Chicago Rooftop Wedding at Homestead on the Roof | Emily + Ben

Weddings

When Emily and Ben began the search for their wedding photographer they had clear goals in mind: someone who could document their day in a way that’s authentic to them, both in the candid moments as well as the more traditionally posed portraits. They also wanted to make sure they vibed well with their photographer, and from my point of view I think they succeeded on all fronts. Documenting Emily and Ben’s wedding at Homestead on the Roof in Chicago was a literal dream. These two have such a pure and fun love for one another, which made this day such a tremendous joy to be a part of.

Simple blue wedding invitation with pink flowers and gold and silver wedding rings sitting on light wood floors.

Getting Ready for Their Wedding in Chicago

Those that know Emily and Ben are well aware of the lighthearted, fun loving energy about them, and that same whimsical joy was present throughout each and every moment of their wedding day. From getting ready the morning of with their favorite people, to dancing the night away at Homestead On the Roof in Chicago, their wedding was one of endless celebration!

A bride stands with her bridesmaids laughing the morning of her wedding. She's wearing a white linen pajama set and her bridesmaids are wearing oversized blue button ups. They're getting ready for the wedding day in a Chicago hotel.

I’m getting ahead of myself though, let’s jump back to the start of their beautiful day. Both Emily and Ben kicked things off by getting ready in the company of their closest friends and family. In the comfort of their hotel in downtown Chicago, the two made the most of each and every moment with their loved ones. Good vibes, tons of laughter, and endless smiles, their morning had it all. After taking their time and feeling the love from their friends and family, it was soon time for Emily and Ben’s first look.

A bride looks out the window towards the sky scrapers of Chicago including the John Hancock building.
A bride stands in the corner of her hotel room with white and black walls, she's wearing a white linen pajama set and a silk wedding robe with white sunglasses in her Chicago hotel.
A bride gets lipliner put on her lips she's backlit by a large window overlooking the city of Chicago.
A bride stands with her back to the camera while a bridesmaid uses a crochet hook to button up her wedding dress.
A bride sits in her Chicago hotel room the morning of her wedding laughing with a bridesmaid. The bride is wearing a draping strapless dress with simple white satin heels with a toe strap and an ankle strap. The bridesmaid is wearing a hot pink dress with a strappy back.
A black and white image of a grooms suit hanging on a wall in a Chicago hotel room.
A groom puts on his belt the morning of his wedding getting ready with a sibling in his Chicago hotel room.
The sister of the groom laughs at the groom as he gets ready in his Chicago hotel.

It was a moment of pure happiness when Emily and Ben saw one another for the first time in their wedding attire. Throughout my years of photography I don’t think I’ve met a couple that are as obsessed and in love with one another as Emily and Ben. As you’ll see from their first look onward, these two hardly took their eyes off one another for the entire day.

