Pet Setting & Drop Ins in Armour Square, Chicago

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

Calendar Recently Updated
1. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Though it was for a short period of time we felt very comfortable leaving her with our puppy. The pictures she sent reassured us that our baby was doing just... (more)"

Calendar Recently Updated
2. Vic

I'LL TREAT YOUR DOG LIKE ROYALTY

Near North Side, Chicago, IL, 60610

Drop-In Visits, Dog Walking

"Vic has been a life-saver! Due to my suddenly hectic work schedule a year ago, I was in desperate need of someone exceptional who I could trust to walk my p... (more)"

3. Shannon

Positive and energetic dog lover!

Near North Side, Chicago, IL, 60610

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

"Shannon was so nice and had no trouble with Charlie! I received photos and received a map of their walk route. I definitely hope she can sit for Charlie ag... (more)"

Calendar Recently Updated
4. Silvia

Loving and Experienced Dog Sitter

Near North Side, Chicago, IL, 60610

Drop-In Visits, Doggy Day Care, Dog Walking

About: I am a pet owner and animal lover! I have over 15 years experience caring for dogs, cats, birds, and fish. I have worked with many animals and am v... (more)

5. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

Calendar Recently Updated
6. Jennifer

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Such an AMAZING job! Jennifer really saved me with my last minute booking, and was wonderful with my cute little cocker spaniel. She gave him walks and even ... (more)"

Calendar Recently Updated
7. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"This is the second time Payal cat sits for us! she is lovely with the kitties, communicative and very thoughtful. She checked in on them twice somedays and e... (more)"

Calendar Recently Updated
8. Ariel

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel is wonderful with my dog! I have a 70 pound pit mix that likes to pull and, while she looks tiny, she manages to control and hold onto Kobe quite easil... (more)"

Calendar Recently Updated
9. Chenika

Fun & Passionate Sitter!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits

"Chenika took care of our two cats this past weekend. At our initial visit she was very friendly and made us feel very comfortable about leaving our cats in h... (more)"

10. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"Eddie always does a great job with our dogs. He’s sensitive to their unique needs and any questions or concerns we have. (more)"

Calendar Recently Updated
11. Megan

Last minute bookings available!

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Megan did such a great job. I had to leave without getting to go home to check on my cats and Megan figured everything out easily and made it stress free. Sh... (more)"

Calendar Recently Updated
12. Maggie

Dog lover & long walk enthusiast

Near West Side, Chicago, IL, 60661

House Sitting, Drop-In Visits, Dog Walking

"Maggie did some drop ins with my cat Angus. I could tell from the pictures he was having fun playing and was so happy she didn’t time with him! (more)"

Calendar Recently Updated
13. Katja

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

About: I have cared for dogs my entire life working as a foster parent for multiple organizations including Eye on the Sparrow and AARF. Currently, I have... (more)

14. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"I am so happy I found Crystal. It is my second time hiring her to check in on my bunny when I was out of town and she does an exceptional job and I definitel... (more)"

Calendar Recently Updated
15. Olivia

I’ll run with your dog.

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Olivia was very reliable and always on time to walk my dogs. I knew I could always count on her! She was also very loving to my dogs always spending time pet... (more)"

16. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

"Enoch is amazing, as always. Not only did he help care for my creatures, but he help with getting ride of my not so nice neighbor, a RAT!!!! Enoch is observ... (more)"

Calendar Recently Updated
17. David

Caring for other's dogs since 1990

Bridgeport, CHICAGO, IL, 60608

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

"David is the best dog caregiver ever! My dog, who can be a bit fearful of new people, got along with David right away. He is always calm, friendly, and profe... (more)"

18. Sarah-Bruce

Loves trying diverse walking routes

Armour Square, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Sarah-Bruce has a deep appreciation for dogs of all sorts. She is very responsible and caring when it comes to handling them. My dogs Rocco and Maria love he... (more)"

Calendar Recently Updated
19. Sam

Borderline Raised by Dogs.

Bridgeport, CHICAGO, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Sam is a great guy! Super charismatic, energetic, talkative, and responsible. He's great with dogs and is very attentive to the needs of people and animals a... (more)"

Calendar Recently Updated
20. Alison

Who let the dogs out? Me.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Alison was great with Zues. She made sure to send pictures to keep me up to date while I was away. Got back a happy and safe puppy, definitely recommend goin... (more)"

Pet parents in Armour Square, 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.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Armour Square 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 pet sitters in Armour Square, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 Armour Square pet sitters and avoid the kennel.

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 Armour Square, 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: