Chicagoland Downsizing, Senior Moving, Estate Sale Solution Specialists!

 Gail Hampton CEO Caring Transitions of Chicago             

 Hello, my name is Gail Hampton. During my lifetime, I’ve seen as well as experienced my family and many other families struggle during some of life’s most stressful and overwhelming times, such as a life changing illness, the death of a loved one and the changing needs of an aging parent.  This compelled me to start Caring Transitions, a business that helps families, or anyone needing assistance, cope with the emotional and financial stress of relocating, downsizing or liquidating a loved one's personal belongings.

Our service to you begins with my extensive background in project management and consulting, and me personally handling my brother's estate. That service is expanded, complemented and supported by each member of my carefully selected staff. You can be assured that my staff and I will work with you to develop a blueprint for success to manage life changes while keeping your family’s best interests at heart. Our focus is to minimize your stress and maximize your returns while helping you through a difficult time in your family’s life. Our services include any or all of the following:

  • Senior Move Management
  • Full or Partial Liquidations
  • Estate Sales
  • Downsizing
  • Interviewing Attorneys, Realtors
  • Staging a House to be Sold
  • Cleanout and De-Cluttering
  • Special Projects

Let us take on some of the burden. Whatever activity you don't want to do or have time to do, delegate it to us so you can work on the things that can't be entrusted to someone else. We'll work with you to develop a detailed plan of action that fits your needs. Let us help simplify your transitions so you can have peace of mind. 

We are passionate about serving our clients and look foward to serving our community with courtesy, dignity and respect. We enjoy helping people. Caring is what we do!

Call us today to schedule a COMPLIMENTARY In-Home Consultation.



Gail Hampton and her team were a lifeline when my father died unexpectedly and I had to clear out and manage his 1925 Chicago bungalow while living 300 miles away. Gail was my “go-to” person during the two years it took me to make the multiple trips to Chicago to get the house ready for sale.

 First I went through all the contents of the house myself, removed some of the things I wanted, and labeled the rest. Then Caring Transitions came in and packed up my keepsake items and moved them to a storage locker.  There was not enough “good stuff” in the house for a conventional estate sale on location, so Gail arranged for online listings of the big-ticket items and successfully sold several of them. She donated what did not sell and what was usable from the rest of the contents, and gave me a detailed receipt for my taxes. There was an enormous amount of sheer trash, and because the house was no longer occupied, there was no City trash service and Gail’s team had to dispose of everything off-premises. Several times I had to arrange for repair people to come to the house, and Gail’s team always met them to give them access and to work with them. Gail periodically sent a team member to check the exterior and make sure it was secure. She supplied ongoing progress reports, detailed photos of the work in progress and of the final results, detailed descriptions, receipts for any supplies the team had to purchase, and any other documentation I needed.

Finally, when my realtor advised me to sell the house as-is except for having all the ancient wall-to-wall carpeting removed, Gail’s team did this project. It turned out to be a ghastly mess, because the carpeting was so old that the padding underneath had rotted away and either disintegrated into powder or fused to the floor. Gail’s team was very careful, and the hardwood floors were revealed needing only sanding and refinishing to be beautiful. In order to do a final damp-mopping, the team even brought in their own water because the pipes had frozen and burst so the house had no water service.

 Gail met with my realtor to do a final walk-through to see if anything else should be done before the house was listed for sale. The realtor didn’t see any other needs and told me Gail’s team had done “a magnificent job.” The punch line is that the house sold in 24 hours for 60% more than my asking price. The process of getting it ready had been long and arduous both logistically and emotionally, and Gail’s combination of empathy and efficiency was invaluable. I enthusiastically recommend Caring Transitions of Chicago.

 Barbara MacRobie  •  St. Louis, Missouri 



Dear Gail -

Thank you and your Caring Transitions of Chicago team for your help recently in liquidating my aunt's condo in Lincoln Park. You kept your promises and handled everything with integrity. I appreciated that so much, as I was overwhelmed with the responsibilities at hand. You communicated with me every step of the way and I found your assistance incredibly valuable. Thank you for doing such a difficult, yet thorough job!

Very Truly Yours,
Lynn K. Edisen  • El Cerrito, CA


Hey Gail,

Thank you so much for producing a miracle in my apartment at 400 E. It looks so beautiful.

Ms W Brown • Chicago, IL

Everything looks amazing!! Thank you to you and your fantastic team. You turned her house into a home and Mom is over the moon!

Ms T Brown McGee • Chicago, IL


Gail Hampton and the Caring Transitions team made a difficult time a lot easier both physically and mentally. With the recent death of my mother, I didn't have the know how to deal with the amount of items that my mother had in her apartment of 45 years. They handled an overwhelming situation effectively and efficiently with the utmost care and patience. I was impressed with their ability to identify important items and bring them to me. I'd like to thank Gail, Gwen, Pat and Jonathan for their support and assistance during this challenging time.

Mr Wm  • Chicago, IL


 Dear Gail:

Many thanks for the outstanding job you and your staff did handling the estate sale at my mother-in-law’s home.  It was a daunting task and you approached it with professionalism and efficiency.

From the initial cleanup and sort of items, to the sale itself and the final clean out; I realized how valuable your services are.  The staff assisting you were all very friendly and courteous throughout the entire process.  I can’t tell you what a relief it was to walk into the house after the sale and see the rooms completely empty.  Special thanks for coordinating the final pickup of items donated to charity.

I would recommend your services to anyone.  Please feel free to list my name as a reference.


