South Side Pet Friendly Vacation Rentals

Frequently Asked Questions About South Side?

What are the top vacation rentals in South Side?

Find the best options in or near South Side for pet-friendly travel. If you are planning a trip or vacation in South Side, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in South Side:

• MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
• Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
• Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
• Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
• Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
• Luxéry Stay "Game of Thrones" Downtown/McCormick/WinTrust Area
• Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
• Luxury 6BR Loft Suite Perfect for 12 Guests with Skyline Views, Optional Parking and Gym Access Near McCormick Place and Soldier Field
• Group-Friendly 6BR Luxury Suite in Prime South Loop Location with Optional Parking and Gym Access Near McCormick Place, Soldier Field and Grant Park
• Group Friendly Spacious 3BR Suite with Optional Parking and Gym Access Sleeps 10 Guest Near McCormick Place and Soldier Field

How many vacation rentals have private pools in South Side?

We have found 1 accommodation options with private pools in or near South Side, many of which accept and welcome pets. Top-rated hotels, resorts,and places to stay that have access to a swimming pool include:

• Blueground South Loop pool golf sim nr museum CHI-1047

Which vacation homes in South Side are best for families?

Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in South Side? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in South Side:

• Modern South Loop 1BR w/Gym & Pool, nr Grant Park, by Blueground
• McCormick Place 2BR Suite with Patio, Skyline View and Optional Parking Sleeps 6 Near Soldier Field and Grant Park
• Modern South Loop 1BR w/Pool + Gym, walk to Soldier Field, by Blueground

How many PetFriendly vacation rentals are available in South Side?

PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 528 in the South Side area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in South Side.

Nearby Neighborhood (11)