Discover Your Perfect Near South Side Vacation Homes

Best Vacation Homes in Near South Side

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Near South Side Luxury Rentals

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Near South Side Pet Friendly Vacation Rentals

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Near South Side Large Vacation Homes

7.2 (7 Reviews)
Apartment
South Loop 2 Bedroom Apt
  • Air Conditioner
  • TV
  • Security/Safety
View Availability
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Why Choose Rent By Owner for your Near South Side Vacation Rental Homes?

What makes our Vacation Rentals 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 Vacation Rentals

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

When considering where to stay near South Side Chicago, Illinois, you’ll find that this vibrant neighborhood offers a diverse range of options for your getaway. The area’s convenient location provides easy access to the city’s cultural and entertainment hubs, making it an ideal choice for travelers seeking an authentic Chicago experience. Whether you're looking for modern apartments or cozy homes, the neighborhood's vacation rentals offer comfort and convenience in a lively urban setting. Booking your stay in this part of Chicago ensures you’re close to key attractions while enjoying the unique atmosphere that South Side has to offer.

Downtown Chicago

Located at the heart of the city, Downtown Chicago offers easy access to iconic landmarks and vibrant urban life, making it an ideal base for exploring this bustling region. Staying here provides convenience and a true city experience, perfect for those seeking proximity to major attractions.

View 1753+ Rentals in Downtown Chicago

South Loop

This neighborhood is known for its blend of cultural sites and lively atmosphere, offering a comfortable stay close to the region's key museums and parks. It’s a popular choice for visitors wanting to immerse themselves in Chicago’s dynamic downtown energy.

View 372+ Rentals in South Loop

Bronzeville

Rich in history and community charm, this area invites you to experience local culture while enjoying convenient access to the region’s notable sites. Here, you can combine authentic neighborhood charm with easy reach to central Chicago activities.

View 100+ Rentals in Bronzeville

Printers Row

Known for its literary and historic ambiance, this district offers a unique stay with its charming streets and cultural flair, placing you close to the region’s lively arts scene. Choosing accommodations here puts you within walking distance of many local attractions.

View 4021+ Rentals in Printers Row

Chicago Museum Campus

Ideal for culture enthusiasts, this area surrounds some of the city’s most renowned museums and attractions, providing an enriching stay. It’s a perfect location to explore the region’s educational and cultural offerings.

View 3407+ Rentals in Chicago Museum Campus

Prairie District

Offering a peaceful retreat amidst historic architecture, this neighborhood balances tranquility with proximity to the city’s vibrant downtown scene. It’s well-suited for those looking to enjoy a relaxing yet accessible stay in the region.

View 256+ Rentals in Prairie District

Ickes Prairie Homes

This residential area provides a quiet setting for travelers seeking comfort and local charm, with convenient access to the city’s main attractions. It’s an excellent choice for a peaceful yet connected stay here in the region.

View 2027+ Rentals in Ickes Prairie Homes

Best Times to Visit Near South Side

When should you plan your Vacation Rentals stay?

Choosing the optimal time to visit here can enhance your experience and help you enjoy the vibrant atmosphere of the region while securing the best deals on vacation rentals.

Peak Season Highlights

summer
Late Spring to Early Summer (May - June)

During this period, the area comes alive with vibrant events and a lively atmosphere, making it ideal for exploring local attractions and enjoying warm weather.

Average Temperature Daytime: 70°F to 80°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September - October)

The early fall months offer pleasant weather and fewer crowds, perfect for immersing yourself in the region's cultural activities while experiencing comfortable temperatures.

Average Temperature Daytime: 65°F to 75°F - Nighttime: 50°F to 60°F

Off-Season Highlights

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Winter (December - February)

This time of year tends to be quieter, allowing you to enjoy the area's indoor attractions and cozy accommodations without the peak season crowds.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
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Late Fall (November)

As the weather cools down, you'll find fewer visitors, offering a peaceful experience while taking advantage of lower rates on vacation rentals in the region.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 45°F

Weekly Weather Forecast for Near South Side

How to Book Your Near 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 Near South Side

More Top-Rated Vacation Rentals in Near 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 access to a private outdoor patio or balcony to unwind outside in the fresh air.
  • Take advantage of lush communal gardens or green spaces commonly found in the area for relaxing strolls.
  • Make the most of on-site barbecue grills perfect for outdoor dining with friends or family.
  • Look for properties offering secure, designated parking spaces with easy outdoor access.
  • Stay active with outdoor fitness equipment or nearby running trails available here.
  • Relax by the property’s outdoor seating areas designed for socializing or quiet mornings.
  • Discover nearby parks and open spaces that provide excellent options for picnics and outdoor activities.

Top Attractions Around Near South Side

What attractions are nearby?

In this vibrant area, you can enjoy a variety of nearby activities such as exploring local museums, dining at diverse restaurants, and taking scenic walks along the waterfront, all conveniently accessible from your vacation rental in Near South Side, Chicago.

