Demo

Transactional Attorney

Flanagan - Bilton LLC
Chicago, IL Full Time
POSTED ON 4/8/2026
AVAILABLE BEFORE 6/6/2026

Job Summary
We are seeking a highly skilled and strategic Transactional Attorney to join our national real estate tax practice. The ideal candidate will serve as a "deal architect," navigating the complex intersection of commercial real estate and sophisticated tax law. You will be responsible for structuring, negotiating, and closing high-stakes transactions while ensuring tax efficiency and regulatory compliance across multiple jurisdictions.


Core Responsibilities
Deal Structuring & Advisory: Provide strategic counsel on tax-efficient deal structures for acquisitions, dispositions, and joint ventures.


Document Drafting & Negotiation: Draft and negotiate a wide range of complex agreements, including Purchase and Sale Agreements (PSAs), commercial leases, loan documents, and partnership agreements.
Tax-Focused Due Diligence: Lead the due diligence process, with a specific focus on identifying tax liabilities, reviewing title and survey materials, and assessing environmental risks.
Tax Incentive Optimization: Collaborate with specialists to identify and secure real estate tax incentives, such as 1031 exchanges, New Markets Tax Credits (NMTC), or Low-Income Housing Tax Credits (LIHTC).


Closing Management: Oversee the entire closing process, ensuring all legal requirements are met, funds are correctly transferred, and deeds are properly recorded nationwide.
Compliance & Risk Management: Ensure all transactions comply with federal, state, and local property and tax laws.


Required Qualifications


Education: Juris Doctor (JD) from an ABA-approved law school.


Licensure: Active member in good standing of at least one State Bar.
Experience: 3–6 years of sophisticated transactional real estate experience, ideally within a large or national law firm environment.


Tax Expertise: Strong working knowledge of federal and state tax codes as they apply to real property.


Preferred Qualifications
LL.M. in Taxation or a CPA certification.
Experience with specialized financing (e.g., NMTC, CDFI lending, or affordable housing).


Essential Skills
Exceptional negotiation skills with a focus on balancing client interests and deal viability.
Strong analytical rigor and attention to detail for reviewing complex financial and legal documents.
Excellent written and verbal communication for advising high-net-worth clients and institutional investors.
Ability to manage multiple large-scale transactions simultaneously in a fast-paced environment.


Compensation

Starting Salary: 80,000

120 hours of PTO after a 90-day probation period

Typically, 17 plus paid holidays

Employee-only medical, dental, vision, and basic life premium insurance paid by the employer

3% of salary, employer 401k contribution after one year of employment

Business casual dress code with exceptions based on assigned tasks and positions

Team atmosphere

Annual reviews


The above is intended to describe the general content of and requirements for the performance of this job. It is not to be construed as an exhaustive statement of all essential functions, responsibilities, or requirements.


A pre-employment background check is required.


Salary.com Estimation for Transactional Attorney in Chicago, IL
$121,878 to $163,368
If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Transactional Attorney?

Sign up to receive alerts about other jobs on the Transactional Attorney career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$123,673 - $176,421
Income Estimation: 
$162,804 - $221,695
Employees: Get a Salary Increase
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Flanagan - Bilton LLC

  • Flanagan - Bilton LLC Chicago, IL
  • Flanagan | Bilton is seeking a Junior Accountant to provide compliance support for our Business Personal Property Tax practice. The primary function of thi... more
  • 1 Day Ago

  • Flanagan - Bilton LLC Chicago, IL
  • Primary responsibilities include daily research and support to a supervisory attorney, including maintaining and organizing the calendar, appealing propert... more
  • 4 Days Ago

  • Flanagan - Bilton LLC Chicago, IL
  • Position Overview: We are seeking a dedicated and detail-oriented Paralegal to provide essential legal and administrative support to two supervisory attorn... more
  • 5 Days Ago

  • Flanagan - Bilton LLC Chicago, IL
  • Primary responsibilities include providing daily research and support to two supervisory attorneys, including maintaining and organizing the calendar, appe... more
  • 6 Days Ago


Not the job you're looking for? Here are some other Transactional Attorney jobs in the Chicago, IL area that may be a better fit.

  • CyberCoders Chicago, IL
  • Transactional Attorney We are a dynamic Chicago-based law firm, is seeking an experienced Transactional Attorney to join our team. We are looking for a mot... more
  • 2 Months Ago

  • BCG Attorney Search Chicago, IL
  • Job ID: 414317 Practice area:- Intellectual Property - General,Intellectual Property - Trademark/Copyright - Transaction Mid-Level Corporate Transactional ... more
  • 3 Days Ago

AI Assistant is available now!

Feel free to start your new journey!