Best Chicago Engagement Session Locations
The Best Chicago Engagement Session Locations — From Your Photographer
After 7 years shooting in this city — I know every corner, every golden hour window, every hidden spot that makes Chicago look like a movie set. And I want to share all of it with you. 🤍
The question I get asked most often is: where should we do our engagement session? And I LOVE it. Chicago is one of the most photogenic cities in the world and there is genuinely no wrong answer — but there are definitely spots that will make your gallery absolutely unforgettable.
Here is my personal, tried-and-tested guide to the best Chicago engagement session locations — organized by vibe, because not every couple wants the same thing. 🥰
For the Classic Chicago Couple
The granddaddy of them all. North Avenue Beach is where you get that iconic Chicago skyline stretching out behind you, the lakefront breeze and the beach energy all at once. Classic and it never gets old.
Whether you want barefoot-in-the-sand or dressed up with the city as your backdrop — this location delivers every time. We work the whole stretch from the boathouse to the water's edge as the sun goes down. 🤍
Elegance, magnificent architecture and SO much variety in one session. The Riverwalk is romantic. We start at the Kinzie Bridge, walk the river, end at the La Salle Bridge — all within a few blocks and all of it stunning.
I have shot here in every season — summer evenings with the river glowing, fall with the leaves turning, winter with the city all lit up. It always works. 🤍
Can we talk about the Wrigley Building in Chicago for a second? Because it deserves its own moment. 🤍
Built in 1920 as the headquarters of the Wrigley chewing gum company, it was the first skyscraper on what would become the Magnificent Mile — when everything north of the Chicago River was still warehouses and factories. The gleaming white terra cotta facade is hand washed to preserve it. The clock tower was styled after the Giralda Tower of the Seville Cathedral in Spain. And it was the first landmark in Chicago to be floodlit at night.
Frank Sinatra even sang in his song "My Kind of Town" that "Chicago is… the Wrigley Building" in 1965. That is how iconic this place is.
Today it sits right where Michigan Avenue crosses the Chicago River — one of the most photographed spots in the city and one of my absolute favorite backdrops for Chicago engagement sessions. Every single time. 🥰
Those red bridges? ICONIC. The bridges along the Chicago River — Clark Street, La Salle, Wells Street — each one gives you a completely different feel. Architectural, bold, cinematic. The city rises up in every direction and the images always look like they belong in a magazine. 🖤
For the Nature + City Couple
A hidden gem and I am OBSESSED. The South Pond area gives you the feel of a forest preserve — lush trees, a gorgeous pond, nature everywhere — but you are still in the city with the skyline peeking through the trees.
Especially magical in spring when everything blooms and in fall when the leaves turn. Not enough Chicago couples know about this one. 🥰
📍 Lurie Gardens — Millennium Park
Right in the heart of Millennium Park, Lurie Gardens is one of Chicago's most underrated session spots. Lush perennial gardens, beautiful tall grasses, wildflowers and a completely different feel from anywhere else in the city.
It is intimate and romantic, best in late spring through fall when the gardens are fully alive. 🌿🤍
A permit is required.
📍 Milton Lee Olive Park
Chicago's best kept secret. Tucked just north of Navy Pier, this little park has water on three sides, unobstructed skyline views and beautiful green space — and almost nobody knows it exists.
We basically have it to ourselves. The light here at golden hour is breathtaking — the water catches the sky and everything glows. Romantic, quiet and completely magical. 🤍
📍 Chicago Museum Campus
Beautiful trees, flowers, stunning neoclassical architecture AND sweeping skyline views — all in one place. The lakefront path along the Museum Campus at golden hour is one of the most beautiful stretches in the city.
For the Art + Architecture Lover
📍 The Art Institute of Chicago Gardens
My absolute favorite place in all of Chicago — and I will stand by that forever. The McKinlock Court gardens are stunning. The ivy. THE IVY. Lush, romantic, full of character at every single turn.
In spring and summer it is completely alive with green. In fall it turns the most beautiful shades of red and orange. Every session here looks like it was shot in a secret garden in Italy. 🤍
Your answer for colder months, rainy days, or any couple who wants something completely unique. The Art Institute has the most breathtaking indoor spaces — grand staircases, soaring ceilings, incredible natural light through tall windows.
The best approach is to come right before opening — you get the space almost entirely to yourself. Admission fee applies (the price of a regular ticket) but the images are worth every penny. Cinematic, editorial, one of a kind. 🖤
One of the most jaw-dropping interiors in Chicago and it is completely FREE. The Chicago Cultural Center on Michigan Avenue has two stunning Tiffany glass domes, intricate mosaic details, marble staircases and grand halls that look like they belong in a European palace.
It is one of the most underused session locations in the city and I absolutely love it. Architectural, grand, and unlike anything else. Perfect for the couple who wants something truly unexpected. 🤍
📍 Chicago Union Station
Classic columns. Dramatic architecture. The Great Hall with its soaring ceilings, marble floors and gorgeous columns brings cinematic grandeur that is unmatched anywhere in the city.
