Choosing the right real estate agent in Chicago is one of the most consequential decisions you will make in an expensive, fast-moving market. The difference between a skilled agent and an average one is not measured in personality — it is measured in dollars negotiated, days on market, and whether your deal closes at all. This guide walks you through the criteria that actually matter when evaluating Chicago agents in 2026, and then looks honestly at why Riley Hextell's record puts him among the city's best.
What the Best Chicago Real Estate Agents Actually Have in Common
Not all agents are created equal, and in a city as layered as Chicago — with dozens of distinct neighborhoods, a heavy condo market, co-ops, two-flats, and gut rehabs — experience and local depth separate the field quickly. Here is what to look for.
A Verifiable Transaction Track Record
Volume matters. An agent who closes 10 deals a year is working at a fundamentally different level than one who closes 50 or 100. Higher volume means more negotiating repetitions, more contract situations encountered, and stronger relationships with lenders, attorneys, and other agents. Before you hire anyone, ask directly: how many transactions did you close last year, and in which neighborhoods?
Riley Hextell has closed more than 150 transactions in under four years and was ranked number one at eXp Realty Illinois for total transactions in 2025 — the most of any agent in the state at the company. Across eXp Realty's national network of more than 80,000 agents, he ranks in the top 50 companywide. Those are not vanity metrics — they reflect a pace of work that keeps skills sharp.
Deep, Neighborhood-Level Market Knowledge
Chicago is not one market. Wicker Park, Lincoln Square, the West Loop, Hyde Park, and Beverly each behave differently. An agent who mainly works the North Shore suburbs or focuses on one or two zip codes will be slower to recognize pricing anomalies and slower to position your offer or listing correctly. Ask any agent you interview: what have you closed in my target neighborhood in the last 12 months?
For buyers looking at specific pockets of the city, neighborhood-specific due diligence is equally important. If you are considering a condo — which is a significant portion of Chicago's inventory — the right agent will know 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. Everything else, including meeting minutes, bylaws, rules, regulations, and HOA financial statements, is reviewed after you go under contract during the attorney review period. That sequencing matters, and a seasoned agent will guide you through it correctly.
Negotiation Skill That Shows in the Numbers
Strong negotiation is harder to measure than volume, but there are proxies. Ask agents for their average sale-to-list price ratio on recent transactions. Ask how many of their deals have fallen through and why. Ask how they handle multiple-offer situations, both as a buyer's agent and a listing agent. A great agent on the buy side knows how to structure terms — not just price — that make an offer more attractive. A great listing agent knows how to create competitive tension that pushes final sale prices higher.
Responsiveness and Communication Style
In a market where well-priced Chicago listings can go under contract in days, slow communication is not just inconvenient — it costs you. Ask any prospective agent how quickly they respond to calls and texts, whether they work weekends, and who covers when they are unavailable. The answer should be specific, not vague.
Reviews From Real Clients
Peer-reviewed platforms like Google give you unfiltered access to a track record of client experiences. Look at the volume of reviews, the recency, and the specificity. Generic five-star reviews with no detail are less meaningful than reviews that describe a specific situation the agent navigated well.
Riley Hextell has accumulated more than 135 five-star Google reviews in under four years of practice — a body of feedback that reflects consistent client experience across buyers, sellers, first-timers, and investors alike. The 2024 Chicago Association of Realtors Rookie of the Year award, which he earned in his first full years in the business, reinforces what those reviews suggest: a high-output, high-satisfaction practice built quickly.
Why Military Background Translates to Real Estate
Riley served in the United States Navy before entering real estate. That background tends to produce a particular kind of professional — someone who is process-oriented under pressure, accountable to timelines, and straightforward in communication. Chicago clients repeatedly mention those qualities in their reviews. In a transaction with dozens of moving parts and tight deadlines, those traits are not incidental.
How Riley Works With Buyers in 2026
For buyers, the process starts with a clear conversation about budget, timeline, and what you actually need versus what would be nice to have. Riley works across Chicago's North Side, downtown, and surrounding neighborhoods. He connects buyers with reputable lenders early, sets accurate expectations about competition in specific price ranges, and is direct about when a property is overpriced or carries red flags.
If you are buying a condo, he will walk you through asking the right questions upfront — the reserve fund balance, any upcoming or past special assessments, any known building problems — before your offer goes in. Then he will make sure your attorney has everything needed for a thorough review during the contract period.
If you are a first-time buyer navigating a complex submarket, the West Loop first-time buyer guide and the Lincoln Park first-time buyer guide offer detailed, neighborhood-specific context that can help you go into conversations better informed.
How Riley Works With Sellers in 2026
For sellers, pricing strategy is the most important decision you will make. Riley provides a detailed comparative market analysis — not a number designed to win your listing, but one grounded in what the market will actually support. He advises on preparation and staging that improves perception without unnecessary spending, and he manages the marketing, photography, and showing process to create the widest possible buyer pool.
His transaction volume gives him something less tangible but highly practical: he has seen most of the ways deals can go sideways, and he can usually spot them early. If you are weighing what a top-performing agent can actually do differently, the article on how to tell who is actually the best real estate agent in Chicago breaks down the framework in detail.
Getting in Touch
Riley works with buyers and sellers across Chicago. If you are interviewing agents or ready to get started, you can reach him at 815-545-7476, [email protected], or rileyhextell.com.
Frequently Asked Questions
FAQ: How do I verify a Chicago real estate agent's transaction history?
Ask the agent directly for their closed transaction count over the past one to three years and in which neighborhoods. You can also ask for references from recent clients in the price range or area relevant to your search. Some agents publish their production numbers publicly or on their brokerage profile.
FAQ: What should I ask a listing agent about a condo before making an offer in Chicago?
Before writing an offer, ask the listing agent about the building's reserve fund balance, whether there are any upcoming special assessments, whether there have been any past special assessments, and whether there are any known major building issues. Those answers can meaningfully affect how you price your offer and what contingencies you include. Meeting minutes, bylaws, and HOA financial documents are reviewed after you go under contract, during the attorney review period.
FAQ: How many five-star reviews should I expect from a top Chicago real estate agent?
There is no universal threshold, but an agent with 100 or more Google reviews accumulated over a few years is demonstrating consistent client satisfaction at meaningful volume. Look at recency and specificity, not just the star rating. Riley Hextell has more than 135 five-star Google reviews earned in under four years.
FAQ: Does it matter if a Chicago agent is a top producer at their specific brokerage?
Brokerage rankings can be one useful data point, but they are most meaningful when the brokerage is large enough that the ranking is competitive. Being ranked number one at eXp Realty Illinois — a brokerage with thousands of Illinois agents — and top 50 among more than 80,000 agents nationally carries real weight. At a small boutique firm, a top-producer title may reflect a smaller competitive pool.