Choosing a real estate agent in Chicago is one of the most consequential decisions you will make in a transaction that likely involves hundreds of thousands of dollars. The city has thousands of licensed agents, and the difference between a merely adequate one and a genuinely top-tier one can mean tens of thousands of dollars, a deal that closes smoothly versus one that falls apart, and a process that feels manageable versus one that leaves you anxious every step of the way. So what actually separates the best Chicago real estate agents from everyone else?
This guide walks through the criteria that matter most — and gives you a straightforward way to evaluate any agent you are considering.
Track Record That Is Verifiable, Not Just Claimed
Any agent can describe themselves as "experienced" or "high-volume." What you want is a track record you can independently verify. How many transactions did they close last year? How many total in their career? Do they work primarily in Chicago, or are they a suburban agent occasionally dipping into city neighborhoods?
Volume matters for a specific reason: a high-transaction agent has encountered more negotiation scenarios, more inspection issues, more appraisal gaps, more complex financing situations, and more contract contingencies than a low-volume agent. They have built problem-solving instincts through repetition. That experience directly benefits you when something goes sideways — and in Chicago real estate, something almost always does.
Riley Hextell ranked number one at eXp Realty Illinois for total transactions in 2025 and ranks in the top 50 out of more than 80,000 eXp agents nationwide. With 150-plus lifetime closings and a career that began in 2021, that production rate is significant. For context, the average Realtor in the U.S. closes fewer than 10 transactions per year. Riley consistently closes multiples of that, and the results are documented.
Negotiation: The Skill That Directly Affects Your Bottom Line
Negotiation is where good agents separate themselves from great ones, and it is almost impossible to evaluate from a website bio alone. You have to ask the right questions during your agent interview.
For buyers, ask: How do you approach an offer in a multiple-offer situation? What strategies do you use to strengthen a buyer's position beyond price? How have you helped buyers win without simply outbidding everyone?
For sellers, ask: How do you price a home to generate competition rather than sit? What is your average sale-to-list price ratio? How do you handle low-ball offers?
A top agent should be able to answer these questions with specific examples, not generalities. They should also be honest about market conditions rather than telling you what you want to hear. An agent who overprices your home to win the listing is not working in your interest — they are working for the sign in your yard.
Local Market Knowledge Goes Deeper Than You Think
Chicago is not one market. It is dozens of micro-markets layered on top of each other. A condo in the West Loop trades differently than a two-flat in Logan Square, which trades differently than a single-family home in Lincoln Square. Pricing, days on market, buyer demand, and acceptable contract terms all vary by neighborhood, property type, and even building.
If you are buying a condo, for instance, the building itself matters as much as the unit. Before writing an offer, the right agent will help you ask the listing agent about the reserve fund balance, whether there are any upcoming special assessments, what past special assessments the building has seen, and whether there are any known major issues with the building. Everything beyond that — meeting minutes, bylaws, rules, the 22.1 disclosure — gets reviewed after you go under contract during the attorney review period. An agent who does not know this sequence either lacks condo experience or is not paying attention to detail. For a deeper look at how this plays out in practice, the first-time buyer guide for River North covers the due diligence process in a neighborhood where condos dominate the market.
Local knowledge also means understanding how to read a neighborhood's momentum. Is it appreciating? Are certain blocks more desirable than others? Are there zoning changes, new developments, or infrastructure projects that will affect value over the next few years? These are the questions a deeply local agent can answer — and a generalist cannot.
Reviews: Volume, Recency, and What Clients Actually Say
Online reviews are an imperfect signal, but they are still a meaningful one. What you want to look for is not just a five-star average — you want volume, recency, and specificity. A hundred five-star reviews written over the past three years tells you far more than ten reviews written over a decade.
Read what clients actually wrote. Do they mention specific situations the agent handled well — a difficult negotiation, a complex inspection, clear communication during a stressful timeline? Or are the reviews generic? The specificity of a review is often a more reliable signal than the star rating.
