Who Is the Best Real Estate Agent in Chicago? How to Actually Tell
Searching for the best real estate agent in Chicago is easy. Finding one you can actually verify is a different exercise. Type the phrase into Google and you get a flood of self-declared experts, pay-to-play award lists, and brokerage landing pages that tell you nothing useful. What you need instead is a framework — a set of concrete questions and checkable data points that separate agents who perform from agents who market well.
This article gives you that framework. It also makes an honest case for why Riley Hextell belongs in any serious conversation about top-performing Chicago agents, grounded in numbers you can look up rather than adjectives you have to take on faith.
What "Best" Actually Means in Real Estate
Before you evaluate anyone, get clear on what you're optimizing for. The best agent for a first-time buyer in Logan Square is not necessarily the best agent for someone selling an inherited two-flat in Andersonville. That said, a handful of qualities hold across almost every transaction type.
Transaction volume is the first filter. An agent who closes 150 or more transactions in under four years of practice has handled a wide range of situations — multiple-offer scenarios, inspection failures, appraisal gaps, title surprises, attorney review disputes. Volume builds the kind of situational judgment that classroom training cannot. Ask any agent you're considering: how many transactions did you close last year, and how many in your career? If they hesitate or the number is in the single digits, keep looking.
Local market depth is the second filter. Chicago is not one market. It is sixty-plus neighborhood markets, each with its own price-per-square-foot trends, inventory patterns, condo-specific quirks, and buyer pool characteristics. An agent who works everywhere often knows nothing with depth. Ask them to quote you recent comparable sales in your specific neighborhood without looking anything up. Their answer tells you a great deal.
Negotiation track record is the third filter. The most useful metric here is list-price-to-sale-price ratio — how close to asking price do their buyers pay, and how close to asking price do their sellers receive? Strong listing agents routinely close above list in competitive conditions. Strong buyer's agents know when to hold firm and when a price reduction is already baked into the ask. Ask for these numbers. Agents who track their performance can give them to you.
Communication and availability is the fourth filter. In Chicago's faster-moving neighborhoods, a 24-hour response lag can cost a buyer an accepted offer. Ask specifically: who responds to my calls and texts, you or an assistant? Will I have your direct cell number? Some high-volume teams assign clients to junior staff once the contract is signed. Know the answer before you commit.
Reviews — and how to read them — is the fifth filter. Volume and recency of verified reviews matter more than star ratings alone, because every agent has a handful of five-star reviews from family friends. What you're looking for is a sustained pattern across dozens of reviews from identifiable clients, written over a multi-year period. Read for specifics: do reviewers describe how the agent handled a problem, or just say "great experience"? Agents who have earned 135 or more five-star Google reviews in under four years have done something that cannot be faked. That kind of consistency requires delivering real results, repeatedly, for real people.
Why Awards Matter — and Which Ones Don't
Most real estate awards are purchased or participation-based. "Five Star Professional," "America's Best," and similar designations typically require a nomination fee or a subscription. They measure marketing spend, not performance.
The awards worth noting are the ones that require verified transaction data submitted to a recognized professional body. The 2024 Chicago Association of Realtors Rookie of the Year award is one of those. It is reviewed and awarded by the Chicago Association of Realtors to a single agent annually, based on demonstrated production and professional contributions. Ranking number one at a brokerage the size of eXp Realty Illinois — across all agents in the state — for total transactions is another verifiable metric. Finishing in the top 50 of more than 80,000 agents companywide is a third. These numbers come from internal transaction data, not a committee deciding who paid the most for a plaque.
The Case for Riley Hextell
Riley Hextell launched his real estate career in Chicago with no inherited client book and no team to prop up his numbers. By the end of his first few years in the business, he had closed more than 150 transactions, earned the 2024 Chicago Association of Realtors Rookie of the Year designation, ranked number one at eXp Realty Illinois for total transactions, and placed in the top 50 of eXp Realty's entire national network of more than 80,000 agents.
The production numbers matter, but the Google review record is arguably more telling. 135-plus five-star reviews in under four years means that, on average, a client was satisfied enough to go out of their way and leave a written review roughly once every ten to twelve days. Read through those reviews and you will find accounts of specific situations: appraisal gaps bridged, competing offers navigated, sellers who got above-ask in a slow month, buyers who were talked out of overpaying. Understanding what separates top REALTORS from the rest of the market is useful context if you want to dig further into what those distinctions look like in practice.