A bride and groom stand together seeing each other for the first time on their wedding morning just outside of their Chicago hotel. The bride is wearing a romantic pleated strapless dress with buttons going down the back bodice.
A bride and groom see one another for the first time on their wedding day. The brides pleated dress looks beautiful in the shadows of the cloudy Chicago wedding day.
A bride and groom have a moment together the morning of their wedding outside of their Chicago hotel. The bride wears a pleated grecian inspired strapless wedding dress. The groom is wearing a simple black sport coat with an open button up shirt.
A close up black and white image of a groom hugging his bride the morning of their wedding you can see the brides loose curls and the grooms arms wrapped around her waist.
A reflection in a window of a skyscraper of a bride and groom sharing a moment together outside of their Chicago hotel room. The bride and groom are out of focus, and the leaves are starting to change on the trees behind them for fall.
A bride and groom embrace the morning of their wedding. The bride drapes her arms over her grooms shoulders holding a bouquet with pink and white wedding flowers. Her dress is filled with pleats emulating a grecian style bodice.
A close up documentary style image of a bride and groom holding hands and embracing the morning of their wedding just outside of their Chicago hotel room.
A bride and groom walk along side skyscrapers in the Loop in Chicago. The bride laughs and the groom has his arm behind her back as they walk towards the camera.
A bride and groom stand along Michigan Avenue by the River Walk in Chicago. The bride laughs and the groom is holding the train of her grecian inspired wedding dress. She holds a wedding bouquet filled with textured flowers like daisies and dahlias.
A bride and groom walk along Michigan Avenue by the River Walk in Chicago. The bride laughs and the groom is holding the train of her grecian inspired wedding dress. She holds a wedding bouquet filled with textured flowers like daisies and dahlias in shades of pink.
A bride and groom laugh with their wedding party on a Chicago wedding trolley. The bridesmaids are wearing hot pink wedding attire and sunglasses.
A groom and bride walk along the riverwalk in Chicago surrounded by skyscrapers to take wedding portraits on their wedding day. The bridesmaids wear shades of pink and the groomsmen wear navy blue suits with casually buttoned white shirts.
A groom is carried by his wedding party in Chicago for wedding party portraits surrounded by skyscrapers.
A bridesmaid tosses her wedding bouquet in the air and makes the bride laugh as all of the bridesmaids cheer on the bride during wedding portraits. In the background of the bridal portraits you can see the Chicago river and many Chicago skyscrapers.
A bride and groom hold each other and passionately kiss overlooking the Chicago river. The image is in black and white and is just of the upper body of the newly-weds.
A bride and groom kiss while holding one another overlooking the Chicago River. The bride is wearing a grecian inspired pleated dress with a train and is holding a wedding bouquet made up of flowers in shades of pink.
A bride and groom kiss and hug candidly during their Chicago wedding portraits.
A bride and groom stand looking off into the distance. The bride shows off her elegant pleated wedding dress by holding the train out to the side. The groom is dressed casually for his Chicago wedding.
A bride and groom dance and laugh together during their wedding portraits overlooking the Chicago river. The bride is wearing scrappy stiletto white heals and a grecian inspired pleated wedding gown. The groom is wearing a navy blue suit.
Chicago skyscrapers including Mercantile Mart overlooking the Chicago river.
The legs of a bride and groom walking together through the streets of Chicago in a black and white image.

Some Karaoke Before Their Wedding Ceremony at Homestead on the Roof

As a fan and proponent of alternative wedding portraits, I was over the moon with excitement when Emily and Ben told me that they planned on incorporating karaoke at Louie’s Pub into their wedding day. Not only was this soooo much fun for them and their wedding party, but it actually happens to be where these two first met! That’s right, their love story began in literal High School Musical fashion! After this trip down memory lane, as well as some stellar karaoke from the group, it was all aboard the party bus as we made our way to Homestead on the Roof.

A karaoke dive bar in Chicago during the fall with wedding guests waiting for the arrival of the newlyweds.
A photographer takes a photo through the window of a dive bar in Chicago of a bride and groom talking with guests before their wedding day.
A bride laughs as she approaches the bar with her groom on their wedding day.
A bride and groom sing together at their favorite Chicago bar before their intimate wedding day.
A bride and groom sing karaoke together the afternoon before their wedding in a dive bar in Chicago.
A groom laughs with his bride as they sing a song in a dive bar in Chicago on their wedding day with their wedding party.
Wedding guests sing karaoke together at a dive bar in Chicago.
A guest sings with the bride and groom on their wedding day at a Chicago karaoke bar.
A bride and groom laugh together while watching their guests celebrate them at their favorite karaoke bar in Chicago.
A bride illuminated by blue light with an applause sign behind her sings a son on karaoke with all of her bridesmaids.
A bride sings with her bridesmaids the afternoon of her wedding in a Chicago karaoke bar. The bridesmaids are all dressed in shades of hot pink.
The groom plays air guitar while singing karaoke at Louie's pub in Chicago before his wedding day. He sings with all of his wedding guests.
Two wedding guests sing together and pose for a photo at Louie's Pub in Chicago.
The groom stands while holding a microphone in his hand up in the air at Louie's Pub in Chicago on his wedding day.
A bride poses with a bridesmaid celebrating her wedding day on a Chicago Trolley. The bridesmaid is wearing a hot pink bridesmaid dress and a pair of light pink glasses.
A bride and groom sing and dance together on their Chicago wedding trolley on their wedding day.
A bride and groom sit together holding hands and laughing as they mentally prepare for their wedding ceremony at Homestead on the Roof in Chicago.

