A Street-Level View of Chicago's Multifamily Market: Q&A with James Thompson

James Thompson is a Senior Advisor at Triton Realty Group, specializing in multifamily as well as mixed-use investment sales across Chicago, with a particular focus on the city’s Northwest Side. 

In addition to his brokerage work, James is an active multifamily owner with hands-on experience in property management and construction. This dual perspective allows him to advise clients from the standpoint of real ownership, accurately underwriting renovation costs and accounting for operational expenses that are often overlooked in transactions. 

In this Q&A, James shares insights into his core markets, advisory philosophy, and how a neighborhood-focused approach helps clients make informed, confident decisions. 

Why were you interested in a career in real estate, and what led you to Triton Realty Group? 

I was drawn to real estate growing up because of my grandfather. He was a carpenter and that self-managed apartments in Minnesota. Growing up, I heard stories about maintaining buildings, interacting with tenants, and everything else that comes with owning apartments.  

I went on to study real estate in college, where I became more interested in the investment and advisory side of the business. I was introduced to Matt Fritzshall through a friend whose brother-in-law is Matt. I spent the summer between my junior and senior year as an intern with Matt. From there, I knew that the team at Triton Realty Group was a great fit for me and I joined the team full-time immediately after graduating.  

What was your path to becoming a Senior Advisor, and what experiences early in your career most shaped how you advise clients today? 

I’m still early in my career. My path has primarily been shaped by advising clients on buying and selling investment real estate and operating on the ownership side. In 2022, I joined Harbor Property Management as the Director of Property Management. Harbor owns and manages its own apartment buildings on the North Side and in Hyde Park by the University of Chicago. I was in charge of leasing units, overseeing turnovers, handling tenant relations, and coordinating maintenance. I obtained hands-on experience on how buildings actually perform once a deal closes. 

I purchased my own investment property in Wicker Park providing further hands-on experience from a management perspective. MY boots-on-the-ground knowledge, provides my clients with cash flow expectations, pro forma rental analysis, and real time efficiencies for operations.  

In your work as a sub-market–driven advisor, how does focusing your scope on a handful of neighborhoods elevate the service you’re able to provide clients?  

I focus on a specific set of neighborhoods, which includes Belmont Cragin, Portage Park, Jefferson Park, and Norwood Park. I am a true market expert because I have honed in on learning every metric relating to my sub-markets. I’m able to understand pricing trends, buyer demand, rent dynamics, zoning considerations, and block-by-block nuances at a much deeper level. 

My focus gives my clients an enhanced multifamily investment perspective. Whether it’s accurately pricing a property, identifying off-market opportunities, or advising on where value can realistically be created, I’m able to provide insights that go beyond surface-level data. A sub-market–driven approach leads to more precise underwriting, better execution, and ultimately stronger outcomes for both buyers and sellers. 

How would you describe the multifamily market today in Belmont Cragin and Portage Park? 

Belmont Cragin and Portage Park continue to perform as steady, fundamentals-driven multifamily markets. Historically, both neighborhoods have seen consistent rent and price growth, supported by strong rental demand, relative affordability, and a high concentration of long-term owners. Over the past several years, values and rents have trended upward without the volatility seen in more speculative submarkets. 

A notable change has been increased competition from one-off buyers and local families, many of whom have been willing to pay higher prices than experienced investors in the area. This has pushed pricing higher on certain deals and, in some cases, outpaced what traditional yield-focused investors can justify. Despite that, both markets remain attractive for disciplined, long-term investors who prioritize durability, cash flow, and neighborhood stability. 

What advice would you give to someone considering their first multifamily investment? 

My initial advice is simple: do it. There’s a reason the saying exists, buy real estate and wait; don’t wait to buy real estate. The key is approaching your first deal with the right mindset and preparation. 

If you’re serious about buying your first multifamily property, start by surrounding yourself with people who have done it before—owners, operators, and advisors who can share real-world perspective. Be conservative in your underwriting and stress-test your assumptions. Ask yourself whether the deal still works if costs come in 20 percent higher and rents are 20 percent lower than expected. Finally, pay close attention to the tenant profile. For example, buildings with long-term tenants, families, or elderly tenants often require a more hands-on approach and a longer timeline to turnover, which means planning for higher holding costs.  

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James Thompson is a Senior Advisor at Triton Realty Group, specializing in multifamily investment sales across Chicago. Triton’s advisors leverage detailed underwriting, deep local market knowledge, and a hands-on advisory approach to help clients evaluate opportunities and execute transactions with confidence. 

For investors and property owners considering a multifamily acquisition, disposition, or long-term strategy on the Northwest side of Chicago, James provides practical guidance informed by both market analysis and firsthand ownership experience.

To begin a conversation, contact James at james@tritonrealtygroup.com or (952) 607-9570.