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 pet.

Search

More resources

A focus on safety

Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check.Learn more about RoverProtect

Loving pet sitters in your neighborhood

Search Results

Sitter Profile Image: Braeden R.
Verified Enhanced Background Check
Sitter Profile Image: Braeden R.
Verified Enhanced Background Check

1. Braeden R.

Star Sitter
Lifelong Dog Lover, Sitter, Walker!
Lake View, chicago, IL, 60613
1.0 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 4.8 stars
25 reviews
12 repeat clients
Profile image

Braeden was great! He was very consistent with his visits and left super cute photos and messages! I would definitely book him again (if I wasn’t moving) and would recommend others to do so as well!

Availability updated 6 days ago
Sitter Profile Image: Cole W.
Verified Enhanced Background Check
Sitter Profile Image: Cole W.
Verified Enhanced Background Check

2. Cole W.

Young professional who loves pets
Edgewater, Chicago, IL, 60660
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
61 reviews
22 repeat clients
Profile image

Cole was an excellent drop in sitter! I felt much more comfortable knowing my dog could get some play time and a potty break while I was out of the house.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Erin D.
Verified Enhanced Background Check
Sitter Profile Image: Erin D.
Verified Enhanced Background Check

3. Erin D.

Star Sitter
Happy and energetic walker
Lake View, Chicago, IL, 60614
1.0 mi. away
Drop-In Visits, Dog Walking
from
$12
per visit
5 out of 5.0 stars
25 reviews
9 repeat clients
Profile image

Erin dropped in to let my puppy out and did a wonderful job! Thank you Erin!

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Mike S.
Verified Enhanced Background Check
Sitter Profile Image: Mike S.
Verified Enhanced Background Check

4. Mike S.

Star Sitter
Energetic Experienced Dog Walker
Lincoln Square, CHICAGO, IL, 60625
1.3 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
148 reviews
26 repeat clients
Profile image

Mike did a great job with our golden! Our golden is super stubborn and he actually got him to walk and go potty! His communication was awesome and he also provided some pics of our cat! Will use again for sure!

Availability updated 9 days ago
Sitter Profile Image: Jenie N.
Verified Enhanced Background Check
Sitter Profile Image: Jenie N.
Verified Enhanced Background Check

5. Jenie N.

Star Sitter
Lifelong animal lover
Uptown, Chicago, IL, 60640
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
640 reviews
185 repeat clients
Profile image

I highly recommend Jenie! My cat was well taken care of while I was away. She followed all instructions and went above and beyond to make sure everything went well! I will definitely have Jenie watch my cat again in the future.

Availability updated today
Sitter Profile Image: Angelique H.
Verified Enhanced Background Check
Sitter Profile Image: Angelique H.
Verified Enhanced Background Check

6. Angelique H.

Deliverer of unlimited scritches :)
Uptown, Chicago, IL, 60613
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
29 reviews
14 repeat clients
Profile image

Angelique was amazing! She was prompt and always sent plenty of pictures so I knew how my girls were doing. My cats are usually shy with new people when I’m gone, and they even came out to visit when she was here. I would definitely recommend and book with her again!

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Kaira L.
Verified Enhanced Background Check
Sitter Profile Image: Kaira L.
Verified Enhanced Background Check

7. Kaira L.

Rover 101
Star Sitter
Full-time cat/dog sitter available
Uptown, Chicago, IL, 60640
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
173 reviews
47 repeat clients
Profile image

Kaira was an amazing drop-in sitter to our two cats! We knew we were in great hands as soon as we met her for a meet and greet, and she gave great updates and photos every day to reassure us that our fur babies weren’t missing us too much! Will definitely look to Kaira first next time we’re out of town!!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Lavinia L.
Verified Enhanced Background Check
Sitter Profile Image: Lavinia L.
Verified Enhanced Background Check

8. Lavinia L.

The cat lover is back in Chicago ❤️
Uptown, Chicago, IL, 60640
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
41 reviews
15 repeat clients
Profile image

