Dog Services

We happily serve these Chicago neighborhoods:

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

dog walking

GPS used for every walk. Clients will have a territory-specific team of walkers. Daily walkers will rotate among this team. ***Minimum of three walks per week.

Premier Walk with On-Leash Etiquette Specialist
One 30-minute session – $50

Daytime Monday-Friday, (9:30 am through 3:30 pm*)
40 minute walk  – $25
25 minute walk – $18
15 minute walk  – $13.50
Puppy walks (two 15-minute daytime walks) – $27.50

*All times listed are the start of a two-hour interval, i.e. 9:30am-11:30am or 5:00pm-7:00pm

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)

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





pet sitting

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.

Overnight Pet Sitting
Our reliable and competent sitters will stay overnight with 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 4 walks per day on their usual schedule, feedings, some much-needed socialization, and playtime. $75/day

Non-Overnight Pet Sitting
If an overnight stay is not necessary, we can come walk your pup and feed them as many times as you specify. Price varies based upon walk schedule. Inquire our pricing.

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. $30/hour

Holiday Pet Sitting
Base rate doubles –$150/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.

Cat and Rabbit Sitting
These services are perfect for those cat and rabbit owners looking for care during trips! Instead of boarding your pet, our sitters will come to your home, feed and water your pet, clean out the litter box, and provide socialization and play opportunities depending on your pet’s desires. $17/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.  $10/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 – $30

Round-trip transportation
Round-trip transportation – $50/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!


DDI knows that our clients have busy lives and that it can be difficult to provide their beloved pups with adequate training. We have an in-house dog trainer, Mike Hippensteel, to assist in your training efforts.

Mike is a Fetchfind Academy graduate and specializes in cynopraxic training. Cynopraxic training promotes cognitive, emotional, and behavioral changes by utilizing positive reinforcement training techniques.

DDI offers group training sessions focused on basic obedience skills, private training sessions focused on behavioral issues and mini leash etiquette sessions. Mike also joins DDI walkers on weekly walk alongs to ensure consistent leash etiquette usage and to assist with any walking issues.


  • 1 private training session: $90
  • 4 private training sessions: $340
  • 8 private training sessions: $635
  • Mini leash etiquette session: $50
  • Group training events: $50