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  4. Near South Side
  5. Rentals by Owner

Discover Your Perfect Near South Side Rentals by Owner

Near South Side Rentals by Owner

More Top-Rated Rentals by Owner in Near South Side Area

Why Choose Rent By Owner for your Near South Side vacation rental?

What makes our Rentals by Owner special?

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

Popular Areas for Near South Side Rentals by Owner

Where are the best neighborhoods to stay in Near South Side?

When choosing where to stay in Chicago, the Near South Side offers a vibrant and conveniently located neighborhood that caters to travelers seeking both comfort and accessibility. This area provides a variety of rental options perfect for experiencing the city’s dynamic atmosphere while enjoying the convenience of nearby attractions and public transportation. With its diverse community and lively surroundings, Near South Side is an ideal destination for those looking to immerse themselves in authentic Chicago life during their visit.

Downtown Chicago

Staying near the heart of the city provides easy access to business districts and vibrant urban life, making it an ideal choice for travelers seeking modern amenities and convenience.

View 1791+ Rentals in Downtown Chicago

South Loop

This area offers a lively atmosphere with numerous cultural attractions and parks, perfect for those wanting to experience the city's dynamic energy just moments from here.

View 372+ Rentals in South Loop

Bronzeville

Known for its rich history and vibrant community, this neighborhood offers a unique blend of heritage and local charm, appealing to visitors eager to explore authentic cultural experiences nearby.

View 100+ Rentals in Bronzeville

Printers Row

For book lovers and history enthusiasts, staying in this historic district places you close to literary landmarks and the area's distinctive architecture, right here in the region.

View 4021+ Rentals in Printers Row

Chicago Museum Campus

Discover a prime location near world-class museums and scenic views, making it an excellent base for cultural exploration within the city’s renowned museum district.

View 3407+ Rentals in Chicago Museum Campus

Prairie District

This neighborhood combines historic significance with modern development, offering a peaceful retreat while remaining close to the city's main attractions.

View 256+ Rentals in Prairie District

Ickes Prairie Homes

Experience a residential area known for its historic homes and tranquil environment, providing a comfortable and authentic stay just outside the bustling core of the city.

View 2027+ Rentals in Ickes Prairie Homes

Best Times to Visit Near South Side

When should you plan your Rentals by Owner stay?

Choosing the right time to vacation here can enhance your experience, as visiting during the area's peak or shoulder seasons allows you to enjoy optimal weather and local events while benefiting from better rental availability through Rent By Owner.

Peak Season Highlights

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Summer (June to August)

During the summer months, you can enjoy the lively atmosphere and warm weather that attracts visitors to the region. This is the ideal time for exploring outdoor activities and experiencing the vibrant local culture.

Average Temperature Daytime: around 80°F (27°C) - Nighttime: about 65°F (18°C)
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Fall (September to November)

The fall season offers pleasant temperatures and stunning foliage, making it an excellent period to explore the area's attractions comfortably while avoiding the peak summer crowds.

Average Temperature Daytime: approximately 70°F (21°C) - Nighttime: roughly 55°F (13°C)

Off-Season Highlights

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Winter (December to February)

During the winter months, cooler temperatures and fewer travelers create a more relaxed atmosphere. It’s a good time to find deals on rentals by owner when visiting this destination.

Average Temperature Daytime: around 35°F (2°C) - Nighttime: about 25°F (-4°C)
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Early Spring (March to May)

In early spring, the region begins to awaken with milder weather, yet visitor numbers are still lower, providing a quieter experience and better rental deals.

Average Temperature Daytime: roughly 55°F (13°C) - Nighttime: about 40°F (4°C)

Weekly Weather Forecast for Near South Side

How to Book Your Near South Side vacation rental

What's our booking process?

Our platform allows you to browse a curated selection of rentals by owner. 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 Near South Side

More Top-Rated Rentals by Owner in Near South Side Area

Common Rentals by Owner Amenities

What amenities can you expect?

Our Rentals by Owner 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 access to outdoor seating areas, perfect for relaxing while taking in the city views.
  • Take advantage of on-site barbecue grills for outdoor dining experiences.
  • Make use of nearby parks and green spaces for leisurely strolls or picnics.
  • Benefit from private patios or balconies that offer a personal outdoor retreat.
  • Explore walking and biking trails conveniently located within the neighborhood.
  • Find outdoor pools available for cooling off during warmer months.
  • Utilize outdoor recreational facilities, such as tennis courts or fitness areas, often included in vacation rentals here.

