Hi Dan, I want to make sure I understand your questions correctly.
You own a flat in the wonderful Lakeview area of Chicago, and you do not need to sell.
You would like to buy a single family home though, now my questions to clarify
a) if and when you decide to buy that single family home, will you then need to sell your condo?
b) where would you want to buy your single family home within the city or near city suburbs like
Glenview, Wilmette, Northfield etc.
Upgrading, selling and moving into a larger and generally speaking more expensive property is a good time to do so, as you have many choices, lower pricing, low interest rates and truly good negotiation possibilities!
You will most likely have to accept a little less for your own condo at this time, but you will save a larger bite on the larger single fam. home.
So as you can see, depending on what , the price range and where you are looking to buy it may make a difference whether this is the right time for you.
Feel free to contact me directly at email@example.com - I would gladly e-mail you a free pre market overview of your area and your type of property without home visit initially and I would also e-mail you available single fam. homes in the size, style, price range and locations you would like to explore. All arriving in your e-mail inbox with your choice to ask for additional information and you can make changes to your search criteria at any time.
Hoping to hear from you and I would love to assist you in your decision making process and in selling and finding your next home.
Edith YourRealtor4Life! Working always in the very BEST interest of her clients!