Best Lawyers

Chicago’s Best Lawyers

You don’t want to need a lawyer. But when you discover that you do need one, it’s best to pick one of the best Chicago lawyers. It’s not the time to scrimp on quality.


Chicago is notorious for pushing the envelope—in business, in government, in crime, the Windy City lives on the edge. Scandals erupt, businesses go bust, crimes get exposed, and the courts don’t just throw the book—they throw the whole library.


Chicago and Illinois courts are notorious for harsh sentences and penalties handed down in courtrooms, to say nothing of the U.S. District Court for the Northern District of Illinois or the stringency of the Seventh Circuit Court of Appeals. It takes a special breed to be one of the best Chicago lawyers. 


Questions To Ask When Hiring A Lawyer in Chicago


Go ahead. Ask questions. Ask all the questions. Most attorneys ask and answer questions for a living—if they can’t take the heat of some tough questioning, that’s something you want to know up front, isn’t it? 


In fact, some lawyers are so good at answering questions, they might be able to glibly dismiss every concern. You want to be armed with the right questions that pierce through the blather and expose whether this is the right attorney for you. Here are some questions to ask when interviewing Chicago lawyers to represent you.


How Long Have You Been in Practice?

If the lawyer is fresh out of law school, that might be a red flag, especially if you face a thorny case or serious charges. Look for some longevity in the business. If the attorney is new on the scene, see if they can provide evidence that they are a hot shot whiz kid.


What Types of Cases Do You Handle?

Even an experienced attorney might be inappropriate as your counsel if they have not handled many cases like yours. A lawyer with decades of experience defending criminals in court might not be appropriate to handle a child custody hearing, for example.  


What Percentage of your Practice is Dedicated to My Kind of Case?

Law firms especially parcel out their practices into percentages. They may say that they practice real estate law, but if upon questioning you find out that only 5% of their practice is devoted to real estate law, you might want to seek out an attorney that devotes more time, resources, and expertise to cases that more closely resemble yours.


Who Is Your Typical Client?

This might sound like a repeat of some of the last questions, but it actually teases out different nuances. If you need representation as an individual, this question might expose the fact that the lawyer’s typical client is a corporation or trust. The attorney may be very good at this job, but may not be a match made in heaven for you.


How Many Cases Like Mine Have You Represented?

Years in business does not necessarily equate to similar cases tried. Find out how many times the lawyer has represented a case like this, and dig deeper to find out some of the outcomes. How many of those cases were won? Lost? Settled? Trust me, the attorney in front of you remembers. Get a clear answer.


What Special Training Do You Have That Is Relevant to My Case?

Law school isn’t the be-all, end-all of attorney training, especially for certain disciplines. Patent law, DUI defense, and other legal areas may require specialized training to make the attorney an effective advocate. An attorney with less experience but specialized training in your type of case may be the better choice.


What Is Your Approach or Philosophy to Cases Like These?

Note that what outcome the lawyer pursues can make a big difference, especially in criminal or divorce cases. A divorce attorney who is determined to gut every spouse may not be suitable for a divorcing couple seeking an amicable split. A criminal attorney who believes in plea bargains at all costs may not be the guy for someone facing stiff charges—10 years in prison may be unacceptable, but 2 years may be unacceptably disruptive as well. Consider looking for an attorney whose goal is to win.


Will Any Portion of my Case Be Handled by Associates or Paralegals?

This dovetails with billing. Ask if any hours of work handled by associates or paralegals are billed at a discounted rate. This is industry standard, but you sometimes have to ask.


What Is The Most Likely Outcome in My Case?

Get the attorney’s honest answer of what (s)he thinks is likely to happen at the conclusion of the case. It’s great if you hear an answer you want to hear, but it also tells you something about the attorney’s attitude, mindset, and confidence.


What Are My Options for Resolving This Case?

Find out if trial or negotiated settlement are your only options. Could your case be settled through mediation? Arbitration? What are the strengths and weaknesses of both approaches?


How Will You Keep In Touch with Me About Developments in My Case?

Figure out when and by what method your attorney will reach out to you. Get a timeline of important dates, and specify if you prefer phone, text, email, etc.


What To Look For When Seeking A Law Firm


With hundreds of law firms in Chicago to choose from, narrowing it down to the right one can seem like an intimidating task. Here are some criteria to use to evaluate law firms as you search.


Long Term or Short Term?

Some cases require a lawyer for the short term; sometimes you need to establish a relationship with an attorney or law firm for ongoing work. If you need long-term representation, make sure the attorney accepts that kind of work. As you meet representatives of the firm, try to decide if you feel comfortable with this firm as your counsel for the long hall.


Areas of Law

Most firms list their areas of specialty on their website. Make sure to ask about the firm’s experience, reputation, and outcomes in your case area, as well as the percentage of the practice dedicated to that area of law. 



In addition to getting referrals from family and friends and checking online reviews, check to see if they have accolades like a 10.0 Avvo rating, a Leading Lawyer or Top 100 Lawyers, or a Best Law Firm rating from US News and World Report.


Size of Firm

How many lawyers, paralegals, and support staff does the firm employ? A large firm might have resources to spare, but may relegate your case to support staff or treat you like a number. If you approach a bigger firm, get a sense of where your case will sit in their hierarchy and the personal touch you can expect.


Fees and Billing

Find out the retainer, hourly rates, per-case rates, and different billing for more experienced attorneys vs. less experienced attorneys. Find out what expenses (shipping, travel, etc.) will be billed separately or if they upcharge for trial preparation and trial hours. Make sure you can live with the fees and that there are no nasty surprises.


Character Compatibility

We place a great deal of trust when we hire a lawyer—this is our representation. Make sure that the law firm and its representatives demonstrate character and values that resonate with you, and that they take their burden of responsibility seriously. 



The most respected lawyer in the world is not worth the fee if (s)he doesn’t have time for your case and someone less qualified ends up handling it. Make sure the attorney is not so overworked that (s)he will neglect critical communication with you or give your case anything other than the careful attention it deserves.

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