Top Rated Activities & Tours in South Side
South Side Vacation Rentals, Hotels, & Places to Stay
About South Side Vacation Rentals
There are more than 588 places to stay that are available in South Side. These choices include hotels as well as other short-term private accommodations (including vacation rentals, cabins, condos, RVs, and more), have a wide selection of amenities at great prices, providing you with all the comforts of home or a touch of luxury. We like to help you find more room with Varoom when booking your property in South Side.
Varoom features many last-minute deals on hotels, resorts and places to stay including many that are nearby. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Varoom's places in South Side, you have the flexibility of comparing different options from multiple suppliers with a single click. Group deals, private pools, hot tubs, allows pets, or even those with huge master suite bedrooms with open-air showers? You can find vacation rentals and resorts as well as Airbnb-style properties in South Side. Places to stay near South Side are 851.64 ft² on average, with prices averaging US $494 a night.
Varoom helps you discover places to stay and suggests things to do to create great travel memories in South Side. Prices listed are often found to be at a 30-40% discount versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Top Rental Accommodation Types 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: Varoom is a meta travel and activities site, and as such we combine results from many of the leading travel websites, helping you compare the best places to stay and things to do in each market. Use the filter option to narrow down your selection and let us help you find more room to stay, play, and discover. Create new memories in South Side today.
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.
Top Attractions Around South Side, IL
Varoom offers a large selection of top attractions around South Side . Research things to do on your vacation before you visit South Side.
Other Places to Stay in South Side, IL
Complexes around South Side, IL
Frequently Asked Questions About South Side?
What are the top vacation rentals in South Side?
We have scoured the web to find you options in South Side. If you plan on staying near or in the South Side area, consider one of the following places to stay for a week or more. Weekly stays are a great way to unwind and unplug. These places to stay have all been rated as one of the Top Places to Stay in South Side:
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- Cozy Downtown MICH AVE #7 | gym+rooftop
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- McCormick 6B/4Ba Luxury Suite for groups/12 guests
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- 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
How many vacation rentals have private pools in South Side?
We have found 2 places to stay that feature a private swimming pool in or near South Side. Some of the best places to stay that feature or have access to a swimming pool are:
Which vacation homes in South Side are best for families?
If you are looking for a place to stay that is family-friendly in South Side, check out one of the following places as all are highly-rated options and have received excellent reviews for families or groups staying in South Side:
- McCormick Place 2b/2b corner unit with optional parking for up to 6 guests
- McCormick Place 2BR Oasis with Optional Parking, Patio, Gym for up to 6 guests Near Museum Campus, Grant Park & Soldier Field
- Marriott Marquis Chicago
How many Varoom vacation rentals are available in South Side?
Varoom updates its properties nightly to bring you a great selection of places to stay. Currently, the total number of properties listed by Varoom 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, Varoom can provide you with a diverse amount of choice of the best places to stay in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 1316 |
| The Loop Vacation Rentals in Chicago, Illinois | 593 |
| South Loop Vacation Rentals in Chicago, Illinois | 341 |
| Near South Side Vacation Rentals in Chicago, Illinois | 326 |
| Prairie District Vacation Rentals in Chicago, Illinois | 270 |
| Near West Side Vacation Rentals in Chicago, Illinois | 268 |
| West Loop Vacation Rentals in Chicago, Illinois | 159 |
| Lower West Side Vacation Rentals in Chicago, Illinois | 54 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4130 |
| Chinatown Vacation Rentals in Chicago, Illinois | 3211 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3309 |
