Best dog walkers in Woodlawn

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

Promoted Caregiver
Kate C avatar

1. Kate C

Wag! Expert icon
Location icon

Chicago, IL, 60653

Five stars

5 (65)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60653

Promoted Caregiver
Joel  T avatar

2. Joel T

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (312)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Promoted Caregiver
Brittany A avatar

3. Brittany A

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (65)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Promoted Caregiver
Nina B avatar

4. Nina B

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

5 (430)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60605

Promoted Caregiver
Amanda H avatar

5. Amanda H

Wag! Expert icon
Location icon

Chicago, IL, 60607

Five stars

5 (95)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60607

Promoted Caregiver
Samantha J avatar

6. Samantha J

Wag! Expert icon
Location icon

Chicago, IL, 60654

Five stars

5 (400)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60654

Promoted Caregiver
Ryann K avatar

7. Ryann K

Wag! Expert icon
Location icon

Chicago, IL, 60654

Five stars

5 (153)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60654

Mark C avatar

1. Mark C

Wag! Expert icon
Location icon

Chicago, IL, 60637

Five stars

4.9 (117)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60637

Michael C avatar

2. Michael C

Wag! Expert icon
Location icon

Chicago, IL, 60615

Five stars

5 (144)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60615

Jordan M avatar

3. Jordan M

Wag! Expert icon
Location icon

Chicago, IL, 60615

Five stars

5 (118)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60615

Darnell R avatar

4. Darnell R

Wag! Expert icon
Location icon

Chicago, IL, 60619

Five stars

4.9 (172)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60619

Marchauna B avatar

5. Marchauna B

Wag! Expert icon
Location icon

Chicago, IL, 60653

Five stars

5 (185)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60653

Rachel W avatar

6. Rachel W

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

5 (276)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60616

Elizabeth D avatar

7. Elizabeth D

Wag! Expert icon
Location icon

Chicago, IL, 60609

Five stars

5 (287)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60609

Patrice W avatar

8. Patrice W

Wag! Expert icon
Location icon

Chicago, IL, 60619

Five stars

5 (74)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60619

Ashley U avatar

9. Ashley U

Wag! Expert icon
Location icon

Chicago, IL, 60617

Five stars

5 (4)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60617

Ashley D avatar

10. Ashley D

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

5 (91)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60616

John G avatar

11. John G

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (32)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Sujae V avatar

12. Sujae V

Wag! Expert icon
Location icon

Chicago, IL, 60608

Five stars

5 (51)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60608

Justin P avatar

13. Justin P

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

5 (1083)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60605

Deyannah A avatar

14. Deyannah A

Wag! Expert icon
Location icon

Chicago, IL, 60643

Five stars

4.9 (51)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60643

Emma H avatar

15. Emma H

Wag! Expert icon
Location icon

Chicago, IL, 60609

Five stars

5 (68)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60609

Joel C avatar

16. Joel C

Wag! Expert icon
Location icon

Chicago, IL, 60632

Five stars

5 (30)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60632

Grishma R avatar

17. Grishma R

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

5 (110)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60616

Valentina H avatar

18. Valentina H

Wag! Expert icon
Location icon

Chicago, IL, 60616

Five stars

5 (458)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60616

Tze N avatar

19. Tze N

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

5 (39)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60605

Taylor R avatar

20. Taylor R

Wag! Expert icon
Location icon

Chicago, IL, 60605

Five stars

5 (57)

Walk ·

Drop-In ·

Sitting ·

Boarding

Location icon

Chicago, IL, 60605

See the full listSee the full list

Wag! Walkers know Woodlawn

Woodlawn is one of Chicago's 77 community areas located on the south side of Chicago along the shores of Lake Michigan and incorporating Jackson Park. This residential neighborhood has limited commercial enterprises, however, there are many schools and churches located here including a portion of the University of Chicago along the northern border of the community. The area also includes many historic buildings and sites, including the site of the 1893 World Columbian Exposition. Visitors, as well as residents with canine companions that appreciate a daily constitutional, can explore the neighborhood on foot to take in historic landmarks. 


Because this neighborhood sits along Lake Michigan, the weather in Woodlawn is more temperate for walking than in some inland neighborhoods. Winter in Chicago is cold and summers are hot and humid. Fortunately, the lake moderates temperatures and provides cool breezes off the water on hot summer days, making walking more pleasant for those enjoying their daily outing.

What is the terrain like in Woodlawn?

Much of Woodlawn consists of residential buildings, most of which are multi-story walk-up townhouses and apartments, but some single-family residences also exist in the neighborhood. Many buildings are historic, constructed of brick, and have architectural features reflecting the time periods in which they were developed in this long-established neighborhood. The neighborhood is bounded on the north by the Midway Plaisance and the University of Chicago. 

The neighborhood is flat, and streets are comfortable to walk on foot with no inclines or steep stretches. There are many undeveloped tracts of land and some vacant properties that provide good places to walk and play with your dog. Rail tracks that run through the east side of the area form a barrier for pedestrians and their pets, so exercise caution when exploring these areas in order to avoid running afoul of any train traffic. Woodlawn is adjacent to Lake Michigan and Jackson Park is located along the shoreline of this community.

How many greenways are there in Woodlawn?

The 500-acre Jackson Park located on the east side of the community on the shores of Lake Michigan provides a flagship greenway for Woodlawn residents. This park has many trails winding through natural open areas and access to the 18-mile Chicago Lakefront Trail. Jackson Park is also connected to the Midway Plaisance with bike trails and pedestrian ways along a large, green space that stretches to Washington Park. 

Washington Park provides 366 acres of recreational and natural space. Both Washington Park and Jackson Park have lagoons and fishing and Jackson Park features a marina and beaches on the lake. These areas provide miles of walking trails and interesting natural greenways along with water for canine residents to take in on long walks near Woodlawn. There are also some smaller parks and playgrounds in the area including Anita Young Boswell Park, Flying Squirrel Pak, and numerous playlots and botanical gardens. There is no shortage of greenways in Woodlawn.

Frequently Asked Questions

How much does a dog walk cost in Woodlawn, Chicago?

plus-wag-green-icon

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

plus-wag-green-icon

How long does a dog walk last in Woodlawn, Chicago?

plus-wag-green-icon

How to book a dog walk in Woodlawn, Chicago?

plus-wag-green-icon

Is hiring a dog walker in Woodlawn, Chicago safe?

plus-wag-green-icon

How to hire a dog walker in Woodlawn, Chicago?

plus-wag-green-icon

How much do dog walkers charge in Woodlawn, 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.