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

1. Oscar C

Chicago, IL, 60629

Five stars

5 (51)

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Chicago, IL, 60629

2. Jen P

Chicago, IL, 60647

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5 (451)

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Chicago, IL, 60647

3. Mary C

Chicago, IL, 60642

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5 (54)

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Chicago, IL, 60642

4. Adriannah S

Chicago, IL, 60601

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5 (112)

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Chicago, IL, 60601

5. Colleen B

Chicago, IL, 60610

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5 (90)

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Chicago, IL, 60610

6. Madeleine B

Burr Ridge, IL, 60527

Five stars

5 (225)

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Burr Ridge, IL, 60527

7. Anna F

Chicago, IL, 60614

Five stars

5 (96)

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Chicago, IL, 60614

8. Morgan M

Chicago, IL, 60614

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5 (33)

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Chicago, IL, 60614

9. Parker D

Chicago, IL, 60618

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5 (35)

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Chicago, IL, 60618

10. Siara C

Chicago, IL, 60657

Five stars

5 (49)

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Chicago, IL, 60657

1. Atenea C

Ann Arbor, MI, 48109

Five stars

5 (125)

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Ann Arbor, MI, 48109

2. Cristian S

Chicago, IL, 60623

Five stars

5 (297)

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Chicago, IL, 60623

3. Janet M

Chicago, IL, 60623

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5 (30)

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Chicago, IL, 60623

4. Holly K

Chicago, IL, 60629

Five stars

5 (55)

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Chicago, IL, 60629

5. Olga O

Forest View, IL, 60402

Five stars

5 (861)

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Forest View, IL, 60402

6. Ernesto O

Chicago, IL, 60608

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5 (951)

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Chicago, IL, 60608

7. Alexandra A

Chicago, IL, 60623

Five stars

5 (210)

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Chicago, IL, 60623

8. Jerome M

Chicago, IL, 60629

Five stars

4.9 (321)

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Chicago, IL, 60629

9. Brianda C

Chicago, IL, 60629

Five stars

5 (1)

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Chicago, IL, 60629

10. Marlene G

Cicero, IL, 60804

Five stars

5 (61)

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Cicero, IL, 60804

11. Erin C

Oak Park, IL, 60304

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5 (50)

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Oak Park, IL, 60304

12. Andrea P

Chicago, IL, 60608

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5 (127)

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Chicago, IL, 60608

13. John G

Chicago, IL, 60608

Five stars

5 (156)

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Chicago, IL, 60608

14. Citlali S

Berwyn, IL, 60402

Five stars

5 (22)

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Berwyn, IL, 60402

15. Jesica M

Cicero, IL, 60804

Five stars

5 (810)

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Cicero, IL, 60804

16. Claire B

Chicago, IL, 60622

Five stars

5 (101)

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Chicago, IL, 60622

17. Emma H

Chicago, IL, 60609

Five stars

5 (82)

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Chicago, IL, 60609

18. Gabrielle J

Chicago, IL, 60607

Five stars

5 (786)

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Chicago, IL, 60607

19. Brisia S

Berwyn, IL, 60402

Five stars

5 (3)

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Berwyn, IL, 60402

20. Laura R

Riverside, IL, 60546

Five stars

5 (225)

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Riverside, IL, 60546

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.
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