Discover Your Perfect South Side Vacation Homes

Best Vacation Homes in South Side

See More South Side Vacation Rentals

South Side Luxury Rentals

See More South Side Luxury Vacation Rentals
Find More South Side Villas, Resorts, & Rentals on BedroomVillas

South Side Pet Friendly Vacation Rentals

See More Pet-Friendly Vacation Rentals in South Side on PetFriendly.io

South Side Large Vacation Homes

7.2 (7 Reviews)
Apartment
South Loop 2 Bedroom Apt
  • Air Conditioner
  • TV
  • Security/Safety
View Availability
See More Family Vacation Rentals in South Side on FVR

Why Choose Rent By Owner for your South Side Vacation Rental Homes?

What makes our Vacation Rentals special?

image
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
image
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
image
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for South Side Vacation Rentals

Where are the best neighborhoods to stay in South Side?

Exploring the neighborhoods in South Side, Illinois offers a unique opportunity to experience a vibrant and diverse community. Whether you're seeking a lively atmosphere or a quieter retreat, South Side's areas provide a range of options for your stay. When booking your vacation rentals within this region, you'll find accommodations that cater to different preferences and budgets, helping you make the most of your visit. Discover the authentic charm of South Side by choosing a neighborhood that aligns with your travel itinerary, ensuring a comfortable and memorable experience throughout your stay.

Downtown Chicago

Staying in this central area offers unparalleled access to vibrant city life and iconic sights, making it an ideal choice for exploring the region’s bustling urban scene. The neighborhood's strategic location provides a comfortable base for discovering everything here has to offer.

View 1791+ Rentals in Downtown Chicago

The Loop

This downtown district is perfect for those seeking proximity to cultural attractions and business hubs, with convenient transportation options that simplify your exploration of the broader region. Choosing here means you'll be at the heart of Chicago's dynamic atmosphere.

View 775+ Rentals in The Loop

South Loop

Offering a blend of residential charm and access to major attractions, this area is ideal for travelers who want both comfort and convenience during their stay. It’s a popular choice for experiencing the local vibe while remaining close to the city’s highlights.

View 372+ Rentals in South Loop

West Loop

Known for its trendy dining scene and creative energy, this neighborhood attracts visitors looking to enjoy the region’s vibrant culinary culture. Staying here places you near some of the best local eateries and entertainment options.

View 198+ Rentals in West Loop

Near South Side

This diverse neighborhood offers easy access to cultural institutions and green spaces, making it suitable for travelers interested in both leisure and exploration. Its strategic location makes it simple to navigate around the region.

View 360+ Rentals in Near South Side

Chinatown

Experience the rich cultural heritage of the area by staying in this vibrant neighborhood, which provides unique dining, shopping, and cultural experiences within close reach. It’s a great base for immersing yourself in the local community.

View 3053+ Rentals in Chinatown

Near West Side

This lively district combines historical significance with modern development, offering a range of attractions and amenities that appeal to many travelers. It serves as a convenient starting point for exploring the city's diverse neighborhoods.

View 331+ Rentals in Near West Side

Printers Row

Ideal for book lovers and history enthusiasts, this charming area features historic architecture and literary history, providing a peaceful yet centrally located setting for your stay in the region.

View 4021+ Rentals in Printers Row

Best Times to Visit South Side

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience, allowing you to enjoy the area’s local events and favorable weather conditions when planning your stay in South Side, Illinois.

Peak Season Highlights

summer
Summer (June to August)

During the peak summer months, you can enjoy warm weather and longer days in this destination, making it ideal for outdoor activities and exploring the area's vibrant local scene.

Average Temperature Daytime: 85°F - Nighttime: 65°F
autumn
Fall (September to November)

Early fall offers comfortable temperatures and beautiful natural scenery, attracting visitors to experience the region's seasonal changes and outdoor attractions.

Average Temperature Daytime: 75°F - Nighttime: 55°F

Off-Season Highlights

image
Winter (December to February)

In winter, the area experiences cooler temperatures which can be perfect for those seeking quieter times and lower rates when booking vacation rentals.

Average Temperature Daytime: 40°F - Nighttime: 25°F
image
Spring (March to May)

Late winter to early spring sees milder weather and fewer crowds, offering a peaceful escape while enjoying the emerging natural beauty of the region.

Average Temperature Daytime: 60°F - Nighttime: 40°F

Weekly Weather Forecast for South Side

How to Book Your South Side Vacation Rental Home

What's our booking process?

Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Explore and book the perfect rental in South Side

More Top-Rated Vacation Rentals in South Side Area

Common Vacation Rentals Amenities

What amenities can you expect?

Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Outdoor Amenities

  • Enjoy a private outdoor patio or balcony to relax and take in the surroundings.
  • Benefit from accessible outdoor grilling areas for delicious meals al fresco.
  • Take advantage of shared or private swimming pools perfect for cooling off during your stay.
  • Explore landscaped gardens or lush lawns that provide tranquil lounging spots.
  • Make use of dedicated outdoor dining spaces for memorable meals outdoors.
  • Utilize on-site parking facilities to conveniently come and go during your visit.
  • Experience outdoor recreational amenities such as tennis courts or sports fields, ideal for active guests.

Top Attractions Around South Side

What attractions are nearby?