If you have ever dreamed of that timeless, Old Hollywood, movie-still kind of portrait — Union Station is exactly where we are going. 🎬
📍 Chicago Board of Trade
Right in the heart of the Loop. Skyscrapers rising on every side, grand imposing architecture, electric city energy. Nothing says Chicago quite like standing in the middle of it.
Perfect for the couple who wants something urban, strong and undeniably city. Great for editorial vibes and fashion-forward moments. 🖤
📍 Merchandise Mart
One of the largest buildings in the world, sitting right on the Chicago River in the most beautiful way. The riverfront area around the Merchandise Mart gives you the building, the river, the bridges and the city all at once.
A little unexpected, a lot impressive. The images always look like they belong in a design magazine. 🖤
For the Luxury + Elevated Couple
📍 London House Chicago
ICONIC. The London House rooftop has panoramic 360 degree views of the Chicago skyline, Lake Michigan and the river all at once. The interiors are warm, luxurious and Art Deco inspired.
A reservation is required (around $500+) but the images are completely different from every other Chicago engagement session you have ever seen. If you want one of a kind — this is it. 🤍
For the Fashion Lover — Gold Coast
📍 Gold Coast — Rush Street + Division Street
If you have a killer outfit, a love for beautiful things and you want your session to feel like a fashion editorial — Gold Coast is calling your name. 🤍
Rush Street and Division Street are the most fabulous blocks in Chicago — stunning architecture, incredible restaurants, beautiful boutiques and that unmistakable Gold Coast energy that is completely its own thing. We walk, we window shop, we stop in front of the most beautiful storefronts and let the city be your runway.
Think strolling past Gibson's, walking by the most gorgeous boutiques, cocktail in hand, completely in your element. It feels less like a photoshoot and more like the most glamorous date night in the city — which is exactly how I want you to feel. 🥰
This is the session for the couple who dresses up, loves good food, appreciates beautiful design and wants images that feel elevated, chic and completely Chicago. Gold Coast never misses. 🖤
For the Bar + Restaurant Session
One of my absolute favorite ideas that not enough couples consider — a session inside a beautiful Chicago restaurant or bar. We use sharp, editorial flash lighting that creates this incredible moody, fashion-forward look that you simply cannot get outside.
Think: your favorite cocktail, a plate of pasta, a slice of pizza — something that is completely YOU. It relaxes you immediately, gives your hands something to do and leads to the most natural, candid moments.
My top two picks for a restaurant or bar session in Chicago is Gilt Bar and Tre Dita— and they could not be more different from each other, which is exactly why I love them both.
📍 Gilt BAR
The iconic restaurant Gilt Bar in River North is moody, intimate and absolutely stunning. Dark wood, warm candlelight, gorgeous bar details — it photographs like a dream and the flash lighting looks INCREDIBLE against those interiors.
📍 Tre Dita
The new and fabulous restaurant at the St. Regis Chicago is a stunning Italian steakhouse inside one of the most architecturally remarkable buildings in the city. The St. Regis was designed by the legendary Jeanne Gang of Studio Gang Architects — the world's tallest building ever designed by a woman — and the interiors match that energy completely. Beautiful, warm, sophisticated and completely unforgettable. Cocktail in hand, gorgeous surroundings, completely in your element. 🤍
Both are unforgettable. Both give you something completely different from any outdoor session. If you have been dreaming of something editorial, moody and uniquely Chicago — this is your answer.
The Most Unique Chicago Session — On the River
OK can we talk about this idea because I am OBSESSED. Chicago Boat Company has the most adorable retro boats — originally from the 1950s and 60s, lovingly restored with electric motors and Bluetooth speakers. They depart right from the Chicago Riverwalk at Wacker and State, in front of City Winery.
A 90-minute self-guided cruise on the Chicago River with your person, your favorite snacks and drinks, the city rising up around you on every side. I am on the boat with you, photographing the whole thing — the laughing, the floating, the Chicago skyline doing its thing in the background. 🤍
It is romantic, it is fun, it is completely different from every other engagement session out there. Up to 4 passengers so it works perfectly for a couple plus your photographer. Pricing starts at $275 for 90 minutes Monday-Thursday and $299 Friday-Sunday.
Fun Ideas to Make Your Session Uniquely You
The best sessions feel like YOU. So let's add something personal:
🌅 Sunset date night — cocktails, donuts, pizza, shakes, hotdogs — bring a prop, it helps with posing AND it's so fun
🚗 Moto or muscle car — instant editorial. If you have access to a beautiful car, let's use it
📸 Flash session at a restaurant or bar — sharp light, your favorite drink, moody and fashion-forward
🛥️ Retro boat on the Chicago River — 90 minutes, the whole city as your backdrop
🌊 The beach at golden hour — barefoot, relaxed, glowing. Summer evenings on Lake Michigan are UNREAL
☕ After-session snacks — boba tea, coffee, ice cream — the most candid real moments always happen here 🥰
So — Which Location is Right for You?
Honest answer: the location matters way less than the light, the connection and how comfortable you feel. I have gotten incredible images at every single spot on this list.
When we book I always set up an initial virtual conversation where we talk through your vision, your style, and which Chicago locations feel most like you. Because this session should feel like the best date night you have ever had — documented forever. 🥰
Chicago is one of the most beautiful cities in the world. Let's go shoot it together. 🤍