Lavinia was incredible! Very responsive, sent a ton of pictures and took great care of my two cats while i was out of the country. Book her!!!!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jenni S.
Verified Enhanced Background Check
Sitter Profile Image: Jenni S.
Verified Enhanced Background Check

9. Jenni S.

Crazy cat lady that also loves dogs
Lake View, Chicago, IL, 60613
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
38 reviews
11 repeat clients
Profile image

Jenni is so great!! I always get thorough details about her visits and tons of details. My kitty loves her and I feel comfortable knowing she’s in good hands :)

Availability updated 11 days ago
Sitter Profile Image: Whitney W.
Verified Enhanced Background Check
Sitter Profile Image: Whitney W.
Verified Enhanced Background Check

10. Whitney W.

Star Sitter
Pets are people, too!
Edgewater, Chicago, IL, 60640
1.2 mi. away
Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
285 reviews
80 repeat clients
Profile image

She took wonderful care of our girls and was able to come for an extra visit at the last minute when our flight was delayed by several hours. We would be happy to engage her services again.

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Paulina P.
Verified Enhanced Background Check
Sitter Profile Image: Paulina P.
Verified Enhanced Background Check

11. Paulina P.

Grad Student Dog Walker/Sitter
Uptown, Chicago, IL, 60640
0.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$22
per visit
5 out of 5.0 stars
43 reviews
10 repeat clients
Profile image

Paulina was so wonderful & communicative while watching our cats! She even got my timid cat to come out for treats and pets on the first day, which is super impressive. Would definitely recommend Paulina! ❤️

Availability updated 4 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Levi C.
Verified Enhanced Background Check
Sitter Profile Image: Levi C.
Verified Enhanced Background Check

12. Levi C.

Star Sitter
Lover of pets all shapes and sizes!
Uptown, Chicago, IL, 60640
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
10 reviews
4 repeat clients
Profile image

Thank you so much for giving Mimi the time to get to know you! Mimi can be a very scared and feisty cat, but Levi was so patient and loving to her. It made me so happy to see her open up by the end of the visits! I definitely recommend Levi as a sitter, I felt so confident leaving my cat with Levi.

Availability updated 3 days ago
Sitter Profile Image: Emily J.
Verified Enhanced Background Check
Sitter Profile Image: Emily J.
Verified Enhanced Background Check

13. Emily J.

Star Sitter
Let’s make fetch happen!
Uptown, Chicago, IL, 60613
0.4 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
17 reviews
7 repeat clients

If I ever need to have someone watch my dog, Em is immediately who I go to. She took amazing care of my dog, sending lots of updates, including of pictures over the week and was always very responsive to me. Em was able to help with my dog's anxiety (and mine too) and my dog loved being able to spend time (and play non-stop) with her dog and cat. She's wonderful with dogs and my dog loved getting to have his vacation with her. I will 100% be using Em again for any time I need to have a sitter for my dog since I know he will be well taken care of.

Availability updated 11 days ago
Sitter Profile Image: Amanda K.
Verified Enhanced Background Check
Sitter Profile Image: Amanda K.
Verified Enhanced Background Check

14. Amanda K.

Star Sitter
Compassionate school teacher
Uptown, Chicago, IL, 60613
0.7 mi. away
Drop-In Visits
from
$17
per visit
5 out of 5.0 stars
121 reviews
42 repeat clients
Profile image

Amanda was amazing!! She took the best pics of our girl Millie and took great care of her. She even went so far as to check for some of our wedding packages that were in the lobby of our building and brought them upstairs for us. She was so great and we can’t wait to book with her again :)

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Veronica B.
Verified Enhanced Background Check
Sitter Profile Image: Veronica B.
Verified Enhanced Background Check

15. Veronica B.

TLC / Budget deals!
Uptown, Chicago, IL, 60640
0.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$24
per visit
5 out of 4.8 stars
45 reviews
10 repeat clients