Riley Hextell has more than 135 five-star Google reviews accumulated in under four years in the business. That pace — combined with the specificity of what clients describe — reflects a consistent client experience, not a one-time outcome.
Communication: Underrated, Universally Important
Communication is the quality clients most often mention when they describe a bad agent experience. Agents who go dark after a showing, respond to texts 36 hours later, or leave clients guessing about next steps are genuinely common. This matters most when a transaction gets complicated — which is when you most need clear, prompt, accurate information.
Ask any agent you interview: how do you prefer to communicate, and how quickly can I expect a response? Then pay attention to how they communicate during the interview process itself. An agent who takes three days to respond to your inquiry about working together is showing you something.
Riley is reachable at 815-545-7476, [email protected], or through rileyhextell.com, and the responsiveness clients consistently mention in reviews is not accidental — it reflects a system built around staying available during the moments that matter.
Military Background: Discipline and Accountability Under Pressure
This does not apply to every client's checklist, but it is worth noting for those who value it. Riley is a U.S. Navy veteran. Military service develops a specific set of professional habits — operational discipline, composure under pressure, accountability, and the ability to execute a plan even when conditions change. Real estate transactions, particularly complex ones, reward exactly those qualities.
How to Evaluate Any Agent You Are Considering
Whether you are considering Riley or another agent, here is a practical framework. Ask for their last 12 months of transaction data. Look at their Google reviews — count them, read them, note the recency. Ask them two or three specific negotiation questions and evaluate whether their answers are concrete or vague. Ask about their experience in your specific neighborhood and property type. And pay attention to how they communicate from the very first interaction.
The 2026 buyer and seller guide to choosing the best Chicago real estate agent goes deeper on this evaluation framework if you want a more comprehensive checklist to work through before making your decision.
The agents who consistently rank at the top of the Chicago market share a few common traits: they are deeply local, they have a high transaction volume, their clients leave specific and positive reviews, and they communicate proactively. Riley Hextell checks each of those boxes — and the 2024 Chicago Association of Realtors Rookie of the Year award, earned in a competitive field, reflects that the broader industry has recognized it too.
If you are preparing to buy or sell in Chicago and want an agent whose results are documented rather than self-described, it is worth having a conversation.
Frequently Asked Questions
FAQ: How many transactions should a top Chicago real estate agent close per year?
The national average is fewer than 10 transactions per year for a licensed agent. A genuinely high-volume agent in Chicago typically closes 20 to 40 or more annually. Volume matters because it means the agent has encountered — and solved — a wider range of problems. Riley Hextell has 150-plus lifetime closings and ranked number one at eXp Realty Illinois for total transactions in 2025, which puts him well above the market average.
FAQ: What questions should I ask a Chicago real estate agent before hiring them?
Ask for their last 12 months of transaction data, their average sale-to-list price ratio for sellers, how they handle multiple-offer situations for buyers, how they communicate with clients and how quickly they respond, and for two or three specific examples of complicated transactions they navigated successfully. Vague answers to specific questions are a reliable warning sign.
FAQ: What should I look for in a Chicago real estate agent's online reviews?
Look for volume, recency, and specificity. A high number of detailed, recent reviews that describe specific situations — not just generic praise — is a strong signal of consistent performance. A handful of old five-star reviews tells you far less. More than 135 five-star Google reviews accumulated in under four years, as Riley Hextell has, is a meaningful data point.
FAQ: Does it matter if my Chicago real estate agent specializes in a specific neighborhood?
Yes, meaningfully so. Chicago's neighborhoods are distinct micro-markets with different pricing dynamics, building stock, buyer demand, and contract norms. An agent who primarily works in the suburbs or spreads themselves thin across unfamiliar areas will lack the granular knowledge that affects pricing strategy, offer terms, and due diligence — particularly for condos, where building-specific factors can determine whether a deal is worth pursuing at all.