Brian Pechtold, CPA  Hampshire, IL


 I am an art dealer in St Louis and I was recently contacted by Gail Hampton of Caring Transitions in Chicago.  Ms. Hampton emailed me a photo of a painting that was included in an estate she was handling.  She told me that she had researched the artist, and had discovered that I bought and sold works by that painter, and she wanted to know if I had interest.  As it turns out, I was, because it was a very good example.  Gail had contacted other galleries, but after setting up an appointment for me to see the painting, I ended up being the buyer--paying over twice his record price at auction.  I was happy to get such a good example and didn't mind paying the price--but what really impressed me was the professionalism and the capability of Ms Hampton and her organization.  I thought to myself that her client was really fortunate to have someone who cared about doing such a good job and going the extra mile.  Gail knew that to get the real value from the estate she needed to contact different people for different things--and in this case, even in different cities.  She also spoke respectfully of the owner, and had done a nice job organizing and displaying the material.  I would recommend her service to anyone.

 Thom Pegg • Owner of Tyler Fine Art • St Louis, MO and
         former Director of 20th Century Art & Design • Heritage Auction • Dallas, TX
Having a house sale  that represents 30 years of your life is not only emotional;  it is mentally exhausting.  But if you have Gail Hampton  ( Caring Transitions) in your corner, this will be an amazing experience.  Gail’s detailed efficiency and  expertise balances perfectly with her care and concern for you, your house and your life’s possessions. DO NOT take this journey without Gail Hampton.
JoAnne Stone-Geier • Owner More in Store • La Grange Park, IL


Anyone would agree that relocating is one of the most stressful of life experiences. Certainly that is compounded innumerable times over when one is also dealing, as my family was, with the recent death of our father, moving our mother to assisted living and coping with her new Alzheimer’s diagnosis, while emptying out our family’s home of over forty years – with its accumulation of valuable art, unusable trash, old familiar items of furniture, and uncountable memories.  

Gail Hampton and the Caring Transitions staff came in with their skill, professionalism, great sensitivity, understanding and caring. With their help a situation that appeared to be completely unmanageable and overwhelming was handled with efficiency and thoughtfulness.   They took care of an estate sale to sell all of the items of value, including evaluating, photographing and cataloging all the items in the home, appropriately advertising the sale, and overseeing the sale itself. Ms. Hampton was also conscious of the special items that filled a unique niche, and contacted specific collectors to arrange individual sales of those items ahead of time. She then arranged for charitable donations of any items which they were not able to sell, and then cleaned and de-cluttered anything remaining in the apartment.

Caring Transitions’ pricing structure was very reasonable. Their work was very thorough and professional. Most importantly, they were kind and caring. Our family cannot thank Gail Hampton and her company enough for all of their support and assistance during this challenging time.

Ora Prochovnick • San Francisco, CA
I recently acquired the services of one of your franchises. The young lady that helped me was Gail Hampton. If it were not for Gail, I would still be working on my Mother’s apartment. The kindness of Gail and her staff made me feel like family was digging in to help. Her kind heart shown through in all she did. Even when the sale was over, she went beyond the call of duty to continue to contact buyers, donation places, etc. I am so very happy to have found Gail. She left her mark on my life. I will be forever grateful to her. She will be in my heart for a long time. Thank You Gail.  The family of Elaine Ortmann 
Janet Johnson • Elgin, IL



Our employees are very important to our success. The quality of our services depends upon the caring professionals who are a part of our team. If you are looking for part-time work in a service that’s appreciated, contact us today. Caring Transitions needs compassionate, trustworthy, dependable people to help make our transition services the total solution for families coping with Senior Moves, Downsizing, or Estate Sales.

Become one of our Caring professionals today. Contact Us!

Consultation for Estate Sale, Senior Moving, and Senior Relocation
When you need help with one of life’s changes, find your total solution with Caring Transitions. Request a COMPLIMENTARY In-Home Consultation today to simply learn more about the services we provide. Contact us with any questions you have about our Senior Moving, Downsizing, Estate Sales and other services. Your satisfaction is guaranteed!
Gail Hampton, CRTS, CSA
Certified Senior Advisor
17 East Monroe • Suite 130 • Chicago, IL 60603
(312) 545-6717
Downtown, Near North, Near West, Near South and Surrounding Chicagoland Area
Estate Tag Sales & Auctions
Sale Listings Coming Soon!
Visit Our Online Store! -

VIEW, BID and BUY items from our local estate sales and more - online! Click the link below to visit our online store.

 read more ...

Local Partners
Updates Coming Soon



Settling An Estate -

 What Do You Need To Know?

 read more ...

With Change Comes Stress -

 Learn to Stress Less

 read more ...

Role of a Fiduciary -

 Something You Should Know

 read more ...

A Difficult Home Transition -
People, Money or Things -

 Which has the "real" value?

 read more ...

Are You in Transition This Holiday Season? -

 Remember - Treasure Things You Love & Need ~ Repurpose the Rest

 read more ...

Should I Move or Age-In Place? -

 How do I decide?

 read more ...

For A Successful Sale -

 "Set the Stage" 

 read more ...

Securing Your Valuables -

 Takes organization and action

 read more ...

What You Love -

 Can be treasured or repurpose 

 read more ...

Mother's Day -

Caring Ideas

 read more ...

Spring Cleaning -

Tips for Organzing Your Garage

 read more ...

End-of-Life Planning -

Plan ahead for peace of mind

 read more ...

Choosing Your Mover -

For a smooth transition

 read more ...

Universal Design -

A growing trend in homes

 read more ...

Improving Communication during a Major Life Transition -

Tools for success

 read more ...

Watch this video to learn more about our services!

Each Office is Independently Owned and Operated.
© 2008-2012 by CT Franchising Systems, Inc. | Terms Of Use | Privacy Statement | Login