Intimate Chicago Wedding at Cindy’s Rooftop – Terrence & Shawn

Terrence and Shawn’s Cindy’s Rooftop wedding in September was one for the books. When I first heard from these two, they told me of how they met, their dog Clover, and 2019 engagement. Like many other couples, their original wedding plans were affected by the pandemic… which brings us to Cindy’s!

After a little re-planning, these two decided to tie the knot in an intimate ceremony at one of Chicago’s most iconic locations. Shawn and Terrence got ready with their families at the stunning Chicago Athletic Association Hotel overlooking downtown. They read personal letters to each other before meeting on the marble staircase for their happy first look! Before the ceremony, we had a chance to take photos inside the hotel and in the gardens at Art Institute of Chicago (my fave!). This crew was a blast to hang with – I love that they included their siblings as the wedding party!

Finally, it was time to get these two married. Terrence’s father officiated the ceremony on Cindy’s terrace, and I don’t think there was a dry eye among us! As soon as the knot was tied, cheers and applause erupted from their guests… and also patrons at the restaurant!! It was truly an unforgettable moment. Positive energy filled the air for these two the entire evening 🙂

Terrence and Shawn: Thank you again for having me in September!! Your Cindy’s Rooftop wedding was a highlight of my season. I wish you nothing but the best in Married Life!

Want to see more Terrence & Shawn? Check out their Sunrise Engagement Session featuring pup Clover!

