Chicago's MostTrusted Dog Walkers
Professional, reliable, and loving care for your furry family members. Serving Lincoln Park, Lakeview, Old Town, Gold Coast, and surrounding neighborhoods.
Our Services and Pricing
Personalized pet care services designed with your pet's happiness and your peace of mind in focus
Why Choose Recurring Service?
Join our recurring plan (≥3x per week) and enjoy these exclusive benefits:
Lower Rates Every Week
Save $3-5 per walk with consistent scheduling
Priority Booking
Guaranteed availability during peak midday hours
Happier Pets
Same schedule = consistent routine
Dog Walking
Daily walks tailored to your dog's needs and energy level. Professional, reliable service that keeps your pup happy and healthy. Includes photo updates during walks, fresh water refill, thorough poop cleanup, and extended exercise for longer walks.
Dog Drop-in Visits
Perfect for puppies, senior dogs, or when your pup needs extra attention. Feeding, playtime, and companionship in their favorite space. Includes feeding & fresh water, potty breaks & cleanup, interactive playtime, loving companionship, medication administration if needed, and extra cuddles for longer visits.
Cat Drop-in Visits
Specialized care for your feline friends who prefer staying in their territory. Gentle, quiet visits that respect their independent nature. Includes feeding & fresh water, litter box cleaning, gentle playtime sessions, quiet companionship, window perch time, and respect for their space and routine.
Additional Fees & Enhancements
*Please note we have a 24 hour cancellation policy. If you cancel service within 24 hours (24 hours or less), we must bill for the service
*Please note we have a 5 day cancellation policy for all holidays listed below. If you cancel service within 5 days (5 days or less), we must bill for the service
*Evening hours represent after 7pm
Meet Rachael Boeskool
Hi, I'm Rachael Boeskool, the owner of Wags and Whiskers! I've always had a passion for caring for animals, and after years of looking after dogs and cats for friends, family, and neighbors, I decided to turn that love into a business.
I provide reliable, trustworthy dog walking and drop-in pet sitting services across Chicago. My goal is to give pet parents peace of mind knowing their furry family members are safe, happy, and cared for—whether that's a mid-day walk, extra playtime, or just some cuddles and attention.
I treat every pet like my own, and I pride myself on clear communication, punctuality, and making sure each pet gets the exercise, love, and care they deserve. With 5+ years experience and 50+ 5-star reviews, you can count on me to keep tails wagging and whiskers happy.
Service Areas
Proudly serving Chicago's most beloved neighborhoods with reliable pet care services
Old Town
Lincoln Park
Lakeview
Gold Coast
River North
Loop
Don't See Your Area?
We're always looking to expand our service areas. Contact us to see if we can accommodate your location!
What Pet Parents Say
Featured Reviews
"Rachael was wonderful! Took great care of our cats and sent so many good pictures! Thank you!!"
"Rachael is amazing! She took great care of our senior dog and gave us lots of photos and feedback."
"HIGHLY recommend — patient, responsible, and trustworthy with our senior dog."
"Rachael is wonderful! Very friendly, responsible, quick to respond, and my dog is already very comfortable with her. She is in very good hands with Rachael."
"Rachael was great watching my cat for the long weekend! She had great notes and sent a ton of photos from their visits, which was appreciated. Would definitely recommend! :)"
"Rachael was wonderful! Took great care of our cats and sent so many good pictures! Thank you!!"
"Rachael is amazing! She took great care of our senior dog and gave us lots of photos and feedback."
"She was great with my three kitties. Communicated all updates and sent plenty of pics."
"Wonderful job caring for our cat — always sent tons of pictures. Definitely recommend!"
"Always on time, reliable, and sends me lots of pictures. Our go-to during the week."
"Great care of our kitties — kids loved the updates and pictures every day."
"Went above what I asked to keep my cat entertained and comfortable!"
Ready to Book?
Let's discuss how we can provide the best care for your furry family members
How Our Booking Process Works
Reach Out
Send us a message or call to discuss your pet's needs
Meet & Greet (optional)
We'll schedule a free consultation to meet you and your pet
Confirm Service
Choose your schedule and we'll confirm your booking
New Client Registration
Ready to get started? Fill out our comprehensive new client form to tell us all about your pet's needs, preferences, and schedule requirements.