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Lucky Leash Chicago

Dog Walking & Pet Care

Serving happy hounds from Pulaski to the lake between Peterson and Belmont.


Fun For Your Pup

Lucky Leash is dedicated to giving your dog quality exercise and mental stimulation. We'll provide the attention and exercise your pal needs.

Canine Care

Every Lucky Leash walk is one-on-one with your pup. Your dog gets the entirety of our attention during their walks.

Personalized Service

Lucky Leash provides individualized service for each of our households. We get to know you as we get to know your dog, and we make sure your unique needs are met.

Dog Walking Rates

Simple Pricing, Easy Payments


Single Dog Walks


Double Dog Walks

+ $5

Evenings & Weekends


The Best Care for Your Best Friend

The Lucky Leash Team

The team behind Lucky Leash Chicago is passionate about animal care and about contributing to our community.


Our walkers are experienced animal lovers, and are always excited to spend time with your favorite tail-wagger.


We are committed to providing professional, personal care for you and your pet.

A lot of dog walking services won't work with dogs who have anxiety, but we always have. All dogs need walks!

A Neighborhood Service

We Live Where We Serve

We provide pet sitting services  you can rely on in the neighborhoods between Pulaski and the lake west to east and between Peterson and Belmont north to south (or thereabouts!)

Pets & People Love Us

Reviews for Lucky Leash Chicago

"We truly feel our dog couldn't be in better hands. Lucky Leash is reliable, flexible, and trustworthy - and incredibly patient with our recently adopted little buddy. I really can’t recommend them enough!"

Lily  |  March 2019

Read More Reviews


Frequently Asked Questions

Learn about Lucky Leash life


How do I schedule walks?

We are happy to work with changing schedules -- we ask that you e-mail us by Sunday morning with your weekly schedule.

How does the sign up process work?

First, we'll have a quick chat to make sure we have a dog walker available who can accomodate the days/times you need walks. Once we find a walker for you, we'll schedule an in-home meet and greet so we can get to know you and your dog (no charge). Then we'll set a schedule and start strolling!

How do I make payments?

Lucky Leash will set up automatic e-check payments through our scheduling portal. Venmo is also an accepted form of payment.

What is your cancellation policy?

Walks can be cancelled by 9:00am on the day of your scheduled appointment. This is the time we usually start our routes. There will be a full charge if a cancel occurs after 9am.

Are you insured and bonded?

Yes, indeed! Proof of insurance can be provide upon request. Through insurance and bonding, Lucky Leash Chicago protects the health of your pet and the security of your home.

How long are your visits?

A standard Lucky Leash visit is 25 minutes, including 20 minutes of outside walking time!

How many dogs do you walk at a time?

Your dog's time is their time - which means we walk them one-on-one with individualized attention (unless you have two dogs; in that case, we'll walk them together).

Be Social

Follow our adventures on Instagram!

See our pack in action!

Sign Up Today

Put Your Pup on the Path to Happiness

Get started with Lucky Leash by requesting a meet-and-greet.


We'll find a time that works for you, meet you and your dog, and connect you with your walker.

Fill out the form below, and we'll be in touch soon!


Thanks for your interest in Lucky Leash! We'll be in touch ASAP.