House Sitting in Grand Boulevard, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed New Years Availability
1. Daniela

Reliable & Experienced Sitter

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Daniela is the best!! I have a 60 lbs Plott Hound and left to go out of the country for three weeks during which time Daniela stayed at my house. I came home... (more)"

2. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"She's a lovely girl. It's hard to give a review, since we weren't home and left shortly after she got to our home, but we liked her very much and would defi... (more)"

3. Megan

grad student & dog lover!

Hyde Park, Chicago , IL, 60615

House Sitting, Dog Walking

1 repeat client

"Carter absolutely loved Megan! She enjoyed her company and made a new friend. We'd definitely have Megan watch Carter for us again! (more)"

4. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly went way above and beyond being a good sitter- she was fantastic! She was always prompt, friendly and professional. We received pictures and updates th... (more)"

Available this weekend
5. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

6. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Krystina was amazing. I don't think my dog missed me a bit as she seemed so loved when I got home. Krystina even gave Sophie a bath when I was gone because S... (more)"

Available this weekend
7. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

8. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"We've never had sitter stay at our apartment however wanted Hank to be able to stay within his current environment and didn't want the hassle of taking him/p... (more)"

9. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was fantastic and was my first sitter via Rover. She took a last minute job with me (same day for a 3 day long overnight) and was great! I was comfortab... (more)"

10. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Our experience with LeAnna was wonderful! She took perfect care of our dog and cat and kept us updated throughout the stay. She really listened and We are co... (more)"

11. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

12. Eliana

I am friendly, punctual, and ready!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana took good care of our dog and cat while she stayed in our home for an extended week trip. She provided timely updates when I inquired about them throu... (more)"

13. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

Confirmed Holiday Availability
14. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"We LOVE Brittany! She took care of Miko with a lot of love and care while were out on a 14 day trip. She stayed in our house, took care of Miko and our home.... (more)"

Available this weekend
15. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

16. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

17. Erin

Run And Play All Day!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Erin is an excellent sitter! She's very clearly an animal lover, and I feel completely at peace when I leave Rumi with her. (more)"

18. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

"Thank you Emily for taking care of Cali while we were gone! Emily was flexible with the hours we needed and gave us an update or two each day. We came home t... (more)"

19. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Collin loves animals. He took care of his own dog; walking, feeding, bathing, training, and playing from age 11 until he left for college. When he comes hom... (more)"

20. Grace

Excited to meet your pup!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Gracie is stellar. I own two dogs, Vito and Thurston, and a large Tegu Lizard. Each needs walking, feeding, and love. Gracie, beyond being a sweetheart, i... (more)"

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Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy house sitters for your pets--and avoid the kennel.