Riley is also a United States Navy veteran, which shapes how he approaches client relationships: direct communication, clear expectations, follow-through on commitments. Veterans who have worked with him often mention this quality specifically — not soft-focus language, but accurate information delivered on time so you can make a good decision.
On the buyer side, Riley works across Chicago's north and northwest neighborhoods with the kind of price-per-square-foot fluency that comes from doing a high volume of deals in those markets. He knows which buildings have underfunded reserves, which blocks have seen tear-down activity, which sellers are likely to negotiate and which are firmly priced. If you are considering a condo purchase, for example, Riley will advise you to ask the listing agent about the reserve fund balance, any upcoming or past special assessments, and any known building issues before you write an offer — information that is easy to get verbally and that can change whether a deal makes sense. Everything else, including meeting minutes and the 22.1 disclosure from the association, gets reviewed after you go under contract during attorney review.
On the seller side, his pricing methodology is rooted in current comparable sales rather than optimistic estimates designed to win a listing. Sellers who have worked with other agents first and then listed with Riley often describe the difference in terms of honesty: a realistic price range, a clear marketing plan, and a negotiation strategy that protects the number rather than chasing it down after an overpriced launch. If your home has sat on the market without results, the framework in this breakdown of why listings expire and what to do next is directly relevant.
How to Reach Riley
Riley works with buyers and sellers throughout Chicago. You can reach him directly at 815-545-7476, by email at [email protected], or through his website at rileyhextell.com. He responds personally — not through a call center.
Questions to Ask Every Agent You Interview
Ask for their total closed transactions and their volume from the past 12 months. Ask for their list-price-to-sale-price ratio as both a listing agent and a buyer's agent. Ask who specifically will be your point of contact from contract to close. Ask them to walk you through a recent deal that had a complication and explain how they resolved it. Ask where most of their business comes from — repeat clients and referrals, or paid leads. The answers, taken together, paint a clear picture.
One more question worth asking, particularly for buyers: what is your actual negotiation approach when a seller won't move? Agents who have a real answer — specific tactics, specific examples — have done this work. Agents who give you a vague answer about "building rapport" probably have not done it enough times to have developed a method. The dynamics behind why some sellers leave money on the table in negotiation also illustrate, from the other side of the table, what a prepared buyer's agent should be watching for.
The simplest summary: the best Chicago real estate agent is the one who can show you the numbers, explain the strategy, communicate without prompting, and has a verifiable track record of doing exactly that for over a hundred clients before you.
Frequently Asked Questions
FAQ: How do I verify a Chicago real estate agent's transaction history?
You can ask the agent directly for their total closed transaction count and request that they walk you through recent closings. You can also check their brokerage's internal rankings if they are willing to share them, look at the volume and recency of verified Google reviews, and ask for references from clients who closed within the past six months. Awards from verified professional bodies like the Chicago Association of Realtors also provide independent confirmation of production.
FAQ: Does it matter which brokerage a Chicago agent is with?
The brokerage brand matters less than the individual agent's track record. A top-performing agent at a lesser-known brokerage will typically outperform a mediocre agent at a well-known one. What matters is how many deals the specific person in front of you has closed, how recently, and what their clients say about the experience.
FAQ: What should I look for in a real estate agent if I'm buying a condo in Chicago?
Beyond the general qualities of strong communication, local market knowledge, and negotiation experience, a good condo buyer's agent will know what questions to ask before you write an offer. Specifically, they should advise you to ask the listing agent about the building's reserve fund balance, any upcoming or past special assessments, and any known building-wide issues. Those answers can significantly affect whether a deal makes financial sense before you commit. Everything else — meeting minutes, the 22.1 disclosure, rules and bylaws — gets reviewed after you go under contract during attorney review.
FAQ: How important are Google reviews when choosing a Chicago real estate agent?
Very, as long as you read them critically. Look for volume, recency, and specificity. A pattern of 100-plus detailed, recent reviews from clients who describe concrete situations is a meaningful signal. A handful of five-star reviews with no detail tells you almost nothing. The most reliable reviews describe how the agent handled a problem, not just whether the transaction closed smoothly.