Pet Sitting & Drop Ins In Uptown Chicago

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
Which dates do you need?
What size are your dogs (lbs)?

Search Results

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Sitter Profile Image: Kevin W.
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Sitter Profile Image: Kevin W.
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1.

Kevin W.

All pups (young & old) need care
Lake View, Chicago, IL, 60657
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
52 reviews
15 repeat clients
from
$17
per visit

Felt so comfortable with Kevin checking in on our very senior cat while we were away. Our cat liked him too!

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Sitter Profile Image: Kaitlyn K.
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Sitter Profile Image: Kaitlyn K.
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2.

Kaitlyn K.

Energetic dog walker and pet sitter
Chicago, IL, 60618
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
43 reviews
15 repeat clients
from
$24
per visit

Kaitlyn was a joy to work with! She was super communicative and took such good care of my cats while I was out of town. 10/10 hope to work with her again!

Sitter Profile Image: Joy D.
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Sitter Profile Image: Joy D.
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3.

Joy D.

Rover 101
Extra caring, loving, soft spoken
Uptown, Chicago, IL, 60640
0.2 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
183 reviews
75 repeat clients
from
$35
per visit

Super attentive to our cat babies and prompt with drop ins. Great communication and thorough. Would definitely recommend and would book again.

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Sitter Profile Image: Koemi V.
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Sitter Profile Image: Koemi V.
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4.

Koemi V.

Love bully breeds and anxious pups!
Uptown, Chicago, IL, 60640
0.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
45 reviews
22 repeat clients
from
$30
per visit

Koemi was GREAT! We needed someone to watch our dog Lucy last minute for Thanksgiving and Koemi was wonderful. She sent lots of picture and video updates and Lucy loved her. We’d love to have her watch Lucy again!!!

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Sitter Profile Image: Faith W.
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Sitter Profile Image: Faith W.
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5.

Faith W.

Rover 101
Flexible Schedule Pet Sitter!
Chicago, IL, 60640
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
110 reviews
39 repeat clients
from
$25
per visit

Faith is an AMAZING Petsitter. She was on top of communicating with me while I was out of the country. Faith took great care of Romeo and Binx! I would love for her to watch over my little loves again! ?‍⬛?

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Sitter Profile Image: Ellie Z.
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Sitter Profile Image: Ellie Z.
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6.

Ellie Z.

Rover 101
Seasoned Pet Owner & Caregiver!
Lake View, Chicago, IL, 60613
0.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
95 reviews
31 repeat clients
from
$25
per visit

Ellie is the first pet sitter I’ve had for my cat and I couldn’t be happier with how it went. Loved seeing all of the pictures and updates that Ellie sent. I’ll definitely be a returning client! Thanks, Ellie ?

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Sitter Profile Image: Maria M.
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Sitter Profile Image: Maria M.
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7.

Maria M.

Providing Tail-Waggingly Good Care
Lake View, Chicago, IL, 60613
1.2 mi. away
Drop-In Visits, Dog Walking
4 reviews
from
$20
per visit

Maria has cared for our three dogs in numerous occasions. We mainly use Maria for extended trips away. She is the most reliable caregiver we’ve ever had. She is very attentive and loving with the dogs and always follows our instructions and requests related to their needs and routines. She is the best and the dogs love her dearly.

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Sitter Profile Image: Miranda & Elise C.
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Sitter Profile Image: Miranda & Elise C.
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8.

Miranda & Elise C.

I like big mutts and I cannot lie.
Lake View, Chicago, IL, 60613
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
84 reviews
29 repeat clients
from
$30
per visit

Miranda & Elise are Rockstar sitters. It was my first time scheduling walk-ins with them, and they took such good care of my senior, large dog babies. My one pup has to take special meds and can be quite the Houdini when taking his pills. But they managed it all and even washed their food dishes. Will book again!

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Sitter Profile Image: Hallie B.
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Sitter Profile Image: Hallie B.
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9.

Hallie B.

Rover 101
Teacher by day, animal lover 24/7!
Chicago, IL, 60613
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
8 repeat clients
from
$20
per visit

Very happy we got to use Hallie’s services while out of town this weekend. She is reliable and very responsive. Can’t wait to use her services again in the future!!

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Sitter Profile Image: Kaira L.
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Sitter Profile Image: Kaira L.
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10.

Kaira L.

Animal lover since day one
Uptown, Chicago, IL, 60640
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
from
$18
per visit

I have known Kaira for a long time. She is one of the most caring people I know and loves all animals. Kaira especially loves dogs and cats. She would be an excellent person to take care of any your family pets. She is attentive, kind, trustworthy, and enjoys being around and taking care of animals. She has taken care of my family pets to include dogs, cats, tropical fish, frogs, toads, a bird, rats, dwarf hamsters, and mice over the years. I highly recommend her services to take care of any of your pet needs.

