House Sitting in Old Town

See your dog's perfect match. We pair you with Old Town providers based on your dog's unique needs.

$50-100/day
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Matched to Your Dog
Curated by Pawel Kaczmarek, Founder & CEO
Updated:

House Sitting in Old Town: Rates & Availability

House Sitting in Old Town typically costs $50-$100 per day . matches you with background-checked providers based on your dog's unique needs—size, energy level, and personality.

  • Matched to Your Dog
  • Same-Day Booking
  • Background Checked
  • Old Town Locals

House Sitting in Old Town: What to Know

  • Zone 383/384 residential parking permits required - request guest pass from alderman's office
  • Street cleaning schedule varies by block - check posted signs to avoid $60 tickets
  • Wells Street nightlife noise carries to nearby units - light sleepers note
  • Victorian homes may have older plumbing/HVAC - get orientation on quirks
  • Second City shows end around 11PM - expect foot traffic surge on weekends
  • Dining and entertainment strip - Second City shows Get Directions
  • Brown Line access to Loop and North Side Get Directions

More Pet Care in Old Town

Dog Walking $25-35/walk
Dog Boarding $50-85/night
Doggy Daycare $30-55/day
Drop-In Visits $20-30/visit

House Sitting in Nearby Neighborhoods

Gold Coast Lincoln Park River North Near North Side

Frequently Asked Questions

How much does house sitting cost in Old Town?

House Sitting in Old Town typically costs $50-100/day. Prices vary based on duration, number of pets, and specific requirements. All Tails providers are background-checked and insured. See our 2026 pricing guide for more details.

What does a house sitter do in Old Town?

Tails house sitters stay overnight in your Old Town home, providing 24/7 care for your pets. This includes feeding, walks, playtime, medication, and maintaining your pet's routine. They also handle mail, plants, and basic home security.

Is house sitting better than boarding for my dog?

House sitting keeps your dog in their familiar Old Town environment, reducing stress—especially beneficial for anxious dogs, seniors, or those on strict schedules. Boarding offers more socialization. The best choice depends on your dog's personality.

How do I book house sitting in Old Town?

Download the Tails app, enter your Old Town address, and browse verified providers. View profiles, read reviews, and book directly. All providers are background-checked, insured, and trained. You can message providers before booking and receive photo updates during service.

Old Town Local Conditions

Traffic Level

medium

Walkability

excellent — wide sidewalks, short blocks

Street Cleaning

Varies by block - check posted signs. Residential typically Wednesdays or Thursdays 9AM-1PM (Apr-Nov)

Winter Parking

Affected by 2"+ snow ban (3AM-7AM)

4.9

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