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South Side Hotels, Resorts, and Rentals

About South Side Vacation Rentals

There are more than 512 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 922.64 ft² on average, with prices averaging US $425 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.

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Top Hotels, Resorts, Rentals, Villas, Vacation Homes, Cottages, B&B and Cabins Accommodation Types in South Side

Type Count
Holiday Apartments 421
Vacation Homes 14

Use these Quick Filters to Find a Vacation Rental in South Side

★ Pro Tip: Hotala 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.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Stay Near South Side's Top Attractions

Hotala can help you find hotels, resorts, and rentals near many of South Side's top attractions, neighborhoods, and points of interest.


McCormick Place
Soldier Field
John G. Shedd Aquarium
Field Museum of Natural History
Wintrust Arena
Willie Dixon's Blues Heaven
Glessner House Museum
Film Row Cinema
Olmec Head No 8
Clarke House Museum
Prairie Avenue Historic District
Chicago Women's Park
National Vietnam Veterans Art Museum
Elbridge G Keith House
Ping Tom Memorial Park
Joseph G Coleman House
William K Kimball House
Gen. John Logan Memorial
On Leong Building
Grant Park

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Film Row Cinema 3,945 Properties
Dearborn Park 3,938 Properties
Gen. John Logan Memorial 3,932 Properties
Field Museum of Natural History 3,763 Properties
John G. Shedd Aquarium 3,734 Properties
Olmec Head No 8 3,727 Properties
Ping Tom Memorial Park 3,684 Properties
National Vietnam Veterans Art Museum 3,553 Properties
Chinatown 3,053 Properties
South Loop 375 Properties
Near South Side 363 Properties
Prairie District 260 Properties

Complexes around South Side, IL


Wells Apartments St Chicago 31 Properties
South Loop Grant Park 29 Properties
Town 16 Properties
Sonder South Wabash 11 Properties
Mccormick Place 5 Properties
Grant Park Hotel 3 Properties
Michigan Avenue 3 Properties

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:

How many vacation rentals have private pools in South Side?

There are 2 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:

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 2025 is over 512 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 1796
The Loop Hotel & Resort Deals in Chicago, Illinois 777
South Loop Hotel & Resort Deals in Chicago, Illinois 375
Near South Side Hotel & Resort Deals in Chicago, Illinois 363
Near West Side Hotel & Resort Deals in Chicago, Illinois 331
Prairie District Hotel & Resort Deals in Chicago, Illinois 260
West Loop Hotel & Resort Deals in Chicago, Illinois 200
Lower West Side Hotel & Resort Deals in Chicago, Illinois 44
Chinatown Hotel & Resort Deals in Chicago, Illinois 3053
Printers Row Hotel & Resort Deals in Chicago, Illinois 4021
Chicago Museum Campus Hotel & Resort Deals in Chicago, Illinois 3407

People Also Ask

There are 45 hotels in South Side and 435 rentals

Recently Booked Hotels, Resorts, or Rentals in South Side