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Sitter Profile Image: Lauren K.
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Sitter Profile Image: Lauren K.
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11.

Lauren K.

I am a pet owner and adorer!
Lake View, Chicago, IL, 60613
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$20
per visit

Lauren is so great to her pets and truly loves animals. It’s so nice to see someone treat your pet like their own and that is what Lauren does. Dogs love it too, because Lauren likes to be outside and stay active and dogs are always in tow. I highly recommend Lauren to watch your pets and/or walk your dogs.

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Sitter Profile Image: Jennifer H.
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Sitter Profile Image: Jennifer H.
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12.

Jennifer H.

Rover 101
Eat. Play. Love. ❤️
Uptown, Chicago, IL, 60640
0.1 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
25 repeat clients
from
$30
per visit

My dog adores Jennifer! Whenever he sees her, he goes nuts! He really enjoys spending time with her and I feel comfortable and at ease leaving him with her when I travel. Recommended!

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Sitter Profile Image: Nadia B.
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Sitter Profile Image: Nadia B.
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13.

Nadia B.

Rover 101
Experienced, Passionate Dog Lover
Chicago, IL, 60640
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
26 reviews
6 repeat clients
from
$16
per visit

Nadia has been an excellent cat sitter for my two little dudes! She’s always very timely, attentive, and goes above and beyond. She even brought in my mail for me while I was out of town! My new go-to !!

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Sitter Profile Image: Valentina M.
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Sitter Profile Image: Valentina M.
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14.

Valentina M.

Rover 101
All pets deserve love & respect 🥹
Uptown, Chicago, IL, 60640
0.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
136 reviews
57 repeat clients
from
$22
per visit

Valentina was nothing short of amazing! I was in need of a cat sitter for 10 days on short notice and she was able to accommodate for me. She sent daily pictures, asked questions if she had any, and at times stayed a little extra to ensure their litter box was clean and that they had all the love and attention they needed. I recommend her to ANYONE in need of a sitter!

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Sitter Profile Image: Amanda K.
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Sitter Profile Image: Amanda K.
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15.

Amanda K.

Compassionate school teacher
Uptown, Chicago, IL, 60613
0.7 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
60 reviews
26 repeat clients
from
$19
per visit

Amanda is absolutely phenomenal. This is our second time booking her and she has taken care of our “zoo” of pets so well! All five animals were so well cared for and Amanda provides detailed updates everyday. Highly highly recommend!

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Sitter Profile Image: Sonya F.
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Sitter Profile Image: Sonya F.
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16.

Sonya F.

Friendly and caring animal lover!
Chicago, IL, 60640
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
11 repeat clients
from
$35
per visit

Sonya was wonderful as always. Very accommodating even though our booking was last minute. And she’s great with our cat. Highly recommended.

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Sitter Profile Image: Marcela C.
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Sitter Profile Image: Marcela C.
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17.

Marcela C.

Cat mom of Obi-Wan and Vader!
Uptown, Chicago, IL, 60626
0.1 mi. away
Boarding, House Sitting, Drop-In Visits
2 reviews
from
$20
per visit

I have never met someone who cares for pets as deeply as Marcela. Her love and compassion for animals is truly remarkable. She treats every furry friend with the utmost respect, ensuring their safety, happiness, and well-being at all times. Marcela is incredibly responsible, always going above and beyond to meet the needs of each pet in her care. If you're looking for someone who will shower your pets with love and provide them with the best care possible, Marcela is the perfect choice! 🐾❤️

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Sitter Profile Image: Mack O.
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Sitter Profile Image: Mack O.
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18.

Mack O.

Flexible schedule, I love all pets!
Uptown, Chicago, IL, 60640
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
7 repeat clients
from
$22
per visit

Mack is great! My dog is a little extra and she stayed calm and dealt with him well. We did a couple walks and extra hang time with her. She was super timely and polite too. Would recommend for sure !

Sitter Profile Image: Carllie M.
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Sitter Profile Image: Carllie M.
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19.

Carllie M.

Love humans and animals
Uptown, Chicago, IL, 60640
0.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
117 reviews
46 repeat clients
from
$25
per visit

Carllie was phenomenal for our boys while we were away for our wedding/honeymoon. It was so nice to know that they were in good hands while we were gone.

Sitter Profile Image: Ali F.
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Sitter Profile Image: Ali F.
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20.

Ali F.

Rover 101
I'll make your furry kid feel loved
Uptown, Chicago, IL, 60640
0.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
45 reviews
14 repeat clients
from
$50
per visit

Ali is super diligent and really cares about the pets. She does a great job and provides great peace of mind that I am leaving my cats in caring and able hands.

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Uptown:

Pet parents in Uptown, Chicago, IL love dog sitters on Rover.com. 10 owners have reviewed sitters in Uptown, Chicago, giving them an average rating of 4.7/5. 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 Uptown 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 Uptown, 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 Uptown 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 Uptown, 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:

Drop-In Visits