nightlife in the city? Let’s pop some champagne at your apartment before heading out and exploring the beauty of the city for your session. The possibilities are really endless! One thing to note if you do want to have your photography session at a location like a restaurant, bar, or something similar it’s best to call ahead to make sure they allow photography sessions to happen there. 

Perfect for Any Session

With the combination of settings and activities to do in Chicago, you really can create the couples session of your dreams. No matter what you’re looking for and what feel you want to capture in your photos, Chicago can provide! I love when my couples want to get creative with their session and make it truly unique to them as well, so if you have ideas for your session that you’re unsure on how to make work let’s plan it together. 

A future bride and groom walk past the Chicago skyline on the ribbon at North Avenue Beach.

My Bucket List for Chicago Couples Sessions

1. Sunrise at North Ave 

As I’ve mentioned before, North Avenue Beach is for sure one of my favorite spots in Chicago for photos, but having your photography session at sunrise simply cannot be beat! There are a few reasons that sunrise at North Avenue beach is a dream come true. First is the beauty that comes with a sunrise on the lakefront. With the sun rising over the lake and reflecting off the water and the windows of the buildings it creates such a magical feeling for your photos. Plus with how popular North Avenue Beach is from day to day a sunrise session is your best bet to have this Chicago beach to yourself for your couples session.

An engaged couple crosses the street at night in Gold Coast Chicago while smiling at each other and holding hands.

2. Nighttime Flash with Champagne Poppin’ 

Late night date night!!!!!!  Let’s pop by one of your favorite pizza or ramen spots and then pop some champagne because you live in one of the coolest cities in the world. Nighttime flash photos are some of the MOST fun photography sessions you can have, and what better city to have your session in than Chicago.  There are so many unique spaces that thrive in the nightlife of Chicago, and offer cool and unique backdrops for your couples session.  The Chicago Theater, the Crown Fountain, the River Walk and Michigan Avenue, all offer stunning backdrops with city lights for your session.

An engaged couple holds hands while walking next to each other down a sidewalk in Wicker Park Chicago

3. Snuggly In Home or Neighborhood Session

In-home sessions and neighborhood sessions are SO special! I love how many unique buildings and neighborhoods there are throughout this city and how each person makes their space their own! Let’s head out to your part of town and see all your favorite spots and take in all the beauty that made you both fall in love with where you live. Every neighborhood in Chicago has its own charm to it making them SO much fun for photography sessions. Then we can head back to your apartment for you two to cuddle up, put on your favorite vinyl and finish our session snuggling in the space you call home.

A newly engaged couple kisses while the fiancée sits on her fiancé's lap on a boat looking over Lake Michigan and the Chicago Skyline.
A close up image of an engaged couple pouring champagne into plastic couples while celebrating their engagement on a boat on Lake Michigan in front of the Chicago skyline

4. River Boat Session

Yes, the city of Chicago is beautiful from the streets, but let me tell you, seeing the city from the Chicago River or Lake Michigan is an EXPERIENCE.  Renting out a boat and touring the city for your sunset engagement session sounds like an absolute dream.  Pop some champagne, do a little dancing, have a picnic on the front of the boat and maybe even end your session with a swim!  If you don’t own a boat yourself or know anyone with a boat, you can rent a boat on the Chicago River or Lakefront for your session.

An engaged couple has fun inside a Chicago building during their engagement session.  They stand overlooking a banister almost kissing.
An engaged couple walks down the stairs looking at one another holding hands and smiling.  The wood stairs reflect the light from the flash.

5. Fancy Chicago Hotel for Couples Session

Chicago is home to some of the COOLEST architecture and interiors.  With some of the city’s most iconic buildings dating back to the early 1900s, there is so much history in Chicago’s architecture, making these locations some of the coolest spaces to have your engagement or couples photos.  Some specifics on the buildings on my bucket list include, The Palmer House Hotel, Gilt Bar, The Kennison in Hotel Lincoln, The Rookery Building and so many other cool spaces. Think nighttime flash photos mixed with the perfect amount of ornate interiors surrounding you and your lover.

I’m so glad that I get to live in Chicago for a variety of reasons, but the main one is I get to photograph so many different and unique sessions throughout this incredible city! If you have a session you’ve been dying to set up, or if you like the sound of one of my bucket list sessions I’d love to photograph it! Head to my contact page to send me an inquiry so we can start planning ASAP!

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About Jayde 

Docu-torial Photographer

I'm a Chicago wedding photographer with a passion for people, candid moments, authenticity, and golden hour. I document weddings with a ferocity for the real moments that matter on a wedding day: the moments you lived with the people you love. With 200+ weddings under my belt, I use my expertise to guide my clients to feel comfortable and confident so their images feel like them. 

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