Jill Cunningham

Jill Cunningham


30 Green Bay Road
Winnetka, IL 60093

Why Jill Cunningham? 

A third-generation Realtor, I have been in real estate sales and financing for 13 years. While my specialty is in residential real estate sales, I have vast expertise that includes working in commercial real estate finance. This has given me the ability to assist clients in securing loans, as well as helping them with the task of making important financial decisions.  I speak the complex language of finance, and have the ability to relay that information in a way that anyone can understand.

Born and raised in the area, I am intimately aware of all that the Chicago and North Shore neighborhoods have to offer.  With a calm and engaging personality, I am the kind of person people enjoy being around. I am compassionate when it comes to my clients, and passionate about what I do. Far from soft, I am a bulldog when I need to be, and work hard to make deals happen.

In addition to spending time with my husband and two children, I dedicate much of my time at Children’s Memorial Hospital.  I serve on the Family Advisory Board and volunteer in many other areas of the Hospital.

Key Points 

Licensed agent for over 13 years

Third-generation Realtor

Expert in residential real estate sales

Experience with commercial real estate sales

Prior to real estate, worked in banking, venture capital, and trading international commodities

Member of Family Advisory Board at Children's Memorial Hospital

Parent Wise Volunteer at Children's Memorial Hospital

BSBA from Marquette University with minors in Economics and Spanish

Clients are saying:

"Jill Cunningham and Cam Benson are professional and experienced brokers. They are experts at pricing and marketing homes in the Edgebrook neighborhood. They provided us with excellent advice on preparing and staging our house before going on the market. They listened to our needs and requirements regarding timing and access to our house. We had several complicating factors that added a few additional challenges for them and they easily maneuvered and accommodated our needs. Another quality that makes both of them so effective is that they are attentive to prospective buyers without being "pushy." Our house sold quickly thanks to their help and professional expertise. I recommend them to anyone who is ready to place their house on the market."

"Selling a home can be a very emotional and physically draining process. Without Jill and her partner, Cam, I would have never made it. They were there to guide me toward the right timing, staging and pricing. They were always available for me, other brokers and inspectors for questions, advice and meeting anyone at the property. I felt as if they were actually looking out for me and the property. When it came to negotiation, they were fantastic and again always looking out for my best interest. I would highly recommend them to anyone interested in selling their home."

"Jill was absolutely amazing! She was a pleasure to work with. Jill was always available whenever we had questions or concerns. She is very knowledgeable, and I would highly recommend her. Since we were first time home buyers, she really helped us every step of the way. Jill even came to our closing just to congratulate us. She made the whole home buying experience very enjoyable!"

"Always helpful and truthful throughout the entire process beginning to end. Jill and Cam always returned my calls and answered my endless questions. I would use again if I was in the same area."

"Jill is wonderful. Always willing to answer every question I have (and I have a lot) or refer me to someone who can best inform me. She will also help us on a moment's notice, she is available whenever we need her. Jill has become a friend, and someone we strongly trust."

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