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.

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Top dog walkers in Sleepy Hollow

Promoted Caregiver
Joel  T avatar

1. Joel T

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Chicago, IL, 60608

Five stars

5 (312)

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Chicago, IL, 60608

Promoted Caregiver
Brittany A avatar

2. Brittany A

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Chicago, IL, 60608

Five stars

5 (65)

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Chicago, IL, 60608

Promoted Caregiver
Danielle R avatar

3. Danielle R

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Bridgeview, IL, 60455

Five stars

5 (19)

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Bridgeview, IL, 60455

Promoted Caregiver
Amanda H avatar

4. Amanda H

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Chicago, IL, 60607

Five stars

5 (95)

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Chicago, IL, 60607

Promoted Caregiver
Kate C avatar

5. Kate C

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Chicago, IL, 60653

Five stars

5 (65)

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Chicago, IL, 60653

Promoted Caregiver
Jennifer P avatar

6. Jennifer P

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Chicago, IL, 60647

Five stars

5 (0)

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Chicago, IL, 60647

Promoted Caregiver
Nina B avatar

7. Nina B

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Chicago, IL, 60605

Five stars

5 (430)

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Chicago, IL, 60605

Promoted Caregiver
Ryann K avatar

8. Ryann K

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Chicago, IL, 60654

Five stars

5 (153)

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Chicago, IL, 60654

Promoted Caregiver
Samantha J avatar

9. Samantha J

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Chicago, IL, 60654

Five stars

5 (400)

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Chicago, IL, 60654

Promoted Caregiver
Cesar E avatar

10. Cesar E

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Chicago, IL, 60640

Five stars

5 (151)

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Chicago, IL, 60640

Promoted Caregiver
Addison S avatar

11. Addison S

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Chicago, IL, 60614

Five stars

5 (428)

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Chicago, IL, 60614

Promoted Caregiver
Rafael A avatar

12. Rafael A

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Chicago, IL, 60614

Five stars

5 (343)

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Chicago, IL, 60614

Promoted Caregiver
Angela O avatar

13. Angela O

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Chicago, IL, 60657

Five stars

5 (41)

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Chicago, IL, 60657

Promoted Caregiver
Alexandra M avatar

14. Alexandra M

Wag! Expert icon
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Chicago, IL, 60622

Five stars

4.8 (93)

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Chicago, IL, 60622

Atenea C avatar

1. Atenea C

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Ann Arbor, MI, 48109

Five stars

5 (29)

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Ann Arbor, MI, 48109

Miriam  U avatar

2. Miriam U

Wag! Expert icon
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Chicago, IL, 60623

Five stars

4 (3)

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Chicago, IL, 60623

Joel C avatar

3. Joel C

Wag! Expert icon
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Chicago, IL, 60632

Five stars

5 (30)

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Chicago, IL, 60632

Holly K avatar

4. Holly K

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Chicago, IL, 60629

Five stars

5 (43)

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Chicago, IL, 60629

Marina C avatar

5. Marina C

Wag! Expert icon
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Chicago, IL, 60638

Five stars

5 (123)

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Chicago, IL, 60638

Alicia N avatar

6. Alicia N

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Atlanta, GA, 30319

Five stars

5 (1)

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Atlanta, GA, 30319

Alexandra A avatar

7. Alexandra A

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Chicago, IL, 60623

Five stars

5 (147)

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Chicago, IL, 60623

NaBeela W avatar

8. NaBeela W

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Berwyn, IL, 60402

Five stars

5 (47)

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Berwyn, IL, 60402

Olga O avatar

9. Olga O

Wag! Expert icon
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Forest View, IL, 60402

Five stars

5 (590)

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Forest View, IL, 60402

Ernesto O avatar

10. Ernesto O

Wag! Expert icon
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Chicago, IL, 60608

Five stars

4.9 (590)

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Chicago, IL, 60608

Ximena A avatar

11. Ximena A

Wag! Expert icon
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Chicago, IL, 60608

Five stars

4.7 (10)

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Chicago, IL, 60608

Jesica M avatar

12. Jesica M

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Cicero, IL, 60804

Five stars

5 (774)

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Cicero, IL, 60804

Kayla J avatar

13. Kayla J

Wag! Expert icon
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Chicago, IL, 60623

Five stars

4.9 (71)

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Chicago, IL, 60623

Emma H avatar

14. Emma H

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Chicago, IL, 60609

Five stars

5 (68)

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Chicago, IL, 60609

Madison J avatar

15. Madison J

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Riverside, IL, 60546

Five stars

5 (148)

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Riverside, IL, 60546

Alexander C avatar

16. Alexander C

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Berwyn, IL, 60402

Five stars

4.9 (53)

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Berwyn, IL, 60402

Norma H avatar

17. Norma H

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Berwyn, IL, 60402

Five stars

5 (187)

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Berwyn, IL, 60402

Laura R avatar

18. Laura R

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Riverside, IL, 60546

Five stars

5 (222)

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Riverside, IL, 60546

Maribel H avatar

19. Maribel H

Wag! Expert icon
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Chicago, IL, 60608

Five stars

5 (446)

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Chicago, IL, 60608

Rachel W avatar

20. Rachel W

Wag! Expert icon
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Lyons, IL, 60534

Five stars

5 (213)

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Lyons, IL, 60534

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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.

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