There is a particular kind of family conversation I suspect is happening around a lot of Chicagoland dinner tables right now.
It starts innocently enough.
What if Mom sold her house and moved closer to us?
Or:
What if instead of helping our adult kids afford a condo, we bought something together?
Or:
What if we found a two-flat and everybody had their own space?
And then someone asks the question that tends to stop the whole conversation:
Okay... but how would that actually work?
That is where multigenerational living gets interesting.
Because once you stop imagining six people cheerfully sharing one kitchen forever and start looking at the actual housing stock around Chicago, Oak Park and the near-west suburbs, there are a lot more possibilities than people realize.
One thing Chicagoland has going for it is an enormous supply of older housing that was not necessarily designed around today's idea of one nuclear family occupying one completely self-contained house.
Chicago has two-flats, three-flats and homes with separate levels, rear entrances and surprisingly flexible layouts.
Oak Park, River Forest, Forest Park, Berwyn and other nearby communities have large older homes, multifamily properties, coach houses and buildings that have evolved through several generations of family life.
And accessory dwelling units, or ADUs, are increasingly part of the housing conversation too, although what is legally possible varies significantly by municipality and property.
In other words, multigenerational living around here does not necessarily mean squeezing Grandma into the guest bedroom.
Sometimes it can mean:
Close, but separate.
And I think that distinction is everything.
This is the part families often do not calculate.
Imagine one household owns a home worth $650,000 with a relatively small mortgage remaining.
Another household owns a $400,000 home with some equity but is juggling a much larger monthly payment.
Individually, everyone may feel somewhat stuck.
But what happens if both properties are sold?
How much usable equity would the family actually have?
What are both households currently spending each month on mortgages, property taxes, insurance, utilities and maintenance?
What could those combined resources purchase?
And perhaps most importantly:
Would the new arrangement actually improve anyone's life?
Those are very different questions from simply asking, "How expensive of a house can we buy?"
That is why I built a free Multigenerational Home Planner specifically to let families play with the possibilities before anyone makes a major decision.
Try the free Multigenerational Home Planner
You can model different households, existing homes, equity, contributions and potential shared housing costs to see whether an idea that sounds good around the dinner table also makes sense on paper.
And sometimes the answer may be surprisingly promising.
Sometimes it may be absolutely not.
Both are useful information.
There is another number I wish every family considering this would calculate:
How much togetherness can everybody actually tolerate?
Because saving money is lovely.
Privacy is also lovely.
A beautiful 4,000-square-foot house with six adults sharing one kitchen may technically provide enough square footage and still make everyone bananas.
Meanwhile, a Chicago two-flat could give two households their own kitchens, living rooms, bathrooms, entrances and routines while keeping grandparents, parents and kids one staircase away.
That can create some genuinely interesting possibilities.
Grandparents can be nearby without surrendering their independence.
Parents may have help with childcare without coordinating a 45-minute drive.
Adult children can potentially build financial stability without living in their childhood bedrooms.
Families can share maintenance, outdoor space or certain expenses while keeping other parts of their lives separate.
And someone can make coffee at 5:30 in the morning without conducting a family meeting about it.
This is where browsing multigenerational homes becomes very different from ordinary house hunting.
A listing might have six bedrooms and still be terrible for two generations.
Another property might have only four bedrooms but an almost perfect arrangement because it has:
And accessibility matters too.
If the plan includes aging parents, the charming third-floor primary suite may not remain charming forever.
First-floor bedrooms, fewer stairs, wider passages and the possibility of adapting a bathroom can matter enormously.
This is why I would not start a multigenerational home search by simply typing "5+ bedrooms" into Zillow.
You are not really shopping for bedrooms.
You are shopping for a way for multiple households to live well together.
This part is considerably less Instagrammable.
Who owns the property?
Whose name is on the mortgage?
What happens if one household contributes substantially more cash?
If a parent puts $300,000 of equity into the purchase, is that a gift, an ownership interest or a loan?
Who pays for a new roof?
What happens if someone wants to move?
What happens after a death?
What if someone's financial circumstances change?
What if the living arrangement simply does not work?
These are not reasons to abandon the idea.
They are reasons to involve the right professionals before buying anything.
Depending on the arrangement, families may need advice from a lender, real estate attorney, estate-planning attorney, accountant or financial planner in addition to their Realtor.
The goal is not merely figuring out how to purchase the property.
It is making sure everyone understands what they are agreeing to.
I actually think one of the healthiest questions a family can ask is:
What happens if we hate this?
Could part of the property be rented?
Could one household buy the other out?
Would a two-flat retain usefulness and resale appeal even if the family arrangement changed?
Could an ADU eventually serve another purpose?
A flexible property gives a family options.
And options matter when you are making a decision that mixes money, housing and people you would presumably like to continue inviting to Thanksgiving.
This may be the most important part.
I do not think multigenerational living is automatically a better way to live.
For some families, it could be transformational.
For others, the financially optimal arrangement may turn out to be two homes five minutes apart.
The point of running the numbers is not to prove that everyone should pool their equity and buy a giant house together.
It is to turn a vague family conversation into something concrete enough to evaluate.
What do we own?
What do we owe?
What are we collectively spending now?
What could we afford together?
What kind of property would actually give everyone enough independence?
And finally:
Would this make our lives better?
If your family has been having some version of this conversation, you can start by playing with the numbers yourself using my free Multigenerational Home Planner for Chicago and the near-west suburbs.
No commitment to buy anything. No requirement that Grandma move downstairs.
Just a much better starting point than, "You know what we should do someday..."
Laurie Christofano is a Realtor with RE/MAX In The Village serving Oak Park, Chicago and the near-west suburbs. She helps people navigate the housing decisions that tend to come with life's next chapters, including downsizing, relocating, combining households and figuring out whether moving makes sense at all.
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