Dog Services

We happily serve these Chicago neighborhoods:

Lake View, Lincoln Park, Roscoe Village, Lincoln Square, Logan Square, Bucktown, Wicker Park, River North, West Town, Old Town, North Center and River West.

dog walking

We offer services 365 days a year! GPS used for every walk as well as real-time updates and walk pictures.

WEEKLY DOG WALKING PACKAGES: Daytime Monday-Friday, (9:30 am through 3:30 pm*)

Package Details

Packages require that you have at least 3 recurring daytime appointments per week.  

  • $22 (15 min)
  • $28 (25 min)
  • $36 (40 min)
  • Two 25-minute walks/day: $29/walk
  • Two puppy 15-minute walks: $23/walk (1- hour interval)

**40 minute walks are not available regularly during peak intervals between 11am-1pm**

As-needed Scheduling

No walk minimum. Service requests must be submitted by 5 p.m. the day before. For walks on Monday, requests need to be submitted the previous Friday by 7:45 a.m.

  • $26 (15 min)
  • $33 (25 min)
  • $42.50 (40 min)

Evenings, Mornings, Weekends & Holidays
An additional $6 per walk for the following:

  • Weekday mornings (8:00am through 9:00am*)
  • Weekday evenings (4:30pm through 8:30pm*)
  • Weekends (Friday 4:30pm through 8:30pm*, Sat/Sun 8:00am through 8:30pm*)

*All times listed are the start of a two-hour interval, i.e. 8:00am-10:00am or 8:30pm-10:30pm

Multiple Dogs
An additional $5 charge added per dog. For the safety of our walkers and instruction of our dogs, we will walk NO MORE than 2 dogs per client.

Rescue Clients
First three walks are free! (Six months minimum)

Plant Service                                                             

$14 for daily plant watering service

If an emergency occurs, we use:
Chicago Veterinary Emergency Services
3123 N. Clybourn, Chicago, IL 60618


Photo cred: Poodles 2 Poodles

puppy visits

Our customizable puppy services are designed to provide your young puppy with exercise, potty time, feeding and/or playtime depending on what your young pup needs!

We offer a 1-hour preferred arrival window for all puppies under 6 months of age. We can bring your puppy outside for the entire walk time or you can customize your visit time to be part potty time and part indoor playtime or feeding. We recommend twice a day puppy walks to ensure a good potty training routine is established for your young pup! Our daytime puppy services are eligible for our frequency discount pricing as well!

  • 15 minute puppy walks start at $23 per walk
  • 25 minute puppy walks start at $29 per walk

pet sitting

***Contact us for details on our petsit and booking policies. 

We know how important it is to have your dog in a safe and comfortable setting while you are away on vacation or on business.

We realize that sending your dog to a daycare or boarding facility may not always be an option, so we have services to make your time away from your pooch as pleasant an experience as possible.

Pet Sitting
Our reliable and competent sitters will care for your dog where he/she is most comfortable—your home. Your dog will have everything he/she is familiar with while also enjoying up to 3 walks per day on their usual schedule, feedings, some much-needed socialization, and playtime. $135/day

Hourly Pet Sitting
If you only need care for a few hours we can book one of our sitters to come over and sit your pup. This includes a sitter’s attention for the entire duration of the reservation. $40/hour

Holiday Pet Sitting
$180/day. One month advanced cancellation notice required otherwise 50% forfeiture of petsit fees.

Additional Dogs
For any additional dogs present at a petsit, a flat $8/day is added to the charge.

Critter Sitting
These services are perfect for rabbit, lizard or other domestic pet owners looking for care during trips! Instead of boarding your pet, our sitters will come to your home, feed and water your pet and provide socialization and play opportunities depending on your pet’s desires. $26.50/day

Fish Visits
If you’re going away for the weekend but your fish still need to be fed, DDI is here to help you out! We’ll stop by to feed your fish each day according to your tank’s needs.  $16/visit


pet taxi

Our custom pet taxi service provides transportation to and from vet appointments, groomers, doggy day care, trainers, and more.

We offer a reliable service to help you with your busy lives! A DDI employee will pick up your dog at either a designated time, or time interval, and will transport him/her to important appointments. We can accompany your dog during the appointments or can simply transport them to and from. Our service is totally customizable. Day and time restrictions apply.

One-way Transportation
One-way transportation to desired location at exact time – $35

Round-trip transportation
Round-trip transportation – $55/hour.  If pet is accompanied during appointment, charge of $10 for every 20-minutes is applied.

Additional charges apply when time overage occurs.


pet photography

Dogs Deserve It offers custom pet photography with Christy Gregory.

Choose from individual, holiday themed or family shots all in the comfort of DDI’s offices. Each photo session includes one hour of photo time, all images edited on a disk and a choice of which images to retouch. $100/60-minute session


field trips

DDI dogs get to explore the city with our monthly field trips!

From cruising along the lakefront to sampling some of the city’s best dog treats, we provide half day excursions designed to entertain your dog! Costs range anywhere from $50-75 and include transportation.

Dogs have to be dog-friendly. Field trips are first come, first serve.


wedding escorts

We offer premier services to assist with weddings!

We will take care of all the things your canine companion needs so that you and your guests can enjoy your special day.

We will pick up your dog from home, put on any wedding attire, and ensure they are occupied and cared for during the ceremony and/or photo shoot. Once they have completed their portion of your special day, we will take them back home or to the boarding facility you have arranged for them.

Our detail-oriented staff will be your pup’s chaperone and caregiver during your event. Service starts at $80/hour.

Ask about our small selection of dog attire. We might have the perfect outfit for your pup!