Dog Boarding in Oakland, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability: Memorial day
liyu z.
1.
Couple family pet townhouse w/ yardNear South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care, Dog Walking

We are very thankful with liyu z. Very good with my dog . nice person thanks appreciate. If we need someone in the future for sure will go back to them, I reco… (more)

from
$35
per night
Confirmed availability: Memorial day
David N.
2.
NOT JUST A PET BUT FAMILYLower West Side, Chicago, IL, 60608
Dog Boarding, Doggy Day Care

Jennifer and David were absolutely amazing in caring for our puppy Lola. Lola is only 5 months and not fully trained and Jennifer and David made sure that she h… (more)

from
$40
per night
Calendar Recently Updated
Monica & Calvin M.
Your fur baby's new best friends!Lower West Side, Chicago, IL, 60608
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

It was my first time using Rover and I was a little nervous. Monica and Calvin did an amazing job with my puppy! They provided updates all weekend and spent ple… (more)

from
$48
per night
E K.
4.
E 
Verified Background Check
Rover 101
Animal Loving FamilyGrand Boulevard, Chicago, IL, 60653
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Elizabeth was great with Frankie. Sent me daily updates and photos. She and Frankie really bonded. I am happy to have found a sitter that loves Frankie almost a… (more)

from
$25
per night
Calendar Recently Updated
Susan C.
5.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan did a really great job with my dog Buddy! Excellent communication and care. Buddy is looking forward to his next visit and so am I! (more)

from
$45
per night
Calendar Recently Updated
6.
Furry Friend Extraordinaire!Woodlawn, CHICAGO, IL, 60637
Dog Boarding, Doggy Day Care

Dionne was super friendly and down to earth! She made us comfortable from the moment we met her, and our doggy was too! She took such good care of our girl, sen… (more)

from
$35
per night
Confirmed availability: Memorial day
7.
Home Full Time-Big Fenced in SpaceBridgeport, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Randi was great and Blue really seemed to enjoy his overnight stay at her home! (more)

from
$50
per night
Calendar Recently Updated
8.
Over a decade of experience!Hyde Park, Chicago, IL, 60615
Dog Boarding, Drop-In Visits

Kyle and Ben were great! They sent an email update with a photo so we could see how it was going. They were also very responsive and flexible with the drop-off … (more)

from
$45
per night
Calendar Recently Updated
Plenty of long walks and treats!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Tuck was happy and healthy when we got him back he seemed to really like jasmine! Jasmine was great about updating me and making sure my pup was happy while I w… (more)

from
$30
per night
Calendar Recently Updated
10.
A forever dog owner and loverLoop, Chicago, IL, 60605
Dog Boarding, Drop-In Visits, Dog Walking

Reis has both watched and walked my dog Louie many times. Louie sometimes takes awhile to warm up to new people, but loved Reis immediately. Every time she came… (more)

from
$40
per night
Calendar Recently Updated
11.
Pilsen Dog Walker/Cat Sitter!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting

Anthony is SUCH a nice person, and you can tell he loves dogs. He sent plenty of photos during the stay. I will not hesitate to book with him in the future. (more)

from
$50
per night
Calendar Recently Updated
12.
Lakefront, parks, beach & dog parkHyde Park, Chicago, IL, 60615
Dog Boarding, Doggy Day Care

Janet was AMAZING with our 15 year old Fifi. Our dog is high maintenance and requires a lot of personal attention. Janet loved on her like she was her own. N… (more)

from
$50
per night
Calendar Recently Updated
13.
Cuddlers-Work From Home-ExperiencedWest Town, Chicago, IL, 60642
Dog Boarding

This was my first time booking with Casey, and she will definitely be my go-to Rover! She sent me photos throughout Mollie's stay, which are so beautiful I save… (more)

from
$45
per night
Calendar Recently Updated
14.
Dog enthusiast, trustworthy🐶Near West Side, Chicago, IL, 60607
Dog Boarding, Doggy Day Care, Dog Walking

Kayla was amazing!! She was so good with my dog, my dog loved her immediately, and she kept communication open with messages and pictures that made me feel like… (more)

from
$37
per night
Confirmed availability: Memorial day
15.
Dog/Cat Care ChicagoGrand Crossing, CHICAGO, IL, 60621
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Aaliyah was very responsive, sent photos, and overall made us super comfortable about leaving our girl Pickle with someone new. Our dog seemed well cared for an… (more)

from
$37
per night
Confirmed availability: Memorial day
16.
Work From Home, Dog Park Next Door!Near South Side, Chicago, IL, 60616
Dog Boarding, Doggy Day Care

Whitney was AWESOME and she always kept me updated. ♥️ I’ll definitely leave Lucy with her again!! Thank you ?? (more)

from
$32
per night
Calendar Recently Updated
17.
Responsible & fun loving care giverLake View, Chicago, IL, 60657
Dog Boarding, Doggy Day Care

Julie was a fantastic dog sitter. She made sure that our dog was well taken care of, and even took him out to play in the freezing cold. I highly recommend Juli… (more)

from
$46
per night
Calendar Recently Updated
18.
Dog & cat lover!West Town, Chicago, IL, 60642
Dog Boarding, Drop-In Visits, Dog Walking

Our dog, Ivy, loved staying with Abby! She kept us updated with how Ivy was doing, and a couple fun photos and videos. We couldn’t recommend Abby any more, she … (more)

from
$35
per night
Calendar Recently Updated
19.
Experienced and caring dog lover!Near North Side, Chicago, IL, 60654
Dog Boarding, Dog Walking

We have rebooked a few times and each time I feel like I am leaving Henry in his second home. Mandy is heaven sent, so loving and nurturing. The last time we bo… (more)

from
$30
per night
Confirmed availability: Memorial day
20.
I’ll run with your dog. Home FTSouth Shore, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Omg Claudia is amazing. My dog absolutely loves her. She great at keeping you in the loop with what’s going on with your pup. She sends video, pic, text etc....… (more)

from
$38
per night

Rover also offers Dog Boarding in:

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: