Best dog walkers in Sleepy Hollow

One of the most dog friendly neighborhoods in Chicago. Instantly book and meet an exceptional dog walker in Sleepy Hollow today.

  • Thoroughly-vetted

    Each walker with Wag! has been through a comprehensive screening, including a background check and competency quiz.

  • Fully insured dog walkers

    Services booked on the Wag! platform may be protected with up to $1M property damage protection.

  • Wag! Guaranteed

    400K+ Pet Caregivers with Wag! have a trusted record of experience with over 12 million pet care services, including Sitting, Walking, Boarding & Training, across 5,300+ cities in all 50 U.S. states.

Top dog walkers in Sleepy Hollow

Promoted Caregiver
Brittany A avatar

1. Brittany A

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (74)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Promoted Caregiver
Kate C avatar

2. Kate C

Wag! Expert icon
Location icon

Chicago, IL, 60653

Five stars

5 (93)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60653

Promoted Caregiver
Amanda H avatar

3. Amanda H

Wag! Expert icon
Location icon

Chicago, IL, 60607

Five stars

5 (106)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60607

Promoted Caregiver
Lucy D avatar

4. Lucy D

Wag! Expert icon
Location icon

Chicago, IL, 60651

Five stars

5 (10)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60651

Promoted Caregiver
Jen P avatar

5. Jen P

Wag! Expert icon
Location icon

Chicago, IL, 60647

Five stars

5 (62)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60647

Promoted Caregiver
Nina B avatar

6. Nina B

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

5 (441)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60605

Promoted Caregiver
Erica C avatar

7. Erica C

Wag! Expert icon
Location icon

Chicago, IL, 60661

Five stars

5 (299)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60661

Promoted Caregiver
Alexandra M avatar

8. Alexandra M

Wag! Expert icon
Location icon

Chicago, IL, 60622

Five stars

5 (114)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60622

Promoted Caregiver
Rafael A avatar

9. Rafael A

Wag! Expert icon
Location icon

Chicago, IL, 60614

Five stars

5 (352)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60614

Atenea C avatar

1. Atenea C

Wag! Expert icon
Location icon

Ann Arbor, MI, 48109

Five stars

5 (52)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Ann Arbor, MI, 48109

Cristian S avatar

2. Cristian S

Wag! Expert icon
Location icon

Chicago, IL, 60623

Five stars

5 (197)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60623

Leslie F avatar

3. Leslie F

Wag! Expert icon
Location icon

Chicago, IL, 60632

Five stars

5 (4)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60632

Marina C avatar

4. Marina C

Wag! Expert icon
Location icon

Chicago, IL, 60638

Five stars

5 (125)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60638

Olga O avatar

5. Olga O

Wag! Expert icon
Location icon

Forest View, IL, 60402

Five stars

5 (635)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Forest View, IL, 60402

Ernesto O avatar

6. Ernesto O

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (711)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Alexandra A avatar

7. Alexandra A

Wag! Expert icon
Location icon

Chicago, IL, 60623

Five stars

5 (174)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60623

NaBeela W avatar

8. NaBeela W

Wag! Expert icon
Location icon

Berwyn, IL, 60402

Five stars

5 (49)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Berwyn, IL, 60402

Jerome M avatar

9. Jerome M

Wag! Expert icon
Location icon

Chicago, IL, 60629

Five stars

4.9 (317)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60629

Estella Q avatar

10. Estella Q

Wag! Expert icon
Location icon

Chicago, IL, 60629

Five stars

5 (45)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60629

John G avatar

11. John G

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (49)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Taylor P avatar

12. Taylor P

Wag! Expert icon
Location icon

Chicago, IL, 60612

Five stars

4.9 (192)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60612

Jesica M avatar

13. Jesica M

Wag! Expert icon
Location icon

Cicero, IL, 60804

Five stars

5 (784)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Cicero, IL, 60804

Andrea V avatar

14. Andrea V

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (160)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Emma H avatar

