Compare HOTELS, RESORTS, AND RENTALS in South Side, Illinois, USA
About South Side Vacation Rentals
There are more than 569 places to stay in South Side that are available. These options include 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 places to stay in South Side.
Are you seeking a last-minute 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 Hotala South Side, you can quickly compare different options to find the hottest deals with a single click. Looking for 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 $431 a night.
Hotala 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 reservation today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods South Side, IL
Frequently Asked Questions About South Side?
What are the top hotels or resorts in South Side?
You have a lot of choices in or near South Side. If you need a hotel in the South Side area, consider making a reservation for a few nights at one of our suggested properties as these have been known to be the Top Vacation Rentals and Places to Stay in South Side:
- Charming 2BR Unit Near McCormick Place & Millennium Park
- Spacious 2BR in Chicago Near McCormick Sleeps 8
- Skyline 2BR 2BA in South Loop Near Museums & McCormick Place
- SpringHill Suites by Marriott Chicago Chinatown
- Stylish 2BR Cozy South Loop Suite Near McCormick
- McCormick South Loop 2BR Suite Near Soldier Field & Museum Campus
- Hyatt Regency McCormick Place Chicago
- Marriott Marquis Chicago
- Home2 Suites by Hilton Chicago McCormick Place
- The Wheeler Mansion
How many hotels, resorts, or rentals are available in South Side?
At present, the total number of properties listed by Hotala -- including hotels, resorts, and rentals -- as of 2026 is over 569 in the South Side area, and still growing. By combining listings from multiple websites, Hotala provides a huge selection of the best hotels, resorts, and vacation properties in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Hotel & Resort Deals in Chicago, Illinois | 1383 |
| The Loop Hotel & Resort Deals in Chicago, Illinois | 633 |
| Near West Side Hotel & Resort Deals in Chicago, Illinois | 303 |
| South Loop Hotel & Resort Deals in Chicago, Illinois | 273 |
| Near South Side Hotel & Resort Deals in Chicago, Illinois | 253 |
| Prairie District Hotel & Resort Deals in Chicago, Illinois | 193 |
| West Loop Hotel & Resort Deals in Chicago, Illinois | 181 |
| Lower West Side Hotel & Resort Deals in Chicago, Illinois | 54 |
| Printers Row Hotel & Resort Deals in Chicago, Illinois | 4161 |
| Chinatown Hotel & Resort Deals in Chicago, Illinois | 3237 |
| Chicago Museum Campus Hotel & Resort Deals in Chicago, Illinois | 3309 |
