Thinking About a Move in 2026? Ask Yourself These Questions First
Joe Freeman December 29, 2025
Joe Freeman December 29, 2025
The end of the year has a way of slowing everything down—especially in the Chicago real estate market.
Showings taper off. Schedules open up. And for many homeowners and renters across neighborhoods like Lincoln Park, Wicker Park, West Loop, Lakeview, and Logan Square, one question quietly surfaces:
“Should we make a move next year… or stay put?”
If that thought has crossed your mind—even casually—you don’t need to decide anything today. But asking the rightquestions now can give you clarity, confidence, and leverage when the timing is right.
Below are seven questions every Chicago buyer or seller should consider before making a real estate move in 2026.
In Chicago, people rarely think about moving “randomly.” There’s usually a trigger.
Ask yourself:
Is this about a lifestyle shift—space, location, commute, schools, or walkability?
Are monthly costs, property taxes, or maintenance driving the conversation?
Are we feeling constrained, or simply curious about what options exist?
Understanding whether your motivation is discomfort or opportunity matters. Each leads to very different timelines and strategies in the Chicago market.
Many buyers and sellers ask, “Should we wait?”
A better question is: “What would need to feel clearer before we move?”
Consider:
Are we waiting on market conditions—or clarity in our own situation?
Is there a milestone involved (job change, school year, savings goal)?
If nothing changed for another year, how would that actually feel?
In Chicago real estate, the best moves aren’t rushed—they’re prepared.
Hesitation usually isn’t about headlines. It’s about uncertainty.
Ask:
Are we worried about overpaying, selling too low, or timing it wrong?
Is disruption, stress, or regret the bigger concern?
If we understood how to protect against these risks, would the decision feel easier?
Most fear fades with better information—not perfect market conditions.
Waiting can feel safe—but it’s still a decision.
Ask yourself:
Are we waiting for interest rates, prices, or confidence?
If those don’t change as expected, how long would we realistically wait?
What’s the opportunity cost of staying put for another year in our current home?
For many Chicago homeowners, clarity comes from weighing tradeoffs, not predictions.
Every Chicago home purchase or sale involves priorities.
Ask:
Is monthly comfort more important than long-term equity?
Are we optimizing for flexibility or maximum sale price?
Is minimizing stress more valuable than squeezing out every dollar?
There’s no universal “right” answer—but knowing yours simplifies every decision that follows.
Instead of trying to time the Chicago market perfectly, flip the perspective.
Imagine it’s late 2026 and you’re looking back:
What would make you feel confident about how you handled the move?
Would you regret rushing—or regret not preparing?
What version of this decision would feel intentional instead of reactive?
The best real estate outcomes usually come from planning, not guessing.
You don’t need all the answers—you just need fewer unknowns.
Clarity often comes from:
Understanding your realistic buying or selling range in today’s Chicago market
Knowing what options actually exist in your neighborhood (not just online headlines)
Having a flexible plan, even if your move is 6–12 months out
You don’t need to commit to buying or selling a home before you’re ready.
But if a move is even loosely on your 2026 radar, the smartest first step isn’t scrolling listings or reacting to market noise—it’s getting clear on what actually matters to you.
And if you want to walk through these questions with real numbers, local insight, and zero pressure, that conversation alone often brings more clarity than months of waiting.
Step into a world where your real estate journey is as unique as you are. With a focus on tailored strategies and a hands-on approach, Joe delivers a customized experience that turns your vision of luxury living into a reality.
