Pet Setting & Drop Ins in Bridgeport, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Ashleigh was great! She came by to meet Boba and get the leys to our apartment before hand and checked on Boba at the times she said. She also sent a bunch o... (more)"

2. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Five out of Five Stars for Penelope! Our two kids/Italian Greyhounds have very different personalities. Penelope was patient and kind with our shy little gen... (more)"

3. Mia

Best Care for Your Best Friend

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

2 repeat clients

"Mia was so wonderful to work with. This was our first time using Rover and had to find someone very last minute. Mia was quick to respond and great at commun... (more)"

Available this weekend
4. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor has taken care of my blue heeler Winston twice while I've been on trips out of the city. She followed my care instructions excellently and I came hom... (more)"

5. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"For as long as I've known her, Sidney has loved dogs, and can tell you anything and everything about them. She is kind, caring and empathic, and treats every... (more)"

Available this weekend
6. Robert

All furry friends welcome!

Near North Side, Chicago , IL, 60654

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

10 repeat clients

"Robert was amazing, and at such short notice. Pudding was walked, fed and taken care of when I had to be out of town for a quick meeting at the last minute. ... (more)"

7. Maria

I'm a professional dog whisperer :)

South Lawndale, Chicago, IL, 60623

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Maria is a phenomenal dog sitter. She specializes in presumably big dogs, always keeping her composure no matter what the situation. Dogs always feel a certa... (more)"

8. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Breana was a great cat sitter. She sent daily rover cards and made sure my cats had fresh food and water. She also played with them a bit. Definitely will bo... (more)"

9. Madison

Pup Loving Student

Loop, Mount Pleasant, SC, 29466

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Madison was great! Very communicative and sent me photo updates of my cat each day which I appreciated immensely. I would use her services again! (more)"

10. Maddi

Lifelong dog owner and lover :)

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

About: I have owned many different dogs throughout my lifetime, including a Jack Russell Terrier, a Golden Retriever, and a Lab-Hound mix. I feel comforta... (more)

11. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

12. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

13. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

14. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

15. Samantha

My friends call me a Dog Whisperer.

Near West Side, Chicago, IL, 60607

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

6 repeat clients

About: Ever since I was a child, I have had a passion for dogs and animals of all sorts. Growing up in the Philippines, my relatives found it strange to h... (more)

16. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Catherine has been an animal lover since I've known her. She volunteered at a dog rescue shelter while away at college and continues to volunteer with a Chic... (more)"

17. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

18. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Edilberto or Eddie has helped me with my cats when I used to travel he would play with them. Give them love as if they were his own. He fed them cuddled them... (more)"

19. Catherine

Animal trainer for film and TV

Loop, Chicago, IL, 60607

Dog Boarding, Drop-In Visits, Dog Walking

7 repeat clients

About: I have owned a dog walking company in LA for over 10 years and we are still going strong. I am looking forward to walking in dogs in my home town. ... (more)

20. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

8 repeat clients

"Brittany is great! Thanks for taking care of our pup ? (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

Pet parents in Bridgeport, Chicago, IL love dog sitters on Rover.com. 7,915 owners have reviewed sitters in Chicago, giving them an average rating of 4.9/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Bridgeport, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Bridgeport, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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 Bridgeport, 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: