South Side Hotels, Resorts, and Rentals
About South Side Vacation Rentals
There are more than 529 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 891.63 ft² on average, with prices averaging AU $554 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.
Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 431 |
| Vacation Homes | 20 |
Use these Quick Filters to Find a Vacation Rental in South Side
★ Pro Tip: Hotala.com.au has aggregated the supply of many of the leading websites including providers of short-term rentals, OTAs (including Booking.com, Agoda, Airbnb, and others). Use the Advanced Filter feature at the top to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and more. We want to help you find the hottest places and best places to stay in South Side.
Weather in South Side, IL
View the weather forecast for South Side before booking your South Side Vacation Rentals to confirm your best time to go.
Stay Near South Side's Top Attractions
Hotala.com.au can help you find hotels, resorts, and rentals near many of South Side's top attractions, neighborhoods, and points of interest.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
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:
- McCormick South Loop 2BR Suite Near Soldier Field & Museum Campus
- Stylish 2BR Cozy South Loop Suite Near McCormick
- SpringHill Suites by Marriott Chicago Chinatown
- Hyatt Regency McCormick Place Chicago
- Marriott Marquis Chicago
- Home2 Suites by Hilton Chicago McCormick Place
- Hampton Inn Chicago McCormick Place
- SpringHill Suites by Marriott Chicago Chinatown
- Home2 Suites By Hilton Chicago McCormick Place
- The Wheeler Mansion
How many vacation rentals have private pools in South Side?
There are 1 accommodation options with private pools in or near South Side. Top-rated hotels, resorts, and places to stay that have access to a swimming pool include:
Which hotel or resort in South Side is best for families?
If you are looking for a family-friendly hotel, resort, or vacation home in South Side, check out one of the following places to stay as all are highly-rated accommodation choices with excellent reviews for families or groups staying in South Side:
- Budget-Friendly Room| Free Coffee | Downtown
- Spacious 3BR in South Loop Near McCormick - Optional Parking
- Bright 3BR Retreat Near McCormick + Museum Campus
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 529 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 | 1548 |
| The Loop Hotel & Resort Deals in Chicago, Illinois | 717 |
| Near West Side Hotel & Resort Deals in Chicago, Illinois | 371 |
| South Loop Hotel & Resort Deals in Chicago, Illinois | 366 |
| Near South Side Hotel & Resort Deals in Chicago, Illinois | 351 |
| Prairie District Hotel & Resort Deals in Chicago, Illinois | 251 |
| West Loop Hotel & Resort Deals in Chicago, Illinois | 214 |
| Lower West Side Hotel & Resort Deals in Chicago, Illinois | 55 |
| Printers Row Hotel & Resort Deals in Chicago, Illinois | 3802 |
| Chinatown Hotel & Resort Deals in Chicago, Illinois | 2948 |
| Chicago Museum Campus Hotel & Resort Deals in Chicago, Illinois | 3119 |
