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.

Book Your Visit TodayCall (312) 248-2903
Fully Insured & Bonded
Photo Updates Included
Trusted by 50+ Pet Families

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

Most Popular

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.

30 minutes
Recurring (≥3x/week)$22
Occasional$25
45 minutes
Recurring (≥3x/week)$31
Occasional$35
60 minutes
Recurring (≥3x/week)$40
Occasional$45

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.

30 minutes
Recurring (≥3x/week)$22
Occasional$25
45 minutes
Recurring (≥3x/week)$31
Occasional$35
60 minutes
Recurring (≥3x/week)$40
Occasional$45

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.

30-minute visit
$25
60-minute visit
$40

Additional Fees & Enhancements

Extra Pet (same household)+$5 per walk/visit
Before/After Hours & Weekends+$5 (30m) / +$10 (45-60m)
Holidays+$10 (30m) / +$20 (45-60m)
Last-minute/Same-day booking+$10
Meet & GreetAlways FREE

*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

Major Holidays Subject to 5-Day Cancellation Policy:

• New Year's Day
• Martin Luther King Jr. Day
• Presidents' Day
• Easter Sunday
• Memorial Day
• Independence Day
• Labor Day
• Columbus Day
• Halloween
• Veterans Day
• Thanksgiving Day
• Black Friday
• Christmas Eve
• Christmas Day
• New Year's Eve

*We are available for walks throughout the day, but after-hour fees apply for walks before 7am and after 7pm

🎯 Ready to Join the Wags & Whiskers Family?

Schedule your FREE Meet & Greet today and see why Chicago pet parents trust us with their furry family members!

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.

5+ Years Experience
Insured & Bonded
50+ Five-Star Reviews
Rachael Boeskool - Pet Sitter
5.0
★★★★★

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

★★★★★
5.0from 65+ reviews on Rover

Featured Reviews

★★★★★
"Thank you taking care of Sammy and we loved all the pictures. You were wonderful!"
Scott A.
October 2025
★★★★★
"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."
Morgan H.
September 2025
★★★★★
"So happy and lucky to have found Rachael!!"
Kelsey R.
September 2025
Scott A.
★★★★★

"Thank you taking care of Sammy and we loved all the pictures. You were wonderful!"

October 2025
Kelsey R.
★★★★★

"So happy and lucky to have found Rachael!!"

September 2025
Madison N.
★★★★★

"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."

September 2025
Madison C.
★★★★★

"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! :)"

September 2025
Morgan H.
★★★★★

"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."

September 2025
Rachel W.
★★★★★

"Rachael was wonderful! Took great care of our cats and sent so many good pictures! Thank you!!"

September 2025
Ken S.
★★★★★

"Rachael is amazing! She took great care of our senior dog and gave us lots of photos and feedback."

August 2025
Rachel S.
★★★★★

"She was great with my three kitties. Communicated all updates and sent plenty of pics."

August 2025
Michael H.
★★★★★

"Wonderful job caring for our cat — always sent tons of pictures. Definitely recommend!"

August 2025

Ready to Book?

Let's discuss how we can provide the best care for your furry family members

How Our Booking Process Works

1

Reach Out

Send us a message or call to discuss your pet's needs

2

Meet & Greet (optional)

We'll schedule a free consultation to meet you and your pet

3

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.

Get in Touch

Phone
(312) 248-2903
Email
info@wagsandwhiskerschi.com
Service Areas
Old Town, Lincoln Park, Lakeview, River North, Loop, Gold Coast