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Family Activities

  • Field Museum of Natural History: Explore fascinating exhibits and engaging educational experiences perfect for curious families visiting the area.
  • Adler Planetarium: Discover stars and planets through interactive shows and displays, offering an inspiring outing for all ages in this destination.
  • Grant Park: Enjoy outdoor activities, picnics, and scenic views in the region’s iconic green space suitable for family fun and relaxation.
  • Chicago Children's Museum at Navy Pier: Participate in hands-on exhibits and interactive play areas designed to entertain and educate children in the nearby region.
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Adult Activities

  • Art Institute of Chicago: Immerse yourself in world-renowned artworks and exhibits, perfect for enriching your visit to this vibrant part of the city.
  • Maggie Daley Park: Enjoy outdoor activities and scenic views in this urban park, offering a relaxing escape within the bustling neighborhood.
  • Willis Tower Skydeck: Experience breathtaking panoramic views from the iconic skyscraper, an essential activity when exploring the area’s architectural marvels.
  • Chicago Riverwalk: Take a leisurely stroll or dine along the scenic waterway that highlights the region's stunning skyline and lively atmosphere.

Other Places to Stay in Near South Side, IL

Dearborn Park
Dearborn Park 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
National Vietnam Veterans Art Museum
National Vietnam Veterans Art Museum Vacation Rentals
Soldier Field
Soldier Field Vacation Rentals
Glessner House Museum
Glessner House Museum Vacation Rentals
Copernicus Statue
Copernicus Statue Vacation Rentals
William K Kimball House
William K Kimball House Vacation Rentals
South Side
South Side Vacation Rentals
South Loop
South Loop Vacation Rentals
Prairie District
Prairie District Vacation Rentals
More Places to Stay Near Near South Side

Near South Side Travel Tips

How Can You Make the Most of Your Stay?

  • Explore local dining and entertainment options: Take advantage of the vibrant culinary scene and cultural venues nearby to fully experience the area's unique atmosphere during your stay.
  • Plan ahead for transportation: Utilize public transit or consider walking to easily navigate the region’s attractions and avoid parking hassles in this bustling neighborhood.
  • Visit popular landmarks early in the day: Arriving early will help you beat the crowds and enjoy the best of what this destination has to offer at a relaxed pace.
  • Customize your accommodations: Choose vacation rentals that are strategically located to give you convenient access to the area's key sights and local hotspots.

Transportation Options

  • Chicago Transit Authority (CTA) Trains: The CTA's 'L' train system offers convenient access to key areas in the city, making it easy for you to explore the region from your near South Side accommodation.
  • Bus Services: Extensive bus routes connect the neighborhood to downtown Chicago and surrounding districts, providing reliable transportation options during your stay.
  • Divvy Bike Share: The city's bike-sharing program allows you to explore this destination at your own pace with numerous stations conveniently located nearby.
  • Rideshare Services: Popular ride-hailing apps like Uber and Lyft operate seamlessly here, offering flexible, on-demand transportation around the region.

Local Customs Options

  • Respect for Local History: Appreciating the area's rich industrial and cultural heritage is important when engaging with the community here.
  • Support for Local Artists: Visiting art galleries and street murals reflects the region’s vibrant artistic spirit and reinforces your connection to the local culture.
  • Community Engagement: Participating in neighborhood events or supporting small businesses demonstrates your respect for the area’s close-knit community traditions.
  • Environmental Awareness: Practicing eco-friendly habits, such as recycling and conserving energy, aligns with the city’s efforts to preserve this dynamic urban landscape.

Frequently Asked Questions About Near South Side?

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 vacation rentals have private pools in Near South Side?

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

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

If you are looking for a family-friendly vacation home in Near 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 Near South Side:

4. 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 479 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. 

5. What is the cancellation policy for booking a vacation rental in this area?

The cancellation policy varies depending on the property listing. You should review the specific terms provided on the listing page or contact the property owner directly to understand the details and any potential fees.

6. How do I know if a vacation rental in this destination is available for my travel dates?

Availability is listed on each vacation rental's profile. If your preferred dates are not shown as available, you can often reach out to the owner for further assistance or check alternative listings in the region.

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

Additional fees such as cleaning fees, service charges, or taxes are typically outlined in the rental listing. It's advisable to read the full breakdown of costs before finalizing your booking or contact the owner for clarification.

8. What amenities are generally included in vacation rentals in this part of the city?

Most properties offer amenities like Wi-Fi, kitchen facilities, and laundry options, but the exact offerings vary. Review each listing carefully to ensure it meets your needs, and contact the owner if you have specific requirements.

9. How close are vacation rentals here to local attractions and transportation options?

Many rentals are conveniently located near key transit routes and local points of interest. To determine proximity, check the property’s location details on the listing or ask the owner for guidance on public transportation and walking distance to popular sites.

Near South Side Top Rated Vacation Rentals

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