I couldn’t imagine a more romantic day than getting married on Valentine’s Day at the incredible St. Michael’s Church in Old Town, Chicago!

This romantic black tie winter wedding in Chicago had everything you could dream of: a stunning Valentine’s Day celebration filled with heartfelt moments, timeless style, and a magical snowy night. The bride began her day getting ready in a beautiful loft Airbnb in Chicago’s West Loop neighborhood—an ideal getting ready location with natural light and historic charm. Her bridesmaids wore champagne-colored dresses and shared happy tears and laughter as they boarded a vintage white trolley to the ceremony. Their happy teared, emotional ride through the city was one of the sweetest parts of the day, filled with excitement and anticipation. There were so many sweet hugs and happy tears from mother of the bride and mother of the groom on that drive – some of my favorite photos from the day!

The ceremony took place at the historic St. Michael’s Church in Old Town Chicago, a breathtaking setting for their Catholic wedding. The bride wore a classic satin gown from The Altar Bridal, styled with a beautiful layered cathedral-length veil and satin gloves for a timeless bridal look. Her father greeted her at the trolley before walking her into the church with her maids of honor.

After the ceremony, we headed downtown for wedding portraits at the Old Post Office in Chicago, which is hands-down one of the best wedding photo locations in the city. With its grand architecture and bright light, it was the perfect backdrop for both wedding party and family photos. Huge thank you to the events team there for helping us secure our photo permit! From there, the celebration continued with a romantic, candlelit wedding reception at Venuti’s Banquets, a popular wedding venue known for its elegant atmosphere, great food, and classic ballroom feel.

The reception was full of thoughtful details and vintage charm—white rose floral arrangements, glowing candlelight, a martini bar, and a four-tiered wedding cake with vintage piping and the same cake topper used at the bride’s parents’ wedding. One of the most magical moments of the night was when it started to snow during dinner—you could see the snowflakes falling outside the windows during speeches, and the couple snuck out after dinner for stunning snowy wedding portraits that truly captured their love for winter.

If you’re planning a wedding in Chicago or looking for Valentine’s Day wedding inspiration, this day was the perfect blend of classic romance, family-centered joy, and unforgettable celebration. From the heartfelt hugs after the ceremony to a dance floor that stayed full all night, this wedding was a true reflection of love, laughter, and legacy.