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Lucky Leash Chicago

Dog Walking & Pet Care

Serving happy hounds in Lincoln Square, Ravenswood, and Albany Park.


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 Neighborhood Service

We Live Where We Serve

We provide pet sitting services  you can rely on in the neighborhoods between Kimball and the lake between Peterson and Belmont (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


Where do you ship?

Charm Post ships all over the world. If you can receive mail, you can receive Charm Post.

Can I track my letter?

Since I use postage stamps to send my letters, I cannot offer tracking at this time.

How long does it take for a letter to arrive?

COVID-19 UPDATE: Shipping times within the US remain at 1-3 weeks for delivery, while international shipping can take up to 8 weeks to arrive. It's safe to assume anywhere from 1-2 weeks for travel within the US and up to 3 weeks travelling internationally. We ask that you remember we are a snail mail business! As much as we would love to offer amazing speeds like Amazon's 2-day shipping, unfortunately it just isn't possible at this time.

What age is this for?

Charm Post is for all ages! Children 4-13 often click best with our imaginitive material, however, elderly folks and even young adults have fallen in love with Charm Post.

I think my letter got lost. Can you help?

Absolutely! Navigate over to "Conttact." Fill out the accompanying form and I'll fix it up for you!

What kind of "Magic" are we talking about, here?

Magic no different than what your child would experience with Disney, Fairy Tales, or make-believe. Everything is 100% child friendly and written to delight the mind.

How do I manage my subscription?

Navigate to "Account," sign in with the credentials used during sign up, click "Manage" under Charm Post Subscription. Here, you can update your billing, address, and shipping. To cancel or pause, click "Subscription Settings" in the bottom right of the page.

Be Social

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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!


Serving: Lincoln Square, Ravenswood, Albany Park, Avondale, North Park, Uptown, North Center, Roscoe Village, and Bowmanville

© 2020 by Lucky Leash.  All Rights Reserved.