South Side Pet Friendly Vacation Rentals
About South Side Vacation Rentals
There are more than 569 places to stay in South Side and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in South Side.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly South Side, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near South Side. Places to stay near South Side are 798.87 ft² on average, with prices averaging US $428 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in South Side with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 448 |
| Vacation Homes | 21 |
Use these Quick Filters to Find a Vacation Rental in South Side
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in South Side.
Weather in South Side, IL
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Stay Near South Side, IL
PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of South Side's attractions.
Other Places to Stay in South Side, IL
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:
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- McCormick Place 2BR Spacious Corner Unit with Optional Parking Sleeps 6 Guests Near Soldier Field and Grant Park
- McCormick Place Modern 2BR Loft in Downtown Chicago Michigan Avenue with Optional Parking Near Soldier Field
- Group Friendly Spacious 3BR Suite with Optional Parking and Gym Access Sleeps 10 Guest Near McCormick Place and Soldier Field
- Stylish 3BR Gem in Prime Location
- Charming 2BR Apartment with Skyline view, Optional Parking & Gym Access Near McCormick Place, Lakefront and Soldier Field
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:
- Chic Chinatown Apt w parking!
- Charming 2BR Apartment with Skyline view, Optional Parking & Gym Access Near McCormick Place, Lakefront and Soldier Field
- Comfy Chinatown Townhome and 2 garage spots!
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 569 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)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 1367 |
| The Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 622 |
| Near West Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 303 |
| South Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 271 |
| Near South Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 251 |
| Prairie District Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 192 |
| West Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 181 |
| Lower West Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 53 |
| Printers Row Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 4161 |
| Chinatown Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 3237 |
| Chicago Museum Campus Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 3309 |
