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How We Work

24/7 Real Time Communication


With City Digs, you can do everything from the ease of your phone or laptop by always being in the loop at your home or on the go. Renters and owners can upload or text us pictures/videos to show any problem or mishap in real time at any time! Our vendors are prescreened, licensed, bonded, insured while providing free estimates and work related guarantees. If you have preferred vendors of your own, we’ll work with them too.


We seamlessly connect qualified prospective renters with your rentals in the most efficient way possible. We maximize your property’s exposure with our data driven approach. We qualify every applicant using our thorough pre-qualification and vetting system then generate a custom lease based on your specific needs while facilitating every unit turnover and move in inspections. You can always receive real time feedback, ratings and reviews both from current renters.


You will always receive a direct deposit or check per each calendar month. We always take care of handling the payments with every renter and tenant utilizing our online payment portal. Rest comfortably and start maximizing your rental income today.


Windy City Digs

River North

West Town

Tri Taylor

Digs In Demand

Lincoln Park

South Loop



  • Who We Are

    We like to create business models in which serve the consumer the best way possible while providing unmatched 24/7 customer service. We are redefining the traditional antiquated process by delivering a simple and efficient management experience everyone can trust and rely on for years to come.

  • Brand

    We are Building an Empire on a personal level one renter and owner at a time. City Digs is a Brand started by young leaders, on a mission to rescript the fragmented management industry. We believe by building technology which streamlines the process, we’ll begin to build lasting relationships with owners and all of their renters.

  • Our Mission

    City Digs is transforming the way properties are managed by creating a digitized, yet personal management system. Our revolutionary platform seeks to connect qualified renters with verified owners while overseeing all property management aspects. We are on a mission to put an end to the fragmented and antiquated rental management process once and for all.

  • Be Part
    Of Our

Our Amazing Team

City Digs is built by a passionate team of entrepreneurs specializing in engineering, design, operations, real estate, and development.

Brandon A

Lead Development

Caesar B

Lead Engineer

Kevin B

Lead Operations



  • ◈ 1-9  UNITS 5% (Minimum $100 per unit)
  • ◈ 10+  UNITS 4% (Minimum $75 per unit)

  • ◈ Free


  • ◈ Professional Onboarding
  • ◈ Tenant Screening
  • ◈ Tenant Management
  • ◈ Move Out Inspection
  • ◈ Free leasing
  • ◈ On Demand Showings
  • ◈ 24/7 Maintenance
  • ◈ Dedicated Support Team
  • ◈ Listing & Marketing
  • ◈ Move-in Inspection

Saving Owners Money, Keeping Renters Happy

  • Features

  • ◈ Tenant Placement
  • ◈ Repairs Mark Up
  • ◈ Monthly Mgmt Fee
  • Total Cost Per Year
  • Competitors

  • ◈ 50%-100% (1st month rent)
  • ◈ $750+
  • ◈ 7%-10%   (Gross Monthly Rent)
  • $3500+
  • City Digs

  • ◈ Free
  • ◈ 0$
  • ◈ 4.5% (Avg)  Gross Monthly Rent
  • $1200 Average

Contact Us

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