What neighborhoods does Tails Up Chicago serve?

We serve the following neighborhoods in and around downtown Chicago: South Loop, West Loop, Wicker Park, Bucktown, River North, Gold Coast, Old Town, Lincoln Park, Lakeview.


How does the sign-up process work?

Fill out a contact form on our website. A representative from Tails Up Chicago will reach out to you within 24 hours of when your request is submitted. Our representative will take down additional information (home address, desired walking schedule, etc..) and schedule a “meet and greet” with you and your dog.


What is a “Meet and Greet”? 

A “meet and greet” is a visit with the owner of Tails Up Chicago -- Liz Rodriguez. Liz will meet both you and your pet and answer any questions you might have. Liz will take down important information about your pet (vet information, medication information, feeding schedule, etc..). Liz will provide you with information about our walkers and which of our walkers will be walking your dog. If desired, you can schedule an in-person meeting with our walker before walking begins. Liz will also provide you with a barcode as our walkers will scan this at the beginning/end of each visit. 


What is your cancellation policy?

A full refund will be provided if a cancellation takes place before 24 hours of visit. A $10 fee will be charged if a cancellation takes place between 24 and 3 hours of a visit. No refund will be provided if a cancellation takes place less than 3 hours of a visit.


How do I schedule walks?

You can schedule walks by email or through your online account. We ask that you schedule a walk at least 24 hours before it is set to take place. We recommend scheduling recurring weekly walks at the same time each day to help with the scheduling process. We will be as flexible as we can be, however.


Will we have the same walker each day? What happens if our walker is unavailable?

Yes. We will do our best to make sure you have the same walker each day, however there will be a $4 additional charge for all services booked the day of. If your walker is unavailable for whatever reason, we will find a replacement walker so your pet still gets their daily walk/attention. Liz will discuss backup walker options during your “meet and greet”.


Is there a minimum number of walks required per week?

No. You can schedule as few or as many walks per week as you like.


I scheduled a 10:00am walk -- when exactly will my walker arrive?

Our service windows are two hours wide. If you schedule a 10am walk, our walker will arrive sometime between 9am and 11am. If an exact time is required, we will do our best to accommodate such requests.


Are your walkers background checked?

Yes. All of our workers are trained, certified, and background checked. 


Do you monitor your walkers?

Yes. We continuously monitor our walkers to make sure they are providing the best care for your pet.


Do you provide references?

Yes. Also, our “Doggie Tales” page sets out testimonials we have received.


Do you allow dogs to be off leash?

No! Tails Up Chicago has a strict no LEASH OFF policy.



No, Tails Up Chicago walkers will not take a dog to a dog park during a walking service.


How do I make payments? 

We accept cash, checks, and the following credit cards: Visa, Mastercard, and Discover Cards. For customers paying by credit card, we process payment at the end of each week on the credit card we have on file for a customer. Payments are processed through the software system PetCheck.


Will your walkers administer medication?

Yes. Our walkers are able to administer medication at the request/instruction of an owner. Our walkers will NOT administer insulin or any other medication which involves an injection.


Are you insured? What does your insurance cover?    

Yes. We are insured through Pet Sitter Associates. Our insurance covers damage to your personal property up to $100,000. All other claims are insured up to $1,000,000 with a $2,000,000 aggregate.


What is Puppy Time?

Puppy Time is a proprietary system for puppies developed by Tails Up Chicago. The system aids in potty training your puppy and consists of multiple 15 minute walks per day.


Why choose Tails Up Chicago?

When choosing a dog walking and pet sitting service, it is important to choose a company you can trust. As explained above, we have an extensive walker vetting and training process. We want to make sure your pets are always in the best hands and receiving the best treatment. 

It is also important to know that your pets are receiving the attention/service you have purchased. As an owner, you will automatically receive an email when our walker arrives as well as when our walker leaves. The automatic arrival email is triggered once our walker scans the barcode upon arrival. The automatic departure email is triggered once our walker scans the barcode at the end of service. The departure email will include the following information:

  • The duration of the walk.

  • A map showing the walk route. View details on GPS tracking here>>

  • Whether or not your dog went to the bathroom.

  • A picture(s) of your dog during the walk.

  • Any comments (when necessary) from the walk.