Honestly, I feel like winter weddings don’t get enough praise. While yes I understand that many don’t enjoy winter weddings especially with Chicago temperatures dropping into the negatives, I love to be able to find the beauty in moments. Yes… even moments standing in the freezing cold. For Alli and Dan’s special day, we are taking it back to New Year’s Eve of 2021. A day that symbolizes new beginnings and is honestly the perfect excuse to get married. Go into the new year with a new attitude, fresh mindset, and fresh new marriage! Alli and Dan’s Chicago New Year’s Eve Winter Wedding was one to remember and I’m so excited to be sharing it with you.

From Co-Workers to Lovebirds

Alli and Dan first met at a party that was thrown by their mutual friend from work. As Alli approached the bar to order a drink, she noticed Dan sitting at the bar beside her. His charismatic personality and jokes instantly caught Alli’s attention and she was hooked. Over time they would see each other around the office whenever Dan was in town. It wasn’t until 7 months later that they went on their very first date. Moral of the story here people… if it’s meant to be, it will be!

It wasn’t until one Sunday morning when Alli and Dan’s lives would change forever. They both got ready for a Sunday morning hike up to the Griffith Park Observatory in Los Angeles, California with their dog. While Alli didn’t know entirely what was about to happen, she did notice Dan’s change in demeanor. Just saying… we know ALL! Once they arrived at the observatory, they stopped at a lookout of downtown LA where Dan got down on one knee and proposed. It was such a special and memorable moment. So much so, that when they look out from their apartment balcony and see the observatory in the distance it reminds them of this wonderful moment.

The Getting Ready Process

I arrived at the Sheraton Grand Chicago Riverwalk Hotel where I met up with Alli and her bridesmaids getting ready. During this time I took some photos of Alli and her bridesmaids in their getting ready pajamas which were just the cutest. As soon as everyone was finished with their final touches, it was time for the lovely bride-to-be to put on her dress. Alli was wearing a fitted A-line dress with a gorgeous train with an insanely beautiful open back + removable tulle cape. To say I was stunned would be an understatement. She looked absolutely breathtaking and can we also take a moment to appreciate the Betsey Johnson boots she wore?? Sparkles galore and looked oh so amazing and really gave off those New Years Eve vibes, ya know?

While I was with the bridal party, the second photographer headed over to be with Dan and his groomsmen at The Gwen. Having a second photographer is the perfect opportunity to make sure no moments go uncaptured on your wedding day. While I may not be present to capture this moment, having a trusty second photographer is the best option to make sure every moment is cherished.

One moment in particular that was especially important was Dan opening his wedding gift from Alli. Upon first glance, it looked like a normal box. However you soon came to find out that it was actually a reel view-master filled with images of Alli & Dan. Honestly this gift is one that is so unique + clever and I loved that we were able to capture this moment and Dan’s reaction.

Wedding Day Tip

If you’re in a crunch for time, make sure that the bride is the first one to be finished getting ready. That way if time comes for the first look or portraits, the bride is able to go while everyone else finishes their final touches.

The First Look

It was really important for Alli and Dan to incorporate a first look on their wedding day. It’s an intimate moment between the couple and it gives you a bit of alone time before all of the craziness occurs and you’re surrounded by friends + family. Outside of Alli’s hotel, Dan stood there waiting for his gorgeous bride-to-be to arrive. The anticipation was building and as soon as he turned around you could see his eyes light up. Every moment after that became a blur as they both just soaked up this moment… this was it! The moment they had been waiting for was finally here and sinking in and it was oh so beautiful.


After coming down from that “first look high” we walked around the exterior of the hotel along the river taking some portraits of the two lovers. The weather was a bit cloudy and of course… in the middle of December so we really braved it for this one but it was so worth it. For winter weddings I always suggest bringing along a coat/coverup because 9/10 times you will get very cold if we are taking portraits outside. After some time taking solo portraits, the wedding party then joined us for some photos before we packed it up and headed to their venue.

Chicago New Years Eve Winter Wedding

Alli and Dan had both their ceremony and reception at Salvatore’s here in Chicago. Tucked away in Lincoln Park, this Chicago wedding venue is the perfect wedding location if you’re looking for something a bit more intimate. Alli and Dan both chose this Chicago wedding venue because of the wood-paneled walls and checkered floor. It really gave off that historical Chicago feel which both of them loved!

The ceremony inside the space was so beautiful and intimate and was one that was so beautiful to photograph. Alli walked down the aisle with her dad as she saw Dan waiting there at the altar. It’s also important to note that they had an unplugged ceremony. An unplugged ceremony is when guests are encouraged to turn off their cell phones and other devices in order to be fully present during your wedding. This can in turn prevent any phones getting in any photos that your wedding photographer is taking, but it allows for less distraction and more presence. Within a blink of an eye Alli and Dan were officially pronounced husband and wife and the crowd went wild! By crowd I totally mean their wedding guests but you know what I mean – lol.


The reception was filled with a lot of laughter and teary-eyed moments and tbh… I wouldn’t have had it any other way. Salvatore’s catered the entire wedding and the food was delicious! After eating dinner we went through speeches, which are always so fun to listen to. It really is a great way for me to learn even more about my couples which hey, I’m here for! We ended the night with some cake cutting and first dances with Alli + Dan and then each other with their parents.

As soon as the first dances were over, the dance floor opened up and everyone started cranking out their dance moves. I swear some guests practiced these moves for weeks, I was heavily impressed. One of the main reasons that Alli and Dan had a New Years Eve wedding was because of Dan! His 40th birthday was on January 1st, so they spent the reception singing happy birthday and enjoying his early birthday cake. What a perfect way to go into the new year, right? I left this Chicago New Years Eve Winter Wedding feeling so energized and eager to edit these photos. Cheers to Alli + Dan!

Oh and I’m just saying… if you loved this Chicago New Years Eve Winter Wedding, then you’re going to love this Bed + Breakfast Winter Elopement!

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Photography: Iron + Honey Photography

Wedding Planner: Sholeh Events

Bridal Gown Designer & Shop: Rosa Clara & Le Marriage Couture

Jewelry: Cassandra Lynne

Shoes: Betsey Johnson

Hair & Makeup: Elle Artistry

Tuxedos/Suits: Indochino

Florist: Floral Wonders

Caterer: Salvatore’s

Cake: Sweet Mandy B’s

Music/DJ: Green Line Talent

Stationery: Truly Engaging

Transportation: Windy City Limousine

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