Top Attractions Around Near South Side

What attractions are nearby?

In this vibrant area, you'll find a variety of nearby activities to enjoy, from exploring cultural landmarks to experiencing local dining options, making your stay both memorable and convenient.

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Family Activities

  • Field Museum of Natural History: Discover fascinating exhibits and interactive displays that make this a must-visit destination for families interested in natural history and culture, conveniently located nearby.
  • Adler Planetarium: Explore the wonders of the universe with engaging shows and activities that captivate children and adults alike, offering an educational experience just moments from your stay.
  • Chicago Children's Museum at Navy Pier: Enjoy hands-on exhibits and family-friendly entertainment at this popular museum situated at Navy Pier, perfect for a fun-filled day with loved ones.
  • Navy Pier Centennial Wheel: Take in breathtaking views of the skyline and lake while riding this iconic Ferris wheel, providing a memorable outing for families visiting the region.
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Adult Activities

  • Art Institute of Chicago: Explore world-class collections and immerse yourself in the vibrant culture just a short distance from your rental.
  • Chicago Architecture River Cruise: Experience the stunning skyline views and learn about the area's renowned architectural history with a relaxing boat tour.
  • Museum Campus: Visit this cultural hub featuring major institutions where you can indulge in art, science, and history exhibits nearby.
  • Pilsen Neighborhood Art Walks: Discover local murals and contemporary art in this lively district that celebrates creative expression right here.

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South Side
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Near South Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining Options: Take time to discover the diverse culinary scene within the area, enhancing your stay by experiencing authentic regional flavors directly around your rental.
  • Plan Convenient Transportation: Utilize nearby public transit or consider bike rentals to easily access key attractions and avoid parking hassles during your visit here.
  • Set Your Itinerary Smartly: Prioritize must-see spots close to your accommodation, allowing you to maximize your time exploring without extensive travel.
  • Engage with the Community: Attend local events or visit neighborhood markets to get a genuine feel for this vibrant destination and enrich your overall experience.

Transportation Options

  • Chicago Transit Authority (CTA) Trains: The CTA rail system offers convenient access to the region, connecting you directly to popular destinations within and beyond the nearby area.
  • Bus Services: Extensive bus routes serve this part of the city, providing flexible transportation options around the clock.
  • Divvy Bike Share: For an eco-friendly and active way to explore here, the bike-sharing program allows easy rentals for short-distance travel around the region.
  • Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft provide quick, reliable transportation when visiting this part of Chicago’s vibrant neighborhood.

Local Customs Options

  • Respect for Local Arts and Cultural Expressions: You’ll find that embracing the area's vibrant arts scene is a key part of engaging with the local community here.
  • Supporting Local Businesses: Shopping at neighborhood boutiques and dining at small eateries demonstrates your appreciation for the region's unique character.
  • Participation in Community Events: Attending festivals and local gatherings offers a meaningful way to connect with the area's traditions and residents.
  • Environmental Consciousness: Practicing eco-friendly habits aligns with the region’s efforts to preserve its urban landscape and green spaces.

Frequently Asked Questions About Near South Side Rentals by Owner

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

There are a lot of options in Near South Side. If you plan on staying in the Near 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 Near South Side:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 425 in the Near 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 Near South Side. 

3. What is the cancellation policy for a rental by owner in Near South Side, Chicago?

The cancellation policy varies depending on the individual listing. To understand the specifics, please review the cancellation terms provided in the rental listing or contact the owner directly before booking.

4. How do I confirm the availability of a rental property by owner in the region?

Availability can be checked through the listing’s real-time calendar on the booking platform. For precise confirmation, reaching out to the owner is recommended to ensure the dates are open.

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

Additional fees, such as cleaning or service charges, are typically detailed in the listing description. Always review these details carefully or contact the owner for clarification before finalizing your reservation.

6. What amenities are usually included in rentals by owner in this area?

Most rentals offer core amenities like Wi-Fi, kitchen facilities, and linens. Specific features vary per property, so it’s best to verify what’s included by reading the listing details or asking the owner directly.

7. What is the check-in process for a rental by owner in near South Side, Chicago?

Check-in procedures are outlined in each listing and may include flexible or scheduled key exchanges. Confirm these details with the owner during the booking process to ensure a smooth arrival.

More Rentals You May Like Near Near South Side

More Top-Rated Rentals by Owner in Near South Side Area