Old Town Dog Walkers
Part of the Old Town daily routine since 1999.
Old Town’s historic triangle — Victorian rowhouses, brick-paved side streets, and the shops and cafés of Wells Street — is one of Chicago’s most charming places to walk a dog.
We would know: Chicago Dog Walkers has been walking Old Town dogs since 1999, one at a time, with a walker your dog actually recognizes.
What Every Old Town Walk Includes
- A full 25 minutes, one-on-one — never a group walk
- About 20 minutes of active walking, tailored to your dog’s pace
- Fresh water, treats, and paw clean-up before we go
- A digital report card with a photo after every walk
- GPS-tracked routes, so you can see exactly where your dog went
- A harness and collar on every walk — two points of contact
- The same dedicated walker your dog knows by sight
Where We Walk in Old Town
The quiet lanes off North Avenue
Brick-paved and calm — an Old Town favorite.
Wells Street
People-watching for the dogs who love a busy sidewalk.
The edges of Lincoln Park
Just beyond the neighborhood for a longer outing.
The historic triangle
Shaded residential blocks for an easy daily loop.
Why Old Town Dog Owners Choose Us
We’re local, and we’ve been here
Founded in Chicago in 1999. Not a national app that dropped a pin on your neighborhood.
Employees, never contractors
Every walker is hand-picked, trained, and background-checked — and covered by our insurance.
The same walker every day
Your dog sees one familiar face, not whoever happened to claim the job that morning.
A grassroots company, not an app
Our walkers are hand-picked, trained, and hired with the expectation they’ll stay at least a year — which is exactly how trust gets built in a neighborhood like Old Town.
What Chicago Dog Owners Say
Denise and the entire team at Chicago Dog Walkers are simply amazing. They’ve taken the best care of my two pups over the last five years. They are reliable and they’ve gone out of their way to help me when I need a last-minute walk or dog sit.
Highly trusted. Mark the owner asked to come to my home to introduce himself when we got started. Santiago has been walking our dog and house sitting for the last 5 years. They are a great company to work with in every way.
Getting Started Is Easy
Get in touch
Send us a note or give the office a call — we answer 9 to 5, Monday through Friday.
Free consultation
Talk with our client success manager, who answers your questions and gets your dog’s profile set up. No charge.
Meet your walker
We match you with a dedicated walker you’ll meet at your first visit. Be home if you can — share your pup’s routine, show them where the leash and treats live, and let them say hello.
Or call us at 773-394-9961