Revolutionizing Chicago Real Estate: Influential Startups to Watch in 2023 is proud to take a deep dive into the innovative and growing real estate startup scene in Chicago, Illinois. The Windy City is more than crunchy deep-dish pizza and towering skyscrapers; it’s a bustling hub of rising startup companies transforming the face of real estate through technological advancements and other unique approaches. Representing various industries from residential to commercial property management, leasing to investment, and even including a dash of trend-setting electric vehicles in the mix, these startups are making critical moves and creating ripples in the U.S. real estate market.

Whether they’re simplifying the homebuying process, providing discounted lot services, automating leasing processes or reimagining the way commercial buildings are utilized, these startups are refining the way we think about real estate. Here’s a closer look at these innovative startups refreshing the real estate industry in Chicago.

These Chicago-born startups represent the future of the real estate industry, as they balance technology with human interaction to provide new solutions for tenants, homeowners, property managers, and investors. Here is a closer look at what these innovative startups are bringing to the table.

Kairos Living

Kairos Living specializes in redeveloping and digitally updating living spaces, making them more accessible and suitable for modern residents. They are innovatively blending technology with real estate management to provide an upgraded living experience.

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RealtyAds is pushing past traditional boundaries in the commercial real estate industry, with unrivalled, targeted, and consistent outreach to critical audiences. RealtyAds was founded by Keegan Kuhn and Trevor Marticke to help facilitate better transactions within the commercial real estate business.


Ruuster simplifies the homebuying process through its comprehensive platform. Co-founded by entrepreneur Brett Siegal, Ruuster is fundamentally changing how homes are bought in Chicago and beyond.

Discount Lots

Discount Lots provides real estate brokers and supply chain services, making it easier for brokers to secure deals. The startup, helmed by William Goldberg, offers affordable real estate options for brokers in the Chicago area.


BuildingHub offers an all-in-one solution for commercial real estate operators and owners. They provide a space where all real estate operations can be easily managed, offering convenience and efficiency rolled into one portal.


Ridy is a unique addition to the list, providing rental e-scooter and e-bike services. Established by Dharmateja Medasani, Ridy is offering an exciting twist to property mobility.


RUME is an investment company that focuses on real estate. The company tweaks the concept of property investment, allowing room for creative projects in the real estate field to take off.

Square One Real Estate

Square One Real Estate offer comprehensive residential buying, selling, and leasing services, making it considerably easier for Chicago residents to navigate their real estate ventures.

Engel and Volkers Chicago

Engel and Volkers Chicago is a versatile player in the real estate industry, offering property buying, selling, and rental services all under one roof.

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STYL Residential

STYL Residential offers effective property management services, allowing landlords and other property owners to maintain their properties with less hassle and time spent.

Masters Equity Partners

Masters Equity Partners is an investment service dedicated to real estate, led by entrepreneur Ranice Brown. They serve investors and property owners, pledging opportunities for greater return.

3Gs Investment Group

3Gs Investment Group is an investment agency that specializes in managing, leasing, and selling personal and commercial properties, providing an array of property-focused services.

800 Fulton

800 Fulton differentiates itself by offering office buildings rentals that include smart buildings, fitness centers, lobbies, and parking facilities, offering a comprehensive experience.

Cook Commercial Partners

Cook Commercial Partners are a team of specialized commercial real estate brokers who have the knowledge and skills to provide businesses with the best commercial properties.


ShowingHero stands out by coordinating and automating the scheduling process between property management companies and potential renters, making the leasing process more efficient.

These startups are leading the way in redefining what’s possible in the real estate industry in Chicago and beyond, proof of the thriving spirit of innovation right in the heart of the Midwest’s largest city. The future of real estate appears quite promising, thanks to these Chicago-based startups reinventing traditional sectors and introducing fresh perspectives.

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