Discover Your Perfect Southwest Side Vacation Homes

Southwest Side Luxury Rentals

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Southwest Side Pet Friendly Vacation Rentals

5.0 (832 Reviews)
Hotel
Carlton Inn Midway
  • Air Conditioner
  • Parking
  • Pet Friendly
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6.0 (2 Reviews)
Apartment
Cozy Spacious 3br
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
View Availability
See More Pet-Friendly Vacation Rentals in Southwest Side on PetFriendly.io

Why Choose Rent By Owner for your Southwest 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 Southwest Side Vacation Rentals

Where are the best neighborhoods to stay in Southwest Side?

When exploring Southwest Side, Illinois, you will find a variety of neighborhoods that cater to different preferences and lifestyles. Each area offers unique character, making it easy to find the perfect place to stay during your visit. Whether you're seeking vibrant community atmospheres or quieter residential streets, Southwest Side provides a range of options for comfortable and convenient accommodation. By choosing the right neighborhood, you can enhance your experience and enjoy everything this charming region has to offer.

Englewood

Situated within the Southwest Side area, this neighborhood offers accessible vacation rentals for travelers seeking an authentic Chicago experience. Here, you can enjoy a variety of locally rooted accommodations that provide comfort and convenience.

View 335+ Rentals in Englewood

Archer Heights

This part of the region is known for its welcoming community and a range of well-appointed vacation rentals. Staying here places you close to key city attractions while offering a peaceful retreat.

View 109+ Rentals in Archer Heights

Chicago Lawn

A vibrant neighborhood in the southwest, it features diverse accommodation options perfect for travelers looking to explore the area's rich culture from a comfortable base.

View 95+ Rentals in Chicago Lawn

Ashburn

Known for its friendly atmosphere, Ashburn provides a selection of cozy vacation rentals that are ideal for families or solo explorers seeking a genuine local experience.

View 109+ Rentals in Ashburn

Clearing

This neighborhood offers convenient access to various amenities and a variety of vacation rental options suitable for those wanting to stay in a friendly, accessible part of the city.

View 126+ Rentals in Clearing

Sleepy Hollow

Offering a quieter environment within the Southwest Side, Sleepy Hollow features well-maintained vacation rentals perfect for visitors seeking tranquility while remaining close to city attractions.

View 118+ Rentals in Sleepy Hollow

Canaryville

A lively area with a wide selection of vacation rentals that cater to travelers interested in experiencing local culture and easy access to the broader city.

View 888+ Rentals in Canaryville

Bridgeport

This historic neighborhood boasts unique vacation rental options and a rich local heritage, making it a compelling choice for those eager to immerse themselves in the area's authentic charm.

View 1353+ Rentals in Bridgeport

Best Times to Visit Southwest Side

When should you plan your Vacation Rentals stay?

Timing your visit to this destination can enhance your experience, so consider the local climate and peak seasons to find the perfect moment for booking your vacation rentals here in Southwest Side, Illinois.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this destination experiences its highest influx of visitors, making it an ideal time if you want to enjoy warm weather and lively local events in the area.

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

Early fall offers pleasant weather and beautiful foliage, attracting travelers seeking scenic views and comfortable outdoor activities in this region.

Average Temperature Daytime: around 75°F - Nighttime: around 50°F

Off-Season Highlights

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Winter (December to February)

Winters tend to be quieter with fewer visitors, providing a peaceful retreat for those looking to explore without the crowds, while enjoying the cooler temperatures.

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

Spring sees a slowdown before the peak summer season, offering a quieter experience while the landscape begins to bloom and temperatures moderate.

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

Weekly Weather Forecast for Southwest Side

How to Book Your Southwest 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 Southwest Side

More Top-Rated Vacation Rentals in Southwest 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 deck to unwind and relax in the fresh air.
  • Take advantage of spacious yards ideal for outdoor activities or gatherings.
  • Make the most of nearby parks and green spaces to explore nature during your stay.
  • Relax by an outdoor swimming pool available at select properties in the area.
  • Utilize outdoor dining areas perfect for enjoying meals under the open sky.
  • Benefit from easy access to walking or biking trails that showcase the region’s natural beauty.
  • Some rentals feature outdoor fireplaces or fire pits for cozy evenings outdoors.

Top Attractions Around Southwest Side

What attractions are nearby?

Within this vibrant region, you can explore a variety of outdoor parks, cultural landmarks, and local dining experiences that showcase the best of Southwest Side, Illinois, USA, making it an ideal destination to enjoy your stay in nearby vacation rentals.

