You typed something like “best estate planning attorney Chicago” into Google. Or maybe “estate planning lawyer near me.” Either way, you’re here because you know you need help and you’re trying to figure out who to trust with something that matters a great deal to your family.
That’s a good instinct. Estate planning is one of those areas where the wrong attorney can cost your family more than the right one would have charged. Not because they’re dishonest, but because they’re not paying close enough attention to details that only surface after you’re gone. By then it’s too late to fix anything. A Chicago, IL estate planning lawyer can help ensure every detail is handled correctly so your wishes are honored and your family is protected.
Here’s what to look for, what to ask, and what to watch out for.
Look for a Focused Practice, Not a General One
A lot of attorneys offer estate planning as one item on a long menu. They handle car accidents, real estate closings, traffic tickets, DUIs, and sure, they’ll also draft a will. That’s not the same as an attorney whose practice is built around estate planning and probate administration.
Illinois has its own estate tax with a $4 million threshold that functions completely differently from the federal exemption. It has specific rules about powers of attorney, living trusts, transfer on death instruments, and small estate affidavits. The state recently raised the small estate affidavit limit to $150,000 and excluded vehicles from the calculation. A general practitioner may know these things exist in a broad sense. A focused estate planning attorney lives in them every single day and understands how they interact with each other.
When you’re evaluating someone, ask how much of their practice is dedicated to estate planning and probate. If the answer is less than half, keep looking. You want someone who thinks about these issues constantly, not someone who dusts off a template once a month.
Ask About Illinois Specific Tax Planning
This is where a lot of estate plans fall apart quietly. Illinois is one of a handful of states that imposes its own estate tax, and it kicks in at $4 million. That sounds like a lot until you start adding things up. A house in the Chicago suburbs, a couple of retirement accounts, a life insurance policy, and maybe a small business or a rental property. Families cross that $4 million line without realizing it, and when they do, the tax hits hard.
Illinois also uses what’s called a cliff tax structure. If your estate is worth $3.99 million, you owe nothing. If it’s worth $4.01 million, the tax doesn’t just apply to the $10,000 over the line. The calculation effectively taxes the entire excess, and being barely over the threshold can generate a tax bill that wipes out the overage completely. It’s one of the harshest estate tax structures in the country.
Meanwhile, the federal estate tax exemption is now $15 million per person thanks to the One Big Beautiful Bill Act. That’s a massive gap. Your estate can be completely clear of federal estate tax and still owe six figures to Illinois.
Any estate planning attorney you hire in Chicago needs to understand both systems and build a plan that accounts for the gap between them. If you sit down with someone and they never mention the Illinois estate tax, or they assume the federal exemption covers you, that’s a red flag.
Make Sure They Talk About Funding the Trust
This is the single biggest mistake in estate planning, and most people don’t know to ask about it.
An attorney drafts a beautiful trust document. You sign it in their office. You pay for it. You walk out feeling like everything is taken care of. Then nobody moves your assets into the trust. The house stays titled in your name. The bank accounts stay in your name. The investment accounts stay in your name. When you die, the trust is technically empty and your family ends up in probate court anyway. The whole point of the trust was to avoid exactly that, and it failed because nobody did the follow through work.
A good estate planning attorney will walk you through the funding process in detail. They’ll explain which assets need to be retitled into the trust, which ones should use beneficiary designations instead, and which ones might use a transfer on death instrument. More importantly, they’ll follow up with you to make sure it actually gets done. Some firms handle the retitling themselves. Others give you a checklist and instructions. Either approach is fine as long as the conversation happens.
If someone drafts a trust and hands it to you without discussing funding, they’ve done half the job. And half a job in estate planning is often worse than no plan at all, because it gives your family a false sense of security.
Check Their Reviews, but Read Between the Lines
Google reviews are a reasonable starting point, but look for specific patterns rather than just the overall rating. Are clients mentioning that the attorney explained things in plain language? That they felt heard during the process? That the office was organized and responsive? That the follow up was good? Those are the details that actually predict what your experience will be like.
A five star average with vague, generic reviews doesn’t tell you much. Phrases like “great attorney, highly recommend” are nice but not informative. A slightly lower average with detailed reviews about real experiences, where clients describe what happened and how they felt about it, tells you a lot more about what it’s actually like to work with that person.
Also look at how the attorney responds to negative reviews. Do they get defensive? Do they ignore them entirely? Or do they respond professionally and try to address the concern? That response tells you something about how they handle problems in general.
Consider Accessibility and Communication
Estate planning involves sensitive conversations about money, family dynamics, health, and death. You want an attorney who is easy to reach and responsive when questions come up. That matters during the planning process, and it matters even more after the plan is signed.
Ask how they handle communication. Do you get a direct phone number or does everything go through a front desk? Can you email the attorney directly and expect a response within a day or two? If you call with a quick question six months after signing your documents, will they take the call?
Life changes. Laws change. Illinois has seen multiple legislative updates in just the last year that affect estate plans. You want an attorney you can call when something shifts, not one who considers you a closed file the minute you walk out the door.
What Questions Should You Bring to the First Meeting?
A good first consultation is really a two way interview. You’re evaluating the attorney just as much as they’re evaluating your situation. Here are the questions that will help you figure out whether someone is the right fit for your family:
How much of your practice is estate planning and probate?
You want at least 50 percent, and ideally more. This tells you whether estate planning is their focus or an afterthought.
How do you handle the Illinois estate tax?
They should be able to explain the $4 million threshold and the cliff tax structure without hesitation, and describe how they typically plan around it.
What does the funding process look like after we sign the trust?
If they don’t bring this up on their own, ask directly. Their answer will tell you whether they’re in this for the long haul or just the document drafting.
What happens if I need to update my plan later?
Estate plans are not a one time event. Laws change, families change, assets change. A good attorney builds a process for ongoing updates and makes it easy to come back.
What are your fees and how are they structured?
Get clarity on this upfront. Flat fee structures are common in estate planning and generally easier to budget for than hourly billing. There’s nothing wrong with asking.
Will you be the one doing the work?
In some firms, you meet with a senior attorney but a junior associate or paralegal does most of the drafting. That’s not necessarily a problem, but you should know how it works before you commit.
The Bottom Line
The best estate planning attorney for your family is someone who focuses on this area of law, understands Illinois specific rules, and treats your plan like an ongoing relationship rather than a one time transaction. Don’t pick someone just because they’re the cheapest option. Don’t pick someone just because their ad showed up first on Google.
Pick someone who asks you good questions, explains things without jargon, and makes sure the plan actually works after you sign it. That’s the difference between a plan that protects your family and a stack of documents that sits in a drawer. Kravets Law Group provides guidance focused on making sure your plan truly works when it matters most.
The Illinois State Bar Association maintains a helpful overview of estate planning basics at isba.org/public/guide/estateplanning. It’s a good primer to review before your first meeting with any attorney.