February 2, 2026

Commercial Real Estate Financing Questions for Chicago Owners in 2026 | Monday Market Moves

Monday Market Moves | Week of February 2, 2026

Welcome to Monday Market Moves, the weekly series from Essex Capital Markets briefing you on Chicago commercial real estate capital markets. We cover key trends in CRE debt, refinancing, and capital structures to help investors and owners navigate today’s financing environment.

This Week: Commercial Real Estate Financing FAQs — What Chicago Owners Are Asking in Q1 2026

As Chicago’s commercial real estate market continues to adjust to higher-for-longer rates, shifting lender appetites, and a growing wave of loan maturities, property owners are asking more questions about timing, structure, and execution.

At Essex Capital Markets, many of today’s conversations are less about chasing the lowest rate and more about understanding options, managing risk, making informed decisions in a more selective lending environment, and matching the best lending options with our clients’ overall strategy for the asset and for their portfolio.

Below are the most common commercial real estate financing questions we’re hearing from Chicago owners and operators right now, along with high-level insights to help frame the discussion.

Short answer: not necessarily, but timing matters more than ever.

As a loan approaches maturity, lender options tend to narrow and underwriting becomes more conservative. Borrowers inside a 90-day window may face fewer structures, tighter proceeds, or higher pricing.

What we’re seeing:

This is one of the most common questions we hear, and the answer depends less on predicting rates and more on understanding risk and objectives.

While many borrowers are hopeful for future rate cuts, waiting can introduce execution risk, especially if cash flow, values, or lender sentiment shift unexpectedly.

What we’re seeing:

Underwriting standards have become more disciplined compared to prior cycles, with a strong emphasis on in-place performance rather than pro forma assumptions.

What we’re seeing:

Regional and local banks are definitely re-entering the market, but activity remains selective. Agencies continue to play a central role in multifamily financing, particularly for stabilized assets.

What we’re seeing:

  • For transactions under $5MM, Agencies are becoming much more selective.

Many borrowers refinancing today are discovering that proceeds are lower than their prior loan balances due to valuation resets and tighter underwriting.

What we’re seeing:

Bridge financing can be a useful tool, but only when paired with a realistic exit strategy and disciplined underwriting.

What we’re seeing:

Earlier engagement creates flexibility. Later engagement creates pressure.

What we’re seeing:

Despite broader market uncertainty, deals are still closing across Chicago, particularly for well-located, well-capitalized assets.

What we’re seeing:

Equity expectations have shifted, especially for refinances and transitional assets.

What we’re seeing:

The earlier the planning process begins, the more control borrowers have over outcomes.

What we’re seeing:

Conclusion

Every financing decision is unique, but the questions borrowers are asking today reflect a shared need for clarity, preparation, and realistic guidance.

In a more selective capital markets environment, informed planning and early engagement can make the difference between limited options and a successful execution.

If any of these questions sound familiar, it is often a sign that a conversation should start sooner rather than later.

 

 

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Chicago, IL 60618
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