Even With the Tax Hike, Can you Afford to Leave Chicago?


Chicago is a city of industry, delicious food, diverse culture and taxes. If you don’t know by now, Chicago is facing another round of tax increases, especially on real estate. This may lead everyone in Chicago to think: How am I going to afford running a business here? Or even, Why should I keep my business here when the cost of living keeps rising? We empathize with the struggle of tax hikes, but the real question is: Can your business afford to leave? Here’s why, despite the tax hikes, leaving Chicago could negatively impact your business. 

Business Access

Besides the fact that Chicago has a world-class public transportation system, Chicago is also home to major companies and top talent. Groupon, Uber, Lyft, McDonalds and more have cozied up in the Windy City, and that’s great for business. The presence of established large companies nearby and convenient transportation will draw out potential new talent, making hiring a qualified employee much easier. 

Culture Access

Chicago is one of the most diverse cities in the United States. This means that Chicago residents have a multitude of options for new foods, festivals and fun across the city. The cultures of Chicago range from Polish neighborhoods, Ukrainian Village, Chinatown, and Little Italy to Uptown’s strong African roots. We also can’t forget to mention Chicago’s top-notch comedy scene at the infamous Second City, the renowned theatre scene and the gorgeous architecture. The more activities there are to do in a city, the easier it is to attract and retain employees. A major selling point of keeping your business in Chicago is that not only can your business offer them a great experience, but their physical environment can as well. 

The Cost Perspective

As we mentioned above, Chicago has just as much to offer as cities like Manhattan and San Francisco do. But how do all of these offerings break down price-wise compared to other cities? In order to make this simple, let’s use the average cost per square foot of commercial office space in three major cities. The average cost of commercial office space per square foot is $87 in New York City, $75 in Los Angeles and $37 in Chicago. This means that office space in San Francisco is nearly double the price of office space in Chicago, and Manhattan takes the cake at $50 more per square foot than Chicago. 

Furthermore, despite the property tax increases, the residential market in Chicago is still extremely affordable compared to many other major cities. Property tax hikes or not, Chicago residential real estate will still remain a bargain compared to New York City, San Francisco, Los Angeles, Boston, Washington D.C. and Seattle to name a few. This is an enormous draw to both employees and employers alike. 

Nobody enjoys a property tax increase, but when you reside in Chicago, the bang for your buck is pretty apparent. From a business, social and economical standpoint, Chicago is a place that business owners should not consider leaving. 

Yacht Networking With TAG


We just wanted to take a moment to thank everyone who was able to attend our yacht outing! The weather held up and a great time was had by all.

As mentioned when we first got on board, the purpose of these events is for the best people in my network to meet one another and explore how they can serve as a resource for each other. A rising tide lifts all boats so hopefully many wonderful connections were made. If any were missed, please don’t hesitate to ask and I will put you together.

To Mason Awtry, our sponsor, you are the best! Thank you so much for your support.

To those who were unable to attend, you were certainly missed. TAG hosts monthly lunches & breakfasts as well as quarterly events like the boat outing so let us know if you’re interested in future opportunities to rub shoulders with the best and brightest Chicago has to offer.

Guest List:

Zak Dabbas, Co Founder, Punchkick

Rob Wilson, President, The Wilson Companies

Jay Rudman, CEO, TopStep Trader

Lucas Ward, CoFounder & CTO, Kin

Grant Gochnauer, Co Founder & CTO, Vodori

Dino Gane-Palmer, CEO, PreScouter

Patrick Anderson, CEO, OXbottling

Carter Kennedy, CEO, SoloInsight

Anders Norremo, CEO, ThirdPartyTrust

Donna Salvatore, Founder & CEO, Megalytics

Adam Hirsen, Co-Founder & CEO, UpShow

Rob Topping, Founder & Managing Member, Topping Capital

Michael Reddy, President, Digital Authority Partners

Page Ciesemier, Controller, Gage Hospitality Group

Mark Reitsma, Managing Director, Heartland Angels

Sean Harper, Co Founder, Kin

Mike Perich, CEO, Sewing Supplies Division of Bernina International

Percy Haley, Partner, Black Rhino Financial

Jake Dayan, CEO & Founder, Community Tax

Graham Peck, Venture Capital Investor, Chris Sugrue

Founder & CEO, The Crowd

Codrin Arsene, CEO, Digital Authority Partner

Dean Kaliakmanis, Sr VP, Acrisure

Joe Liberty, COO, Employee Benefits Consultants

Ben Fornell, CEO, Shurpa

Nicholas Piekoszewski, COO, OXbottling

Cindy Rudman, Owner, NoteWorthy Notes

Tim Martinez, CoFounder & CEO, MPAC Healthcare

Susan Chiaramonte, President, Educred Services

Dr. Dave Rominski, President, Doctor Referral Institute

Scott Nicholson, President, KO Business Solutions

Bill Kwit, Managing Partner, O’Malley & Kwit

Morrie Elstien, CEO, Morrie Connect

Mark Meyer, Owner, E&M Strategic Development

Dan Kuhn, CTO, Aginity

John Renaldi, CEO & CoFounder, Jiobit

Greg Vrablik, President & Owner, The Presidents Forum

Chris Carlton, President & Co Founder, Liquidus Marketing

Manny Flores, President & CEO, SomerCor

Atish Doshi, President & Founder, The Black Sheep

Todd Stukenberg, President & CEO, Illinois B.I.S.

Herb Washington, CIO, Aspire Chicago

Bob Ryan, Principal, Shields Meneley Partners

Mason Awtry, CEO, Rightsize Facility

Nick Charveron, Co Founder, Community Tax

Glenn Hafner, Managing Partner, HD Investment Group

Mike Dawson, Co Founder & COO, Shurpa

Peter Wokwicz, CIO/CEO, Various Entities

Misha Shah & Andy Sajnani, COO & CEO, Think Latitude

Ted Kanellakes, Executive Director, Chicago Medical Society

Tory Cosich, Managing Partner, ProvenIT

Charlie Graff, Founder, CrossTown Fitness

Ivan Vislavskiy, CoFounder & CEO, Comrade Web Agency

Chester Singleteary, Director, Loop Capital

Executive Networking With Tenant Advisory Group


Every month, Tenant Advisory Group hosts an Executives Luncheon to provide an opportunity for Chicago business leaders to build new, meaningful connections and discuss topics relevant to running a business.

During August’s Executives Luncheon, attendees were prompted with the question: “How do you attract and retain top talent?”

Here are a few of the lessons shared in response:

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