Real Moments
Genuine photos from our daily walks and visits across Chicago
Professional, reliable, and loving care for your furry family members. Serving Lincoln Park, Lakeview, Old Town, Gold Coast, and surrounding neighborhoods.
Personalized pet care services designed with your pet's happiness and your peace of mind in focus
Join our recurring plan (≥3x per week) and enjoy these exclusive benefits:
Save $3-5 per walk with consistent scheduling
Guaranteed availability during peak midday hours
Same schedule = consistent routine
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.
Specialized in-home care for your cats who prefer staying in their territory. Gentle, quiet visits that respect their unique nature. Includes feeding & fresh water, litter box cleaning, gentle playtime sessions, quiet companionship, and full respect for their space and routine.
Extended in-home care for dogs who need more than a walk but less than overnight. Perfect for long workdays, puppies, seniors, or dogs recovering from surgery. Includes full companionship, walks, feeding, playtime, and plenty of couch cuddles in your home.
Overnight care with two flexible options. Choose between having a sitter stay in your home for complete routine continuity, or boarding your pup at one of our trusted walker's homes — a cozy, family-style alternative to kennels. Both options include walks, meals, and daily photo updates.
If you cancel within 24 hours of your scheduled service, we must bill for the full service.
If you cancel within 5 days of a major holiday, we must bill for the full service.
Major Holidays Subject to 5-Day Policy:
Separate policy for overnight boarding stays — different from our standard 24-hour cancellation.
After-Hour Fees: Walks before 9am and after 5pm are subject to additional fees.
Genuine photos from our daily walks and visits across Chicago
Meet the heart behind Wags & Whiskers
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.
Every member of the Wags & Whiskers team is background-checked, fully trained, and shares a genuine love for animals
Owner & Head Walker
5+ years of professional pet care experience. Insured, bonded, and passionate about giving every dog and cat the love and attention they deserve. Rachael personally oversees every client relationship and leads the walking team.
Dog Walker
A true animal lover who brings patience, reliability, and a warm smile to every walk. Tara specializes in senior dogs and high-energy breeds alike — she treats every pup like they're her own.
Dog Walker
Known for her calm, gentle approach and incredible attention to detail. Jherlene builds real bonds with every dog she walks and has a knack for earning trust with even the shyest rescues.
"Thank you taking care of Sammy and we loved all the pictures. You were wonderful!"
"Rachel was quick to respond and great communication. She stopped by my apt before to do a quick meet and greet, and it made me feel extra comfortable leaving my cats in her care."
"So happy and lucky to have found Rachael!!"
"Thank you taking care of Sammy and we loved all the pictures. You were wonderful!"
"So happy and lucky to have found Rachael!!"
"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! :)"
"Rachel was quick to respond and great communication. She stopped by my apt before to do a quick meet and greet, and it made me feel extra comfortable leaving my cats in her care."
"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!"
We treat every pet like our own. From the first meet-and-greet to the daily walks and visits, your furry family member is in loving, capable hands.
Let's discuss how we can provide the best care for your furry family members
Send us a message or call to discuss your pet's needs
We'll schedule a free consultation to meet you and your pet
Choose your schedule and we'll confirm your booking
Ready to get started? Fill out our comprehensive new client form to tell us all about your pet's needs, preferences, and schedule requirements.