Transactional Commercial Real Estate Associate

📍 Chicago, IL | Hybrid (3 days in office)

A highly regarded Chicago-based boutique law firm is seeking a mid-level Transactional Commercial Real Estate Associate to join its growing real estate practice.

This role is ideal for an associate with 3–5 years of PQE who enjoys running deals, working directly with clients, and handling sophisticated commercial matters in a lean, high-quality environment.

The work is 100% commercial and institutional in nature. There is no residential real estate
, other than rare ultra-high-net-worth one-off matters.

You will work on:

• Commercial real estate acquisitions and dispositions
• Office, retail, and industrial leasing
• Real estate finance and lending transactions
• Structuring and negotiating complex deal documents
• Running matters with increasing autonomy and limited supervision

• 3–5 years of commercial real estate transactional experience
• Big Law training (AmLaw 100 or strong regional equivalent with a recognized real estate practice)
• JD from a Top 10–14 law school (Top 20 considered with exceptional academics)
• Strong experience across core commercial real estate transactions

• Real estate finance or lending experience
• Top-of-class academics, law review, or moot court
• Proven ability to run deals independently and manage clients

• No Big Law or equivalent training
• Law school credentials clearly outside the Top 20 without standout performance

• Sophisticated institutional work without Big Law hours pressure
• Boutique platform founded by former Big Law partners
• Highly respected real estate practice with national-caliber clients
• Hybrid schedule
  : typically Tuesday–Thursday in office, Monday and Friday remote
• Lean teams, real responsibility, and direct partner access
• Clear partner track for the right attorney
• Unlimited PTO (work gets done, but no face-time culture)

• $180,000 – $200,000 base salary, depending on experience
• Generous, transparent bonus structure based on hours worked (not punitive):
• ~1,200–1,400 hours: $2,500–$10,000
• ~1,400–1,600 hours: $10,000–$20,000
• Scales upward from there
• No penalty if workflow slows

If you are a commercial real estate associate looking for top-tier work, autonomy, and a sustainable platform in Chicago
, this is a standout opportunity.