Homestead on the Roof is a lovely, charming wedding venue in the heart of Chicago’s West Town. This venue felt perfect for Emily and Ben’s day as it is both remarkably beautiful, and also an incredibly comfortable and welcoming space. It’s the ideal setting for a wedding like this where the planned events of the day are just as important as the moments and memories made with those there to celebrate Emily and Ben. After a heartfelt and emotional rooftop ceremony, Emily and Ben were officially newlyweds which meant it was time to party!

Wedding guests pose for a group picture sitting on the ground together at a rooftop wedding venue in Chicago.
Two ring bearers wrestle with one another wearing boat shoes, and shortsleeved white button ups with vests. They're attending a wedding at Homestead on the Roof.
A bride and groom laugh together while holding hands as the photographer documents this moment through a small doorway. They're waiting together for their Chicago wedding ceremony.
Bridesmaids pose for a funny photo at a Chicago rooftop wedding venue dressed in hot pink bridesmaids dresses.
Guests wait for the wedding ceremony to start at the Chicago rooftop wedding venue.
A guest in a black suit and green tie laughs with another guest before the outdoor rooftop wedding ceremony in Chicago.
A bride poses for a quick photo with her dad before her Chicago wedding ceremony starts.
A bride and her father walk down the aisle to her groom on her wedding day. She's holding a bouquet of pink dahlias and daisies for her fall wedding in Chicago.
The groom hugs his brides father, you can see the back of the brides head in the foreground.
A bride and groom get married in the ceremony space at Homestead on the Roof, a Chicago rooftop wedding venue.
The groom laughs with his whole face at something his bride says during their wedding ceremony. His groomsmen dressed in navy blue suits also laugh in the background.
Bridesmaids stand in their hot pink bridesmaids dresses holding small bouquets of pink dahlias and ranunculus.
A bride laughs with her whole face while holding the hands of her groom during their Chicago rooftop wedding ceremony. A bridesmaid stands behind her in a hot pink dress holding two bouquets of dahlias.
A bride and groom kiss concluding their rooftop wedding ceremony in Chicago. Their guests sit under a covered structure and there are string lights hanging throughout the venue.
A blurry image of a bride and groom celebrating as they exit their wedding ceremony space on a Chicago rooftop.
A groom dips his bride as they walk down the aisle after their Chicago rooftop wedding ceremony at Homestead on the Roof.
A bride and groom laugh and celebrate with guests as they walk down the aisle after their ceremony at their Chicago rooftop wedding venue Homestead on the Roof.
A bride celebrates and looks at the camera as she leaves her the ceremony space of her wedding venue Homestead on the Roof.

An Unforgettable Wedding Reception at Homestead on the Roof

If it seems like the flow of Emily and Ben’s wedding day is perfect for them, that’s because it was. These two thankfully booked my fav wedding planner, Bridget Mary Weddings, who made sure that every part of their wedding day was seamless. Homestead on the Roof also played a huge role in this, as the multiple spaces available allowed the ceremony, cocktail hour, and reception of Emily and Ben’s wedding to take place one after the other. 

A bride and groom have an intimate moment alone on the rooftop of their wedding venue before heading into Homestead On the Roof for their intimate wedding dinner.
The bride and groom kiss during their wedding reception at Homestead on the Room in Chicago.