While here, you can explore a variety of engaging activities nearby, from local parks and cultural sites to vibrant dining options, all conveniently accessible within the region surrounding your vacation rental in South Side, Illinois.

image
image

Family Activities

  • Adler Planetarium: Explore the stars and enjoy interactive exhibits that captivate the whole family at this leading science institution in the region.
  • Shedd Aquarium: Discover marine life through engaging displays and immersive experiences, making it a must-visit attraction here for families seeking educational fun.
  • Field Museum of Natural History: Journey through natural history with fascinating exhibits that inspire curiosity and learning for children and adults alike.
  • Millennium Park: Relax and enjoy outdoor activities, art installations, and family-friendly events in this iconic park close to the area’s vibrant cityscape.
image

Adult Activities

  • Visit the South Side Community Art Center: Engage with vibrant local art and culture at this historic hub, perfect for art enthusiasts seeking a cultural experience in the area.
  • Explore Lake Michigan’s South Shore: Enjoy outdoor activities along the shoreline, where scenic views and tranquil beaches offer a relaxing escape close to your vacation rental.
  • Discover the Museum of Science and Industry – Chicago: A short drive from here, this renowned museum provides hands-on exhibits that appeal to those interested in science and innovation.
  • Attend live performances at the South Side music venues: Experience the region’s lively music scene by catching concerts and shows that celebrate local talent and diversity.

Other Places to Stay in South Side, IL

Film Row Cinema
Film Row Cinema Vacation Rentals
Dearborn Park
Dearborn Park Vacation Rentals
Gen. John Logan Memorial
Gen. John Logan Memorial Vacation Rentals
Field Museum of Natural History
Field Museum of Natural History Vacation Rentals
John G. Shedd Aquarium
John G. Shedd Aquarium Vacation Rentals
Olmec Head No 8
Olmec Head No 8 Vacation Rentals
Ping Tom Memorial Park
Ping Tom Memorial Park Vacation Rentals
National Vietnam Veterans Art Museum
National Vietnam Veterans Art Museum Vacation Rentals
Chinatown
Chinatown Vacation Rentals
South Loop
South Loop Vacation Rentals
Near South Side
Near South Side Vacation Rentals
Prairie District
Prairie District Vacation Rentals
More Places to Stay Near South Side

South Side Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead: Research local events and seasonal attractions to maximize your experience here and ensure your vacation rental aligns with your interests.
  • Explore Neighborhoods: Take time to discover various districts within the area, as each offers unique charm and authentic local experiences nearby your stay.
  • Utilize Local Transportation: Familiarize yourself with public transit options and walking routes to navigate conveniently and enjoy the region’s scenery without hassle.
  • Connect with Locals: Engage with community members or hosts to gain insider tips that can enrich your visit and help you uncover hidden gems around your accommodation.

Transportation Options

  • Chicago Transit Authority (CTA) Metro Trains: The CTA provides convenient rail and bus services connecting this part of Illinois with the broader Chicago area, making it easy for you to explore locally or commute to nearby attractions.
  • Local Bus Services: Several bus routes operate throughout the region, offering flexible and affordable transportation options for your day-to-day travel needs while staying in South Side's vacation rentals.
  • Taxi and Rideshare Services: Taxis and rideshare companies like Uber and Lyft are readily available here, providing quick and reliable transportation directly from your rental property to key destinations.
  • Regional Airport Access: The area is served by major airports with accessible shuttle and car rental services, ensuring seamless connections for your arrival and departure plans within Illinois.

Local Customs Options

  • Respect for Local History: Engaging with the area's rich historical background is a common custom, reflecting appreciation for its cultural heritage.
  • Community Gatherings: Participating in neighborhood festivals and events showcases the region's warm sense of community and local pride.
  • Cuisine Appreciation: Embracing local culinary traditions, from traditional dishes to regional specialties, is a notable part of visiting here.
  • Environmental Respect: Practicing eco-friendly habits and conservation efforts aligns with the area's commitment to preserving its natural surroundings.

Frequently Asked Questions About South Side?

1. What are the top vacation rentals in South Side?

There are a lot of options in South Side. If you plan on staying in the South Side area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in South Side:

2. How many vacation rentals have private pools in South Side?

There are 5 vacation rentals with private pools near South Side. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in South Side are best for families?

If you are looking for a family-friendly vacation home in South Side, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in South Side:

4. How many Rentbyowner vacation rentals are available in South Side?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 504 in the South Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in South Side. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the individual property listing. To understand the specific terms, review the cancellation details provided in the listing or contact the property owner directly.

6. Are there any additional fees I should be aware of when booking a rental here?

Additional fees such as cleaning, service charges, or taxes are typically outlined in the listing details. It's recommended to read through the full description or reach out to the host for clarification.

7. How do I verify the safety and cleanliness standards of a vacation rental in this region?

Properties are often reviewed and rated by previous guests, and detailed descriptions usually include information about safety and cleanliness measures. For specific concerns, contacting the local host ensures you receive accurate details.

8. What amenities are commonly available with rentals in this part of Illinois?

Most vacation rentals in the area offer essential amenities such as Wi-Fi, kitchen facilities, and parking. To confirm specific features, consult the property listing or communicate with the owner beforehand.

9. What should I know about checking in and out at vacation properties here?

Check-in and check-out procedures are detailed in each listing. It’s advisable to follow the instructions provided by the host or contact them directly for any special arrangements or questions.

South Side Top Rated Vacation Rentals

See More South Side Vacation Rentals