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We love shooting weddings.  There are so many parts that make it fun.  This day had so many special features that will always make it stand out in my mind!  Cassie found me on Instagram and I knew from the moment we started chatting that we would be a great match.  She is a creative business owner, she loves all things weddings, she is extremely detailed and specific, she cared so much about the photography for her day, and she wanted all her loved ones to feel comfortable and taken care of– and this day delivered in every single area!  We absolutely adored DC Estate Winery on the Illinois/Wisconsin border.  It was truly an amazing Venue– gorgeous ceremony space, rolling hills, beautiful vines, nice indoor facilities, lovely reception space…it had it all.  And then when Cassie and Matt filled it with their friends, family, and their spirit of joy and fun it just all came together so perfectly!

Cassie and Matt are just a bit of everything together…they are fun, adventurous, meaningful and connected all at the same time.  They have lived around the country together, never hesitating to go where their love took them.  I just have truly enjoyed getting to know them and am so excited to share this day!  Cassie and Matt, we are so honored that you chose us as a part of your “dream team”– here are some of our very favorites from your day (and by some I mean a TON because we could not choose!!)!

One of my favorites of Michael’s from the day! Ceremony time!! Their sweet best man, Tucker, arrived just in time (see above!)! Their favorite pup (who’s bandana says “I do too”!!) is watching them get married…I just love it! Cassie made so many beautiful acrylic pieces for their decor! I also have to comment on the eucalyptus, which I have always loved.  It made for such a SIMPLE and STUNNING reception centerpiece (and there were sprays of it just everywhere!)…I just loved how one single colored simple flower made such a HUGE impact all over their day!  It was truly perfect.
This is the perfect guestbook for a winery wedding! LOVE these…we took some time walking around to get these sunset portraits and they are some of my favorites of the day– I am so thankful Cassie and Matt wanted these! I feel like this building could be STRAIGHT out of Tuscany!  After spending a summer in Italy in college studying music and culture, this totally spoke to my heart!   So many sweet, hilarious, and heartwarming moments in toasts!  I feel like you get to know a lot about a couple during toasts and I learned just how adored these two are in these moments, as if I didn’t already know. They had SUCH an active dance floor! I adore this #jillgumbride!!! And the last moments of light.  Cassie and Matt, we are SO thrilled for you– sending you love all the way to Charleston!!

To see this beautiful couple’s state park engagement session, click here!

We had so much fun working with Cassie and Matt’s amazing creative team (or the Dream Team as they called it!).  Cassie is an entrepreneur herself and truly assembled a phenomenal team to help bring her and Matt’s vision to life!

Venue: DC Estate Winery

Wedding Planner: Tia Laswell with Capstone Occasions

Flowers: Gary with White Rose Florist

Bride’s Dress Store: Vera’s House of Bridals

Dress Designer: Justin Alexander

Bridesmaids Dresses: Morilee from Vera’s House of Bridals

Tuxes: Custom Suits from Jos A. Bank

Videographer: True Shots Studios

Hair Stylist: Tifany Petra Loeffler from Bridal Beauty On Site

Makeup artist: RD Artistry

DJ: A Personal Touch DJ

Caterer: Thunder Bay Grille


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  1. […] Wedding Photographer: Jill Gum Photography […]

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I'm Jill, a wedding and portrait photographer based out of Chicago and Central Illinois, and available world wide! I'm also a photography educator, wife to my favorite person on the planet, mama to 3 amazing kids and an energetic Aussie, and obsessed with statement jewelry and all desserts (especially fruit pies!). 

As a past high school teacher, I have a major heart for education. After going full time in my business, I have built a business I love that gives me an almost 6 figure salary and allows me to be home part time with my kids.  I dream for you to run a business that enhances your life and lights you up, and I believe I can help you learn how to do it with a little hustle and a lot of heart!

click to learn more about me

Hello Friend!

Are you a Photographer?

Start HERE! 

Are you a mom/hobbyist?

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You're in the right place!  As a past high school teacher, educating others is my life's work and a HUGE part of my business!  I have been teaching moms and hobbyists how to use their camera from first purchasing it all the way to coaching them into businesses of their own, and I'd love to help you as well, wherever you are (and whatever camera you have!).

I'm so glad you are here!  Teaching Photographers and other small business owners how to run more joyful, successful, and profitable businesses is one of my favorite parts of my business!  I specialize in working with photographers to make their goals a reality (or figure out what their goals should be in the first place!).  

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