About: BE SURE TO REQUEST DISCOUNT CODE FIRST TIME ON ROVER PET PARENTS!! ⭐️⭐️⭐️⭐️ I have loved animals all my life , ever since I was a kid and fell in love with my grandparents mini terriers , Tibby #1 and Tibby #2, and I started out 12 years ago by watching furry family members for friends and loved ones ( also a bearded dragon🥰) I pride myself in providing a safe, loving, nurturing environment. I give additional discounts to first pet parents that rebook with me —I “love to spoil the furbabies” with playtime, belly rubs and cuddles, what better way to give them the love and attention they deserve! I focus on safety first, and make sure that all furry friends have adequate food, water, playtime and nap time. They are FAMILY 🥰 MEDICATIONS- I can guve chewable and pill /powder medications /supplements ONLY! I CANNOT administer any kind of injections under the skin for dogs or cats. They are very sensitive and may sometimes experience anxiety , so unfortunately I cannot fulfill that request. THANKYOU FOR TRUSTING ME WITH YOUR PRECIOUS FURBABIES!! 😍😍😍 I’m available from 6 am to 10 pm , I can accommodate last minute pets , when given at least one to three hours notice. I will be home full time to care for and spend time with your pet as this is my sole employment! I can care for someone’s pets in my home , my home is quiet, safe , has extra blankets toys food bowls you name it I have it! My apartment is very large and roomy , with a huge rooftop dog run and play area as well as a nearby dog park ! I can care for pets at other peoples homes as well. I give additional discounts to repeat clients and first time pet parents!!

Availability updated today
Sitter Profile Image: Madison B.
Verified Enhanced Background Check
Sitter Profile Image: Madison B.
Verified Enhanced Background Check

16. Madison B.

Star Sitter
Every animal is my favorite animal!
Chicago, IL, 60613
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
18 reviews
7 repeat clients
Profile image

Madison was nothing short of excellent - warm and friendly, super easy to communicate with, and took great care of our cat while we were out of town. Everything a pet parent could hope for; I highly recommend her services!

Availability updated 6 days ago
Sitter Profile Image: Jamie G.
Verified Enhanced Background Check
Sitter Profile Image: Jamie G.
Verified Enhanced Background Check

17. Jamie G.

In home care from a guy all pets lo
Uptown, chicago, IL, 60640
0.6 mi. away
House Sitting, Drop-In Visits
from
$17
per visit
5 out of 5.0 stars
24 reviews
9 repeat clients
Profile image

Jamie was absolutely amazing! Astra loved him and enjoyed all of her lap time with him! Thanks again Jamie for giving Astra all the love and snuggles while I was away.

Availability updated 11 days ago
Sitter Profile Image: Faith W.
Verified Enhanced Background Check
Sitter Profile Image: Faith W.
Verified Enhanced Background Check

18. Faith W.

Rover 101
Star Sitter
Flexible Schedule Pet Sitter!
Uptown, Chicago, IL, 60035
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per visit
5 out of 5.0 stars
242 reviews
65 repeat clients
Profile image

First time using Rover and Faith was wonderful and very easy to coordinate!!! Thank you for a pleasant experience, Faith! Looking forward to the next visit!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Alexander K.
Verified Enhanced Background Check
Sitter Profile Image: Alexander K.
Verified Enhanced Background Check

19. Alexander K.

Ultimate Dog Sitter in Uptown
Uptown, Chicago, IL, 60640
0.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 4.9 stars
33 reviews
8 repeat clients
Profile image

lacey is obsessed with Nigel- Alex always sends the best pictures of them playing and having a good time. and he’s always available last minute which has saved me more times than I can count

Availability updated 4 months ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Triston A.
Verified Enhanced Background Check
Sitter Profile Image: Triston A.
Verified Enhanced Background Check

20. Triston A.

Call Dr. Doolittle for Luxury Care
Chicago, IL, 60640
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$19
per visit
5 out of 5.0 stars
21 reviews
7 repeat clients
Profile image

Triston is fantastic! My cat Ollie instantly fell in love with them and they became instant best friends. I was gone for 8 days and had Triston do drop on visits and I was always updated on everything Ollie. I especially loved the photos proved!! Thank you again Triston and I will be booking with you again!!

Availability updated 10 days ago

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge