Our Team

Jack Brennan

Western Suburban Lead | Broker

Jack is responsible for selling over $40 million (YTD by volume 2020-2021) totaling over 50 transactions across Chicago and its western suburbs. Raised in Hinsdale and residing in Fulton Market, Jack brings fresh energy, unique perspective, deep knowledge, and an unwavering work ethic to city and suburban real estate.

Commuting daily between the city and the western suburbs—Jack adds a new dimension to his portfolio. Jack's unmatched understanding of the suburban marketplace, paired with his love and appreciation for city living offers an effortless transition between city and suburbs. Whether it's wanting to know schools, parks, Saturday night dinner spots or Sunday morning brunch, Jack is your answer.

Jack operates to get the results he wants by taking pride in the journey—no detail, deal, or dollar is unimportant. His high-touch personality, attention to detail, commitment to communication, and ability to thrive in a fast-paced environment and keep you looped in every step of the way, makes his service incomparable to his competitors. His unrivaled approach paired with the abilities and offerings of Compass makes Jack your guy. 

Jack’s external involvements include Trustee for The Community House (youngest named Trustee in its 80 year history).

Eli Masud and his team are great! The entire transaction was handled with professionalism and clear, prompt communication. Eli took all of the anxiety out of the hom...
Brian King
Eli at Second City Agents is the best in the biz! Communication is A+, attention to detail and overall knowledge is A+ and feeling like you are in good hands A+. Wil...
Bobby Koertgen
Eli and Sal were wonderful to work with. They were very transparent which we needed as first time buyers. We had tons of questions that they were able to answer. It...
Maggie Wall
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Every team member has deep roots in their local neighborhood, bring specialized business skills to the table, and has a hardworking mentality coming from a competitive athlete background. Make Second City Agents YOUR First Choice!
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