Old Town Triangle pet-friendly rentals

We found 52 pet-friendly rentals — enter your dates for availability

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September 2025

October 2025

Explore Old Town Triangle pet-friendly rentals

Premier Host

Walk to the Beach! Theater-Coffee Bar-Games-Gym

Sleeps 12 · 4 bedrooms · 1 bathroom

When you arrive, the main floor is open - living room, dining table, and kitchen all share a bright room with cathedral ceilings

Old Town Chicago at it's finest! Pet Friendly & Recently Renovated Top-Floor Condo Has Everything You Need for a Perfect Windy City Getaway by AllSet Turnover

Sleeps 4 · 2 bedrooms · 2 bathrooms

Top rated pet-friendly rentals - Old Town Triangle

Premier Host

Excellent property for a large group.

We had a group of 30 stay across the two houses. They were very clean, adequately equipped and incredibly spacious for our group. Would definitely recommend Inna's property for any group large or small.

Mark W.

Stayed July 2022

Enjoyed

Property was everything as described.Perfect location. Sonia really looks after her guests, even with some fresh supplies in the fridge, and fresh bread and eggs etc. Would recommend this location, also close to the L train!

Brent N.

Stayed May 2024

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