South Side Pet Friendly Vacation Rentals
About South Side Vacation Rentals
There are more than 588 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 851.64 ft² on average, with prices averaging US $494 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 | 474 |
| 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:
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
- Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- 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
- Large 4BR Cozy Stay Near Field Museum & McCormick
- South Loop · 3 Kings · Steps from McCormick Place
- Group-Friendly 6BR Luxury Suite in Prime South Loop Location with Optional Parking and Gym Access Near McCormick Place, Soldier Field and Grant Park
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:
- 2-bedroom condo in perfect Chicago with WiFi, AC. Start your getaway
- McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field
- Chic Chinatown Apt w parking!
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 588 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 | 1316 |
| The Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 593 |
| South Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 341 |
| Near South Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 326 |
| Prairie District Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 270 |
| Near West Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 268 |
| West Loop Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 159 |
| Lower West Side Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 54 |
| Printers Row Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 4130 |
| Chinatown Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 3211 |
| Chicago Museum Campus Pet Friendly Hotels and Vacation Rentals in Chicago, Illinois | 3309 |
