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Old Town Chicago pet-friendly rentals

We found 435 pet-friendly rentals — enter your dates for availability

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August 2025

September 2025

Explore Old Town Chicago pet-friendly rentals

Level Chicago – Old Town

Sleeps 8

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Sleeps 22 · 5 bedrooms · 3+ bathrooms

Top rated pet-friendly rentals - Old Town Chicago

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

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