South Side Accommodations - Hotels & Rentals
About South Side Vacation Rentals
Discover More than 571 Incredible Getaway Rentals Available in South Side. Choose from a Wide Selection of Villas, Hotels, and Other Rental Options. Explore Luxury Amenities at Affordable Prices, Creating the Ideal Base for Your Next Vacation. Plan Your Perfect Escape with Online Reservations and Uncover Fantastic Stays in South Side.
Online Reservations Offers Numerous Last-Minute Deals on Villas, Hotels, and Rentals, Both Near You and Across the Globe. Whether You Need Accommodation for a Group or an Event, Be it a Hotel or Vacation Rental (Including Cabins and Private Luxury Villas), We're Here to Assist. With Online Reservations in South Side, You Can Easily Compare Options from Multiple Suppliers with a Single Click to Find the Perfect Price Point, Amenities, and Style of Stay That Suit Your Needs. Looking for Group Deals, Properties with Private Pools, Hot Tubs, Pet-Friendly Options, or Spacious Master Suite Bedrooms with Open-Air Showers? You Can Find It All in the Online Reservations Vacation Rentals, Resorts, and Airbnb-Style Properties in South Side. The Average Size of Places to Stay Near South Side is 854.64 ft², with Prices Averaging US $505 per Night.
Let Online Reservations Help You Discover the Ideal Holiday Rental to Create Lifelong Travel Memories in South Side. Our Listed Prices Are Often Discounted Compared to Rack Rates. Simply Search for Your Destination and Secure the Perfect Place to Stay Today.
Top Hotels & Vacation Rentals in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 472 |
| Vacation Homes | 20 |
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★ Pro Tip: Online Reservations is a vacation rental website specializing in cottages, lake houses, and exclusive summer home rentals. We curate a vast selection of incredible properties from trusted suppliers, allowing you to compare prices and locations to find the perfect fit for your getaway. Create lasting memories in South Side with Online Reservations.
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.
Activities South SideGuest Reviews Local Attractions
A Large Selection of Hotels and Vacation Rentals from Around the World South SideGuest Reviews Discover Exciting Activities and Must-Visit Destinations for Your Upcoming Journey
Find Hotels & Vacation Rentals in these Cities and Neighborhoods
Frequently Asked Questions About South Side?
What are the top hotels, lake houses & vacation rentals in South Side?
We provide an array of great vacation destinations in South Side. If you are looking to stay in or around the South Side area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in South Side:
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
- McCormick 3B/2Ba w optional parking/Up to 8 guests
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
- Luxéry Stay South Loop - McCormick/Wintrust Area
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
How many Hotels & Vacation Rentals have private pools in South Side?
We have 2 Hotels & Vacation Rentals featuring a private pool in and near South Side. Some of the best destinations to stay that feature or have access to a swimming pool are:
Which hotel, lake house, or vacation rental in South Side is best for families?
Searching for a family-friendly getaway in South Side? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- Modern and Bright 2BR on Michigan Ave with Optional Parking and Gym Access Near Soldier Field & Grant Park
- The Wheeler Mansion
- Convenient 2BR Suite in Prime Location with Gym Access & Optional Parking Near McCormick Place and Soldier Field
How many hotels, resorts, or rentals are available in South Side?
Online Reservations™ offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Online Reservations™ in 2026 is over 571 in the South Side area, and that number rises every day. By combining listings from multiple websites and travel providers, Online Reservations™ can provide you with a diverse amount of choices of the best luxury stays in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1501 |
| The Loop Vacation Rentals in Chicago, Illinois | 672 |
| South Loop Vacation Rentals in Chicago, Illinois | 384 |
| Near South Side Vacation Rentals in Chicago, Illinois | 369 |
| Near West Side Vacation Rentals in Chicago, Illinois | 323 |
| Prairie District Vacation Rentals in Chicago, Illinois | 272 |
| West Loop Vacation Rentals in Chicago, Illinois | 184 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 57 |
| Printers Row Vacation Rentals in Chicago, Illinois | 3937 |
| Chinatown Vacation Rentals in Chicago, Illinois | 2998 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3119 |
