For Chicago, IL landlords and property managers
Your Chicago rentals, covered at 2am
Managing rentals in Chicago shouldn't mean being on call at 2am. RentShepherd takes the front line — tenant calls and texts answered instantly, repairs triaged, rent tracked and auto-collected — across classic two-flats and three-flats, dense lakefront apartment corridors, and student rentals around Hyde Park and Rogers Park, while every real decision still waits for your one-tap approval.
The Chicago rental market, minus the after-hours part
From Lakeview to Logan Square to Wicker Park, renting in Chicago means classic two-flats and three-flats, dense lakefront apartment corridors, and student rentals around Hyde Park and Rogers Park. Those tenants text at midnight, report leaks with one blurry photo, and expect paying rent to be as easy as everything else on their phone. RentShepherd gives every one of them an instant, competent answer — and gives you a searchable log of every word.
Because RentShepherd is a cloud platform, it covers every Chicago zip code from day one — no local office needed, none claimed. Add your units, tenants, lease dates, and your own trusted Chicago vendors; share the number with tenants; the front line is live. Every dispatch and renewal offer still waits for your one-tap approval.
Features
The features Chicago landlords lean on most
From the first tenant text to the monthly report — here's what RentShepherd takes off your plate in Chicago.
Tenant calls and texts, covered around the clock
Tenants across Chicago message or call one number and always get a real reply in seconds — questions answered, requests logged, urgency assessed. Calls are answered by a calm voice and transcribed into the same inbox, so you read the thread on your schedule, not theirs.
Repair triage that knows a real emergency
A no-heat call on a Chicago winter night is treated as the emergency it is. Genuine emergencies escalate to you immediately, with safety guidance already sent to the tenant. Everything else is logged, prioritized, and scheduled for a reasonable hour.
Renewals prepped months ahead
Every lease in your Chicago portfolio sits on a renewal timeline. RentShepherd drafts the outreach at 90, 60, and 30 days out; you approve, edit, or hold each message with one tap.
A monthly report per property
Rent collected, repairs opened and resolved, upcoming lease dates, every conversation summarized — one clean page per property per month. Chicago property managers can hand them straight to their owners.
Your whole Chicago portfolio on one screen
Whether you hold one Chicago rental or manage whole buildings, everything lives on a single secured screen: tenants, threads, work orders, payments, leases. No spreadsheet stitching required.
Pricing that beats the traditional 8–10% cut
Pick the plan that fits your Chicago portfolio today and change it as you grow. All plans start with a 14-day free trial, no card required.
- Starter — up to 3 units$29/mo
- Growth — up to 12 units Most popular$79/mo
- Portfolio — up to 30 units$149/mo
- Enterprise — unlimited units for property management companies and large portfoliosCustom
Running more than 30 units, or managing buildings for clients? Enterprise adds per-building routing, team seats, and replies under your company's name — pricing built around your portfolio.
Ready when your Chicago phone rings next
Start the 14-day free trial: connect your Chicago units, share one number with tenants, and let RentShepherd take the front line — you keep one-tap control.