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Best dog walkers in Oakland

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

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Top dog walkers in Oakland

Promoted Caregiver
Stacy B avatar

1. Stacy B

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Chicago, IL, 60621

Five stars

4.9 (3625)

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Chicago, IL, 60621

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Monica B avatar

2. Monica B

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Chicago, IL, 60605

Five stars

4.9 (82)

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Chicago, IL, 60605

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Joseph  H avatar

3. Joseph H

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Chicago, IL, 60611

Five stars

5 (35)

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Chicago, IL, 60611

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Kaitlyn H avatar

4. Kaitlyn H

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Chicago, IL, 60607

Five stars

4.9 (62)

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Chicago, IL, 60607

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Jaime H avatar

5. Jaime H

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Chicago, IL, 60654

Five stars

5 (39)

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Chicago, IL, 60654

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Ernesto O avatar

6. Ernesto O

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Chicago, IL, 60608

Five stars

4.8 (231)

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Chicago, IL, 60608

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Julyssa R avatar

7. Julyssa R

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Chicago, IL, 60612

Five stars

4.9 (101)

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Chicago, IL, 60612

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Bohdan M avatar

8. Bohdan M

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Chicago, IL, 60614

Five stars

5 (1)

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Chicago, IL, 60614

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Kaitlyn G avatar

9. Kaitlyn G

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Chicago, IL, 60622

Five stars

4.9 (158)

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Chicago, IL, 60622

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Katherine P avatar

10. Katherine P

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Chicago, IL, 60622

Five stars

4.8 (24)

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Chicago, IL, 60622

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Natalie A avatar

11. Natalie A

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Chicago, IL, 60657

Five stars

5 (36)

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Chicago, IL, 60657

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Jose R avatar

12. Jose R

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Chicago, IL, 60651

Five stars

4.9 (52)

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Chicago, IL, 60651

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Will P avatar

13. Will P

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Chicago, IL, 60613

Five stars

4.9 (1900)

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Chicago, IL, 60613

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Edwin T avatar

14. Edwin T

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Chicago, IL, 60639

Five stars

4.8 (442)

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Chicago, IL, 60639

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Natalie M avatar

15. Natalie M

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Chicago, IL, 60639

Five stars

4.9 (43)

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Chicago, IL, 60639

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Marchauna B avatar

1. Marchauna B

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Chicago, IL, 60653

Five stars

4.9 (173)

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Chicago, IL, 60653

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Bianca C avatar

2. Bianca C

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Chicago, IL, 60616

Five stars

4.9 (873)

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Chicago, IL, 60616

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Flora F avatar

3. Flora F

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Chicago, IL, 60616

Five stars

5 (17)

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Chicago, IL, 60616

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Sydney V avatar

4. Sydney V

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Chicago, IL, 60615

Five stars

5 (11)

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Chicago, IL, 60615

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Dan C avatar

5. Dan C

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Chicago, IL, 60615

Five stars

5 (18)

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Chicago, IL, 60615

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Maggie L avatar

6. Maggie L

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Chicago, IL, 60615

Five stars

4.7 (31)

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Chicago, IL, 60615

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Maria D avatar

7. Maria D

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

4.1 (21)

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Chicago, IL, 60616

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Nicole K avatar

8. Nicole K

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Location icon

Chicago, IL, 60609

Five stars

4.9 (72)

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Chicago, IL, 60609

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Justin P avatar

9. Justin P

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Chicago, IL, 60605

Five stars

4.9 (263)

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Chicago, IL, 60605

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Janet V avatar

10. Janet V

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Chicago, IL, 60609

Five stars

4.9 (3254)

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Chicago, IL, 60609

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Felicia L avatar

11. Felicia L

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

5 (19)

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Drop-In

Sitting

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Chicago, IL, 60616

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Jayla H avatar

12. Jayla H

Wag! Expert icon
Location icon

Chicago, IL, 60609

Five stars

5 (2)

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Chicago, IL, 60609

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Sujae V avatar

13. Sujae V

Wag! Expert icon
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Chicago, IL, 60608

Five stars

5 (40)

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Drop-In

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Boarding

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Chicago, IL, 60608

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Athena T avatar

14. Athena T

Wag! Expert icon
Location icon

Chicago, IL, 60621

Five stars

4.9 (329)

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Boarding

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Chicago, IL, 60621

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Ashleigh H avatar

15. Ashleigh H

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Chicago, IL, 60605

Five stars

5 (39)

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Chicago, IL, 60605

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Evelyn B avatar

16. Evelyn B

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Location icon

Chicago, IL, 60637

Five stars

4.4 (11)

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Chicago, IL, 60637

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Gabrielle J avatar

17. Gabrielle J

Wag! Expert icon
Location icon

Chicago, IL, 60607

Five stars

4.9 (232)

Walk

Drop-In

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Boarding

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Chicago, IL, 60607

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Lindsey L avatar

18. Lindsey L

Wag! Expert icon
Location icon

Chicago, IL, 60611

Five stars

5 (35)

Walk

Drop-In

Sitting

Boarding

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Chicago, IL, 60611

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Tze N avatar

19. Tze N

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

4.9 (31)

Walk

Drop-In

Sitting

Boarding

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Chicago, IL, 60605

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Alexandra  W avatar

20. Alexandra W

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

4.9 (100)

Walk

Drop-In

Sitting

Boarding

Location icon

Chicago, IL, 60605

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Wag! Walkers know Oakland

Nestled up against the seven-mile strip of Lincoln Park, Oakland is one of the 77 officially recognized communities that make up Greater Chicago. Not too long ago, Oakland's skyline was defined by many housing projects. However, many of them have been torn down and are being replaced by condos and new single-family homes as this old part of the Greater Chicago area is slowly enjoying a rebirth. The district does still have a large percentage of multifamily housing, but there are plenty of sidewalks for you and your four-legged friend to make good use of. Sitting on the shore of Lake Michigan can make winters here frigid with high winds and low wind-chill factors to deal with along with a significant amount of snow. Spring, summer, and fall typically range from warm to hot and humid. During the summer months, you may want to get your walks in early in the morning or later in the evening.聽

What is the terrain like in Oakland?

The terrain here is much the same as most of Greater Chicago in that it is incredibly flat. It is so flat you can stand at one end of S. Lake Park Ave. and see all the way to the other end. Although you might think flat terrain makes for a boring walk, it does give the two of you a way to rack up the miles. Many of the sidewalks are crumbling and you really need to pay attention while you are walking. In the southern section of Oakland, many of the streets are tree lined and have grass strips for your pup to pee on. In the northern section, trees seem to have taken a back seat or been lost to the elements as they become few and far between along most of the sidewalks, leaving you exposed to the summer sun if you go walking during the day.聽

How many greenways are there in Oakland?

Oakland has a pretty large selection of green spaces in comparison to many of the surrounding communities. There are several parks in the community to take your pup for a walk in, but there are far more vacant lots that have grown over where you may also be able to take your pooch out on to do his business. Keep in mind that just because it might be an abandoned lot, you still need to clean up after he goes.聽

On the east side of Oakland lies Burnham Park: a six-mile stretch of trails, grass, and trees that you and your dog can spend countless hours in. The park also gives you access to the 41st Street Beach where the two of you can cool off on a hot summer day. If the beach doesn't sound right, there are several parks scattered through Oakland that are pet-friendly and great places to take your pooch out for a little exercise.

Frequently Asked Questions

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