Dog Boarding in Oakland, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Search Results

Calendar Recently Updated
Sitter Profile Image: Susan C.
Sitter Profile Image: Susan C.
1.
You're Dog is My Dog!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan is very loving and considerate of my pets. One of my dogs wasn’t feeling well and she went above and beyond to make him comfortable. She feels deep compas… (more)

from

$50

per night
Sitter Profile Image: E K.
Sitter Profile Image: E K.
2.
E 
Verified Background Check
Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Coming from out of town, it is difficult to trust someone with your child. I had the opportunity to meet and inspect Liz house which made us more comfortable. T… (more)

from

$40

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ashley B.
Sitter Profile Image: Ashley B.
3.
Open house for Pets
Hyde Park, Chicago, IL, 60615
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Ashley B. was phenomenal with our dogs. They came back home happy and well rested. Our tiny dog is very anxious and can be hard to deal with so we truly appreci… (more)

from

$45

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Andrew W.
Sitter Profile Image: Andrew W.
4.
Devoted Dog Sitter to Furry Friends
Bridgeport, Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Andrew is fantastic! At the very last minute my dog sitter fell through, and Andrew came to my rescue. He was available for a meet and greet and was able to wat… (more)

from

$45

per night
Calendar Recently Updated
Sitter Profile Image: Daisy C.
Sitter Profile Image: Daisy C.
5.
making inse-purr-able cat friends!
South Lawndale, Chicago, IL, 60608
Boarding

Daisy was a wonderful caretaker to our kitten! She kept us updated during his stay and was overall very easy to communicate with. Will definitely be booking aga… (more)

from

$45

per night
Sitter Profile Image: Tania B.
Sitter Profile Image: Tania B.
6.
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
Boarding

Tania took great care of Cookie and went above and beyond to keep her happy while we were gone for 10 days! She got her food, treats and even a new coat! We w… (more)

from

$38

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Andrew T.
Sitter Profile Image: Andrew T.
7.
WFH Couple, dog park nearby 🐶
Lower West Side, Chicago, IL, 60608
Boarding, Doggy Day Care

Hands down the best dog sitter we have had in Chicago. Very professional, great service, and loves animals. Honestly just laid back, easy to deal with people … (more)

from

$55

per night
Calendar Recently Updated
Sitter Profile Image: Jamie & Ritz W.
Sitter Profile Image: Jamie & Ritz W.
WFH dog parents, pet friendly home
Near South Side, Chicago, IL, 60605
Boarding, Doggy Day Care

Jamie and Ritz did such excellent an excellent job taking care of my dog Bobbi while I was traveling! They share photos frequently and provide summary of Bobbi’… (more)

from

$50

per night
Calendar Recently Updated
Sitter Profile Image: Judith R S.
Sitter Profile Image: Judith R S.
Lover of all animals😘
Bridgeport, Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Judy took amazing care of my senior dog! She was thoughtful, caring, and went the extra mile to help him stay comfy and happy during my time away. I will not he… (more)

from

$40

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Jumari H.
Sitter Profile Image: Jumari H.
10.
Ever seen a dog smile?🙃
Grand Boulevard, Chicago, IL, 60653
Boarding, Doggy Day Care, Dog Walking

Jumari was great with our energetic 2-year-old pit mix. And his puppy is sweet as well — the two became fast friends. Jumari was communicative and flexible when… (more)

from

$38

per night
Calendar Recently Updated
Sitter Profile Image: Jasmine J.
Sitter Profile Image: Jasmine J.
11.
Plenty of long walks and treats!
Bridgeport, Chicago, IL, 60609
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jasmine took fantastic care of my anxious, senior dog. She is very accommodating, experienced, kind and gentle. Her place is immaculate and neat. I received ma… (more)

from

$40

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Kathiuska R.
Sitter Profile Image: Kathiuska R.
🧡I want a 4 legged friend 🐾
Hyde Park, Chicago, IL, 60615
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Kathiuska has been a lifesaver, looking after our dog three times when we had to hit the road. She's super caring and knows how to make dogs feel loved and at h… (more)

from

$45

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Holly R.
Sitter Profile Image: Holly R.
13.
Your Dog’s WFH Bestie
Woodlawn, Chicago, IL, 60637
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Holly was amazing! Our dog absolutely loved her and her dog Parker. We appreciated how she made Pippi feel at home, and had great communication with us througho… (more)

from

$55

per night
Calendar Recently Updated
Sitter Profile Image: Monica & Calvin M.
Sitter Profile Image: Monica & Calvin M.
Your fur baby's new best friends!
Lower West Side, Chicago, IL, 60608
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Monica and Calvin were wonderful! It was our first time leaving Sully for more than a night and their care helped us to relax and enjoy our vacation. We got dai… (more)

from

$50

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Joye E.
Sitter Profile Image: Joye E.
15.
Passionate about Pets.
Near South Side, Chicago, IL, 60605
Boarding

This was my first time leaving my puppy with someone other than family and Denali enjoyed it. Joye sent me pics everyday and kept me updated about her behavior.… (more)

from

$60

per night
Calendar Recently Updated
Sitter Profile Image: Mayela E.
Sitter Profile Image: Mayela E.
16.
I’d like to be a dog in other lives
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Mayela was a wonderful dog sitter for my greyhound! She send lots of picture and was very easy to communicate with. I would not hesitate to ask her to sit my do… (more)

from

$40

per night
Calendar Recently Updated
Sitter Profile Image: Maria C.
Sitter Profile Image: Maria C.
17.
Double lot yard adores dogs
Chicago Lawn, Chicago, IL, 60629
Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Maria was awesome when we left our older dog with her for five days. She checked in lots each day with texts and photos, which really put us at ease with being … (more)

from

$40

per night
Confirmed availability: Juneteenth Weekend
Sitter Profile Image: Ashley M.
Sitter Profile Image: Ashley M.
18.
WFH, Pet Loving, Porch, Park!
Lower West Side, Chicago, IL, 60608
Boarding, Doggy Day Care

Ashley and her family were fantastic hosts to Chase! We met up beforehand and Ashley was very thoughtful making sure that Chase would be a good fit for them. We… (more)

from

$44

per night
Calendar Recently Updated
Sitter Profile Image: Ericka J.
Sitter Profile Image: Ericka J.
19.
Loving dog walker 🐶🐾
Bridgeport, Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Ericka was very flexible and understanding with our schedule and our dog loves her! (more)

from

$40

per night
Calendar Recently Updated
Sitter Profile Image: Marissa W.
Sitter Profile Image: Marissa W.
20.
Loving Mamabear
Bridgeport, Chicago, IL, 60616
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Marissa took great care of my husky! I highly recommend her! My husky loved her so much. She took lots of pictures and video to make me feel at ease. Marissa to… (more)

from

$50

per night

Pet parents turn to sitters on Rover.com when they're looking for overnight boarding for their dog. 7,915 owners have reviewed sitters in Oakland, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect dog sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average dog boarding rates to get an idea before you start a conversation with a dog sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Oakland dog sitter in seconds on Rover.com. If you're looking for dog boarding while you're away, whether it's for one night or a whole month, you can find a dog sitter in Oakland, Chicago, IL who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks and community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers for hire, and that includes offering pet boarding in Oakland.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Oakland, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including:

Dog Boarding