15. Emma H

Wag! Expert icon
Location icon

Chicago, IL, 60609

Five stars

5 (74)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60609

Gabrielle J avatar

16. Gabrielle J

Wag! Expert icon
Location icon

Chicago, IL, 60607

Five stars

5 (662)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60607

Madison J avatar

17. Madison J

Wag! Expert icon
Location icon

Riverside, IL, 60546

Five stars

5 (150)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Riverside, IL, 60546

Alexander C avatar

18. Alexander C

Wag! Expert icon
Location icon

Berwyn, IL, 60402

Five stars

4.9 (58)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Berwyn, IL, 60402

Norma H avatar

19. Norma H

Wag! Expert icon
Location icon

Berwyn, IL, 60402

Five stars

5 (219)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Berwyn, IL, 60402

Rachel W avatar

20. Rachel W

Wag! Expert icon
Location icon

Lyons, IL, 60534

Five stars

5 (227)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Lyons, IL, 60534

See the full listSee the full list

Wag! Walkers know Sleepy Hollow

Sleepy Hollow is a rectangular neighborhood in the southwest suburbs of Chicago. It is bordered by the Stevenson Expressway in the North and the Chicago Park District LeClaire in the west. The industrial area of Sleepy Hollow is clustered between the train tracks and South Knox Avenue while restaurants and small businesses are primarily along South Archer Avenue and South Cicero Avenue.

Most restaurants do not offer outdoor seating in this area. Barkin’ Beauties and Fee Fee’s Dog and Cat grooming are not far, in case your dog is in need of a haircut. The proximity of Chicago Park District LeClaire means that you will find yourself walking along these beautiful paths much of the time. For more extensive natural exploration, Stickney Park has thick tree cover around ballparks and grassy fields, as well as natural shorelines around a small lake. Several regional parks in the area are also great places to explore with your dog!

What is the terrain like in Sleepy Hollow?

Homes in Sleepy Hollow tend to be one or two-story single-family homes. Front yards are intermittently fenced. There is a good grassy divider between the sidewalk and road and lots of tall trees, so this is a good neighborhood to walk your dog on a relatively loose leash or enjoy bicycling. Blocks tend to be long, straight, and flat, making them especially good for being on wheels on the wide sidewalks.

For more diverse walking, you can head across the border of Sleepy Hollow into Chicago Park District LeClaire where you can find extensive walking trails between large and lovely grassy areas. Each individual grassy field is fenced, so you can play with your dog off-leash in these fields or walk between the fields. Across the railroad tracks and river, you can find Stickney Park next to the Stickney Water Reclamation Center. This park has large forested areas around ball fields as well as a charming little lake.

How many greenways are there in Sleepy Hollow?

The Chicago Park District LeClaire shares a border with Sleepy Hollow and is a great place to enjoy some open grassy area with your dog. There are several other small regional parks around Sleepy Hollow including Archer Park which has lots of ball fields as well as lovely trails under mature tree cover. The little water playground can be a great place for your dog to be exposed to water in a fun way as long as there aren't too many children using the playground that you will disturb.

Vittum Park has a big grassy field surrounded by trails with interspersed trees which is a perfect place for you to walk with your dog on a loose leash or play a game of ball or frisbee! For more natural areas to explore, you can go to the Stickney Water Reclamation Park where there are acres of forest as well as grassy fields and a little lake with natural shorelines.

Frequently Asked Questions

How much does a dog walk cost in Sleepy Hollow, Chicago?

plus-wag-green-icon

How do I find and choose a dog walker in Sleepy Hollow, Chicago?

plus-wag-green-icon

How long does a dog walk last in Sleepy Hollow, Chicago?

plus-wag-green-icon

How to book a dog walk in Sleepy Hollow, Chicago?

plus-wag-green-icon

Is hiring a dog walker in Sleepy Hollow, Chicago safe?

plus-wag-green-icon

How to hire a dog walker in Sleepy Hollow, Chicago?

plus-wag-green-icon

How much do dog walkers charge in Sleepy Hollow, Chicago?

plus-wag-green-icon

We're America's most trusted dog walking service

Learn more in the Wag! app

Five starsFive starsFive starsFive starsFive stars

43k+ reviews

Install


© 2024 Wag Labs, Inc. All rights reserved.


© 2024 Wag Labs, Inc. All rights reserved.