In-Home Pet Sitting in Chicago
Book A Meet & GreetCare That Comes To Them
Boarding means a strange building, strange smells and strange dogs. Everything here happens in your home, on your pet's routine.
Every booking starts with a free meet-and-greet at your home — you will meet the actual sitter, not a coordinator.
Eleven Years, Nine Sitters, One North Side
Winnowbrook is nine sitters covering six neighborhoods, all of them employees rather than contractors, all bonded, insured, background-checked and trained in pet first aid. We are not an app and we do not match you with whoever is nearest. You get one named sitter and one named backup, both of whom meet your pets before a single booking is taken, and most of our clients have had the same sitter for years.
- ✓Employees, not gig contractors
- ✓Bonded, insured and background-checked
- ✓One named sitter and one named backup
- ✓Pet First Aid and CPR trained
Why Staying Home Beats Boarding
For most pets, the stress of boarding is the boarding, not the separation.
The Routine Survives
Same food, same bowl, same window, same 6am wake-up. Almost everything that upsets a pet when their owner travels is the change of place, not the absence.
No Kennel Cough, No Strange Dogs
Nothing shared, nothing contagious, and no group dynamics to navigate. For anxious, reactive, elderly or unvaccinated pets, that is the whole argument.
Cats Stay Cats
Cats are territorial, not social. Moving a cat to a cattery costs a week of stress at both ends; a sitter three times a day costs nothing but the fee.
Your House Looks Lived In
Lights on, mail in, bins out, a car that moves. A pet sitter is also the reason your home does not look empty for a fortnight.
Four Steps, Then You Can Stop Thinking About It
Tell Us The Dates
Pets, dates, how many visits a day. We confirm availability and the exact price the same day — no quotes that move later.
Free Meet & Greet
Your sitter and your backup sitter come to your home, meet your pets, learn the routine and take notes on everything from the sticky lock to the cat who bolts.
Keys And The Care Plan
Keys logged into a coded safe, and a written care plan you approve: food, medication, walk times, vet details, the neighbor with the spare key.
Photos After Every Visit
A photo and a short note each time we leave — what they ate, how they seemed, anything worth telling you. Read them from a beach, or do not.
Start With A Meet & Greet
Meet the sitter who would actually be coming. Most people book the moment their cat comes out from under the bed.
What Happens While You Are Away
The same list every time, whichever sitter is on and whatever else is going on.
Fed To Your Schedule
Your food, your portions, your times — written down at the meet-and-greet and followed exactly, including the fussy-eater workaround.
Fresh Water, Clean Bowls
Replaced, not topped up. Litter scooped every visit and fully changed on longer stays.
Medication On Time
Photographed with a timestamp so you can see it happened, including the twelve-hour-apart doses that are the reason people call us.
Actual Company
Play, brushing, a lap, or just sitting quietly in the room with a nervous animal. The visit is not over when the bowl is full.
Your Home Looked After
Mail and packages in, bins out, plants watered, lights and blinds varied so the place looks lived in.
A Photo And A Note
Sent as we leave. If something is off — not eating, limping, hiding — you hear it from us first, not on your return.
The Plan You Hope Never Matters
Every care plan names your vet, a second vet for after-hours, a spending limit you set in advance, and a local contact who can get in if we cannot. Our sitters are trained in pet first aid and CPR, and if your pet needs a vet we take them, call you from the waiting room, and keep calling until we reach you. It has happened eleven times in eleven years, and every one of those owners still books with us.
- ✓Your vet and an after-hours vet, both named
- ✓A spending limit you set before you travel
- ✓Pet First Aid and CPR trained sitters
- ✓A local backup contact with access
Before You Book
How much does a pet sitter cost in Chicago?
Drop-in visits in Chicago generally run $22–$35, and overnight stays $85–$150. Ours start at $24 for a cat visit, $26 for a dog drop-in and $110 for an overnight, with no surcharge for medication or for a second pet in the same home.
How far ahead should I book?
Two weeks for ordinary trips, and as early as you can for Thanksgiving, Christmas and spring break — those fill six months out. Regular clients get first refusal on holiday dates each September.
What is your cancellation policy?
Free up to seven days before, then half the booking, and full price inside forty-eight hours. Holiday bookings are non-refundable inside three weeks, because we turn other families away to hold them.
Will it be the same sitter every time?
Yes, plus one named backup who also came to the meet-and-greet. You will never come home to find a stranger has been in your house.
My cat hides from everyone. Is it worth it?
Almost always. A hiding cat is still fed, watered, medicated and checked on in her own house, which is a far better week than a cattery. Most come out by the third or fourth visit, and we send you the photo when they do.
Can you give injections?
Yes — insulin, subcutaneous fluids, eye and ear drops, oral medication. Our sitters are trained for it, every dose is timestamped, and there is no extra charge.
Are you insured?
Bonded and insured, covering your pets, your home and your keys. Every sitter is an employee, background-checked and trained in pet first aid and CPR. We will email the certificate before you hand over a key.
How do you handle keys?
Logged into a coded safe at the office and tagged with a code, never your address. Signed in and out on every shift, and re-issued immediately if a sitter ever leaves us.
Where We Visit
Lincoln Park & Lakeview
Full coverage, seven days, with the shortest lead times.
Logan Square & Bucktown
Full coverage; overnight stays subject to sitter availability.
Roscoe Village
Full coverage, including holiday weeks booked ahead.
Andersonville
Drop-ins and cat care daily; overnights on request.
Just outside these?
Ask. If we can fit you into a round without shortening anyone else's visit, we will.
Check Your Dates
Tell us the dates and the pets. We will confirm availability and the exact price the same day.