Two grooms kiss on marble staircase before their Chicago Athletic Association Hotel wedding at Cindy's Rooftop
Entrance to Chicago Athletic Association Hotel downtown Chicago
Custom navy and gold invitation suite with wedding bands and groom details for September Cindy's Rooftop wedding
Navy and gold invitation with wedding bands and groom details for Cindy's Rooftop wedding
Detail photo of navy and gold invitation with groom details before Chicago Cindy's Rooftop wedding
Groom's details and cologne at Chicago Athletic Association Hotel before Cindy's Rooftop wedding
Groom adjusts bowtie in hotel room before Cindy's Rooftop wedding ceremony
Groom gets ready before Cindy's Rooftop wedding ceremony
Groom gets ready in Chicago Athletic Association Hotel room before Cindy's Rooftop wedding
Groom's details, shoes, and watch in Chicago Athletic Association Hotel room before Cindy's Rooftop wedding
Groom getting ready in hotel room at Chicago Athletic Association before intimate Cindy's Rooftop wedding
Groom ties his bowtie in mirror before Cindy's Rooftop wedding
Groom puts on his shoes before Cindy's Rooftop wedding
Groom walks down marble staircase toward groom for first look before Cindy's Rooftop wedding
Happy grooms hold hands during first look before Cindy's Rooftop wedding
Groom and groom hold hands in Drawing Room before their Cindy's Rooftop wedding ceremony
Two grooms sit by the fireplace before their Cindy's Rooftop wedding
Grooms hold hands during their first look before Cindy's Rooftop wedding ceremony
Grooms and their wedding party walk across Chicago's Michigan Avenue before Cindy's Rooftop wedding
Grooms and wedding party pose in the gardens at the Art Institute of Chicago before their Cindy's Rooftop wedding
Candid photo of happy grooms and their wedding party before Cindy's Rooftop wedding
Two grooms and their Chicago wedding party walk through the Art Institute South Gardens
Wedding party holds neutral-toned bouquets in the garden of the Art Institute of Chicago before Cindy's Rooftop wedding
Grooms and groomsman smile in the gardens at the Art Institute of Chicago before Cindy's Rooftop wedding
Two grooms dance outside in the Art Institute of Chicago South Garden before their Cindy's Rooftop wedding
Grooms smile at each other before their fall Cindy's Rooftop wedding
Two grooms hold hands in the South Garden of the Art Institute before their Cindy's Rooftop wedding
Creative wedding photo of grooms standing in busy Chicago street with traffic going by
Cincy's Rooftop restaurant sign for private event
Cindy's Rooftop wedding reception venue located in the Chicago Athletic Association Hotel
Custom dinner menu with plate setting for Cindy's Rooftop wedding reception
Welcome sign for Cindy's Rooftop wedding reception
Detailed photo of name place card for Cindy's Rooftop wedding reception
Name place card with greenery and florals for Cindy's Rooftop wedding reception
Detailed photo of ceremony program for Cindy's Rooftop wedding
Reception table candlelit with greenery for Cindy's Rooftop wedding
Detailed photo of Cindy's Rooftop wedding reception room with brick fireplace
Reception table details of florals with greenery and candlelight for Cindy's Rooftop wedding
Bird's eye view overlooking Chicago's Millennium Park from Cindy's Rooftop wedding venue
Floral centerpiece with neutral-tones with greenery for Cindy's Rooftop wedding
Groom and his mother walk down the aisle before Cindy's Rooftop wedding ceremony
Groom and mother hug before Cindy's Rooftop wedding ceremony
Groom and groom stand at the altar during their intimate Cindy's Rooftop wedding ceremony
Wedding guest reads poem during Cindy's Rooftop wedding ceremony
Groom's mother watches son exchange vows during Cindy's Rooftop wedding ceremony
Groom gets emotional during Cindy's Rooftop wedding ceremony
Groom reads vows during Cindy's Rooftop wedding ceremony
LGBTQ couple exchange rings during intimate Cindy's Rooftop wedding ceremony
Wedding guests watch same-sex couple exchange vows during their Cindy's Rooftop wedding ceremony
Just married grooms kiss during outdoor wedding ceremony at Cindy's Rooftop terrace
Just married grooms walk down the aisle after their Cindy's Rooftop wedding ceremony
Beer and wine selection for Cindy's Rooftop wedding reception
Signature cocktail with ice bucket for Cindy's Rooftop wedding reception
Bird's eye view of Millennium Park with Chicago Skyline from Cindy's Rooftop terrace
Cheese and vegetable appetizers on table for Cindy's Rooftop wedding reception
Vegetable appetizers on table with wild flowers for Cindy's Rooftop wedding reception
Appetizers on tray for Cindy's Rooftop wedding reception
Mini lobster roll appetizers served on wooden tray at Cindy's Rooftop wedding reception
Family-style Caesar salad served on farm wood table at Cindy's Rooftop wedding reception
Grooms deliver speech during Cindy's Rooftop wedding reception
Candid photo of happy grooms delivering a speech during their Cindy's Rooftop wedding reception
Wedding guests listen to groom deliver speech during intimate Cindy's Rooftop wedding reception
Grooms father delivers speech during Cindy's Rooftop wedding reception
Grooms smile at each other during their Cindy's Rooftop wedding reception
Groom's mother listens to groom's speech during Cindy's Rooftop wedding reception
Candid wedding photo of two grooms laughing during Best Woman speech at intimate Cindy's Rooftop wedding
View of Lake Michigan at sunset from Cindy's Rooftop terrace
Double exposure wedding photo of two grooms kissing with sunset at Cindy's Rooftop in Chicago
Night photo from Cindy's Rooftop wedding reception of Chicago skyline
Grooms cut vanilla wedding cake at their Cindy's Rooftop wedding reception
Detailed photo of Chicago Athletic Association Hotel at night
Just married grooms embrace in the middle of downtown Chicago
Candid photo of newlyweds outside of Chicago Athletic Association Hotel after Cindy's Rooftop wedding
Nighttime photo of newlyweds hugging in the middle of Michigan Avenue after Cindy's Rooftop wedding
Happy couple pose in the middle of the street in downtown Chicago after their Cindy's Rooftop wedding
Romantic night photo of newlyweds at the end of the night after their Cindy's Rooftop wedding
Grooms show off wedding bands outside of Cindy's Rooftop wedding reception

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