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Family Activities

  • Chicago Lawn Park & Recreation Center: Enjoy outdoor activities and family-friendly amenities in this local community hub, perfect for a relaxing day out.
  • The Midway Plaisance Park: Discover scenic walking paths and open green spaces, ideal for picnics and recreational fun for all ages.
  • Chicago Ridge Mall: Experience a variety of shopping, dining, and entertainment options that cater to families seeking leisure and convenience in the area.
  • Local Cultural Festivals: Participate in vibrant community events that showcase regional traditions and offer engaging entertainment for your family during your stay.
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Adult Activities

  • Explore the Field Museum of Natural History: Dive into fascinating exhibits and discover the region's natural and cultural history, all accessible from your accommodation in this vibrant area.
  • Visit the Shedd Aquarium: Experience marine life up close at one of the world's largest indoor aquariums, just a short trip away in the city's renowned waterfront district.
  • Stroll through Millennium Park: Enjoy outdoor art installations, gardens, and iconic landmarks like the Cloud Gate sculpture within easy reach of your stay here.
  • Enjoy a Chicago River Architecture Cruise: Take a relaxing boat tour to admire the stunning skyline and learn about the area's architectural heritage from the water.

Other Places to Stay in Southwest Side, IL

Canaryville
Canaryville Vacation Rentals
McKinley Park
McKinley Park Vacation Rentals
Ducktown
Ducktown Vacation Rentals
Englewood
Englewood Vacation Rentals
New City
New City Vacation Rentals
Back of the Yards
Back of the Yards Vacation Rentals
Brighton Park
Brighton Park Vacation Rentals
Garfield Ridge
Garfield Ridge Vacation Rentals
Archer Heights
Archer Heights Vacation Rentals
West Lawn
West Lawn Vacation Rentals
Chicago Lawn
Chicago Lawn Vacation Rentals
Gage Park
Gage Park Vacation Rentals
More Places to Stay Near Southwest Side

Southwest Side Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Transportation: Arrange convenient transportation options ahead of time to explore the area efficiently and make the most of your stay near this vibrant destination.
  • Discover Local Cuisine: Take the opportunity to savor regional flavors by visiting local eateries, enhancing your experience in this culturally rich part of the region.
  • Prioritize Nearby Attractions: Identify key attractions close to your vacation rentals to maximize sightseeing without lengthy travel times within this diverse area.
  • Stay Flexible with Your Schedule: Keep your itinerary adaptable to enjoy spontaneous experiences that truly capture the essence of this lively region.

Transportation Options

  • Chicago Transit Authority (CTA) Bus and Rail System: You can rely on the extensive network of buses and trains that connect this region to downtown Chicago and surrounding neighborhoods, offering convenient transportation options during your stay.
  • Metra Commuter Rail: This commuter rail service provides quick access to the city center and beyond, making it ideal for exploring urban attractions from your nearby accommodation.
  • Taxis and Rideshare Services: Taxis and popular rideshare options like Uber and Lyft are readily available here, providing flexible and on-demand transportation around the region.
  • Personal Vehicles: If you prefer driving, renting a car offers the freedom to explore the area's diverse attractions and destinations at your own pace.

Local Customs Options

  • Respect for Local Heritage: Understand that the area values its rich history and traditions, so showing appreciation for local customs is highly encouraged.
  • Cultural Celebrations: Participate in community festivals and events that celebrate the region’s unique heritage, offering an authentic experience during your stay.
  • Dining Etiquette: When dining at local establishments, observe customary manners and be open to trying regional specialties to fully enjoy this destination’s culinary culture.
  • Community Engagement: Engage with residents respectfully and attentively, as fostering good relationships enhances your experience in the region’s welcoming environment.

Frequently Asked Questions About Southwest Side?

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

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

2. Which vacation homes in Southwest Side are best for families?

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

3. How many Rentbyowner vacation rentals are available in Southwest Side?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 93 in the Southwest 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 Southwest Side. 

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

Cancellation policies vary by property; you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

5. Are there any additional fees I should be aware of when booking in this region?

Additional fees such as cleaning, service charges, or security deposits are typically detailed in the listing. It's best to review these details before finalizing your reservation or reach out to the host for clarification.

6. How do I confirm the availability of a vacation rental in this destination?

Availability can be confirmed through the listing calendar on the property page. If you have questions about dates or availability, contacting the owner can help ensure your preferred dates are secured.

7. What amenities are usually included in vacation rentals here?

Amenities vary by property but often include essentials like Wi-Fi, parking, and kitchen facilities. For specific amenities, please check the individual listing or contact the host directly.

8. What should I know about checking in and out of vacation rentals in this area?

Check-in and check-out procedures are outlined in each listing, but they can differ. Confirm the details with the property owner to ensure a smooth arrival and departure process.