Much like the rest of this one of a kind wedding day, Emily and Ben’s reception was filled with so many memorable moments. An epic entrance with members of the wedding party being iced? Check. A series of emotional, heartfelt, and hilarious speeches? Check. Some beautiful first dances on the light up dance floor? Check. An epic dress change from Emily before a night of all out dancing? Also check. It was seriously a night like none other, and I’m so glad to have been able to experience and document it all.

The bride and groom enter their wedding reception inside Homestead on the Roof surrounded by guests. The groom gives a toast to their guests.
Guests shout and laugh with one another as they celebrate their loved ones at Homestead on the Roof in Chicago.
Two guests kneel and drink Smirnoff Ices at a wedding reception in chicago at Homestead on the Roof.
The father of the bride gives a toast during their intimate wedding reception at Homestead on the Roof.
The groom toasts one of his groomsmen during dinner at their wedding reception in Chicago.
Wedding guests sit together telling stories during an intimate wedding reception in Chicago.
The bride and groom laugh together while a bridesmaid shares a story during her wedding toast. Their reception is in the indoor portion of Homestead on the Roof.
A bridesmaid in a hot pink wedding dress stands in front of a simple periwinkle blue seating chart sign as she gives a toast to the bride and groom who are in the foreground of the photo.
Guests make a toast to the bride and groom at Homestead on the Room in Chicago.
A bride and groom walk onto the lit dance floor that is lined with their guests for their first dance. The rooftop wedding venue in Chicago is lit with string lights and the lighting within the dance floor.
A bride and groom share a first dance on a lit dance floor that is lined with their guests for their first dance. The rooftop wedding venue in Chicago is lit with string lights and the lighting within the dance floor.
A bride and groom share a first dance on a lit dance floor that is lined with their guests for their first dance. The rooftop wedding venue in Chicago is lit with string lights and the lighting within the dance floor.
A bride and groom share a first dance on a lit dance floor that is lined with their guests for their first dance. The rooftop wedding venue in Chicago is lit with string lights and the lighting within the dance floor.
A crooked image of guests rushing the dance floor of a Chicago rooftop wedding venue lined with string lights.
A bride and groom sing and dance together surrounded by guests at their Chicago rooftop wedding venue that is lit by string lights and lights in the dance floor.
A bride has her bridesmaid put her hair up in a pony tail before returning to the dance floor on her wedding day. She changed into her reception outfit which is a beaded gown designed by Clio Peppiatt.
A bridesmaid kneels on the bathroom floor to help her bride put on her champagne colored wedding shoes in the elegant bathroom at Homestead on the Roof.
The bride stands up against the wall of the bathroom in Homestead on the Roof the rooftop wedding venue in Chicago. The bride is wearing a beaded wedding reception dress designed by Clio Peppiatt.

It’s hard to imagine a more fitting day to celebrate the wonderful love between Emily and Ben. From reliving the start of their relationship at the karaoke bar they met at, to an unforgettable wedding at Homestead on the Roof, their day was a perfect representation of the incredible love they share. 

A bride and groom dance together on the dance floor, the bride is wearing her wedding reception dress designed by Clio Peppiatt covered in beads.
Wedding guests gather around the bride and groom to dance and sing at their wedding reception in Chicago. A bridesmaid is in the foreground singing towards the camera with light pink sunglasses and a hot pink dress.

Check out more of my work here, and if you’re looking to book me as your photographer head over to my contact page!

Vendors

Photography: Emma Petersen Photography

Planner: Bridget Mary Weddings

Venue: Homestead On the Roof

Hair & Makeup: Windy City Glam & Glam and Glow by Mel

Florist: Cou Cou Studios

DJ: Green Line Talent

Caterer:  Homestead On the Roof

Getting Ready Robe: Arthur + Lucca Custom

Ceremony Dress: Essense of Australia

Reception Dress: Clio Peppiatt 

Tux: Blvdier

Rings: Ethan Lord Jewelers 

Brides People Attire: The Black Tux

Cake/Desserts: West Town Bakery

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