Discover Your Perfect South Loop Vacation Homes

Best Vacation Homes in South Loop

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South Loop Luxury Rentals

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South Loop Pet Friendly Vacation Rentals

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South Loop 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 South Loop 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 South Loop Vacation Rentals

Where are the best neighborhoods to stay in South Loop?

When exploring the vibrant South Loop neighborhood in Chicago, Illinois, you’ll find a diverse and dynamic area ideal for your stay. Known for its proximity to downtown attractions, South Loop offers convenient access to cultural sites, parks, and entertainment options, making it a great choice for travelers seeking a central location. Whether you’re looking for modern apartment-style vacation rentals or cozy retreats, this neighborhood provides a range of options that combine comfort with accessibility. Enjoy the authentic Chicago experience by choosing a well-situated accommodation in South Loop, ensuring your visit is both memorable and effortless.

Downtown Chicago

Staying in Downtown Chicago places you at the heart of the city's vibrant urban scene, offering easy access to a wide array of dining, shopping, and entertainment options. This area is ideal for those who want to experience the lively atmosphere and cultural attractions of the region.

View 1790+ Rentals in Downtown Chicago

The Loop

The Loop is perfect for visitors seeking convenient proximity to Chicago’s iconic architecture and business hub, with numerous theaters, museums, and parks nearby. Here, you can enjoy the energetic vibe of the city center while having comfortable access to your vacation rentals in this bustling neighborhood.

View 776+ Rentals in The Loop

Near South Side

Located just south of the downtown core, this area's diverse community offers an engaging blend of modern developments and historic charm, making it an excellent choice for exploring Chicago from a central yet relaxed base.

View 360+ Rentals in Near South Side

Printers Row

Known for its literary history and charming streets, Printers Row provides a unique setting for your stay, combining cultural richness with easy access to the rest of the city’s attractions.

View 4021+ Rentals in Printers Row

Chicago Museum Campus

This lakeside destination is ideal for culture enthusiasts who want to indulge in world-class museums and scenic views, all within a convenient distance for your vacation stays.

View 3407+ Rentals in Chicago Museum Campus

Prairie District

The Prairie District offers a peaceful, residential environment with historic landmarks and green spaces, making it a great spot for relaxing after days of exploring the city’s highlights.

View 256+ Rentals in Prairie District

Ickes Prairie Homes

This residential neighborhood provides a quiet retreat with local charm, ideal for travelers wanting a more laid-back experience while still being close to Chicago's main attractions.

View 2027+ Rentals in Ickes Prairie Homes

Best Times to Visit South Loop

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit this vibrant area can enhance your experience, allowing you to enjoy its unique charm at the most comfortable and enjoyable moments of the year.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, you can enjoy warm weather and lively city events, making it an ideal time to explore the area’s vibrant culture and outdoor activities.

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

Early fall offers pleasant temperatures and fewer crowds, perfect for experiencing this destination's scenic beauty and local festivals before the winter season approaches.

Average Temperature Daytime: Between 70°F and 75°F - Nighttime: Around 55°F

Off-Season Highlights

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Winter (December to February)

Winter visitors benefit from lower rates and quieter surroundings, providing a peaceful environment to enjoy the area's indoor attractions and cultural sites.

Average Temperature Daytime: About 30°F - Nighttime: Near 20°F
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Early Spring (March to April)

As the region transitions into spring, you'll find fewer tourists and better deals, with the chance to experience the city's quiet charm before the summer rush begins.

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

Weekly Weather Forecast for South Loop

How to Book Your South Loop 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 Loop

More Top-Rated Vacation Rentals in South Loop 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, perfect for relaxing and taking in the city views.
  • Take advantage of communal outdoor spaces such as courtyards or gardens designed for leisure and socializing.
  • Benefit from on-site outdoor parking facilities to conveniently explore the surrounding area.
  • Utilize outdoor grilling areas or barbecue stations available exclusively for guests’ use.
  • Make the most of nearby parks and green spaces ideal for outdoor activities or picnics during your stay.
  • Access well-maintained walking paths and jogging trails that allow you to explore the neighborhood comfortably.
  • Use outdoor recreational amenities like swimming pools or fitness decks often included in higher-end properties here.

Top Attractions Around South Loop

What attractions are nearby?

Within this vibrant neighborhood, you can enjoy exploring world-class museums, scenic parks, and lively waterfront activities, making your stay here both enriching and entertaining.

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Family Activities

  • Field Museum of Natural History: Explore fascinating exhibits and interactive displays that captivate children and adults alike, making it an engaging day out here.
  • No. 9 Lakefront Trail: Enjoy scenic walks or bike rides along this picturesque trail that offers stunning views of Lake Michigan, perfect for family outings in the area.
  • Adler Planetarium: Discover the wonders of the universe with hands-on exhibits and sky shows designed to inspire curiosity in visitors of all ages.
  • Experience outdoor play areas and public art installations that provide endless entertainment opportunities for families visiting this popular region.
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Adult Activities

  • Art Institute of Chicago: Explore an extensive collection of world-renowned artworks right in the heart of the city, offering a culturally enriching experience during your stay.
  • Maggie Daley Park: Enjoy outdoor relaxation and recreational activities in this urban park, perfect for unwinding after exploring the vibrant neighborhood.
  • Chicago Riverwalk: Take a scenic stroll or a boat tour along the iconic river, immersing yourself in breathtaking views of the city's architecture and skyline.
  • The Field Museum: Delve into fascinating natural history exhibits and immersive displays at a renowned museum conveniently situated near your accommodation here.

Other Places to Stay in South Loop, IL

Pontiac Building
Pontiac Building Vacation Rentals
Mergenthaler Lofts
Mergenthaler Lofts Vacation Rentals
Second Franklin Building
Second Franklin Building Vacation Rentals
Dearborn St Station
Dearborn St Station Vacation Rentals
Printers Row
Printers Row Vacation Rentals
Spertus Institute of Jewish Studies
Spertus Institute of Jewish Studies Vacation Rentals
Columbia College Chicago
Columbia College Chicago Vacation Rentals
Museum of Contemporary Photography
Museum of Contemporary Photography Vacation Rentals
Dearborn Park
Dearborn Park Vacation Rentals
South Side
South Side Vacation Rentals
Near South Side
Near South Side Vacation Rentals
Prairie District
Prairie District Vacation Rentals
More Places to Stay Near South Loop

South Loop Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Transportation in Advance: Take advantage of the area’s public transit options and consider renting a bike or walking to explore nearby attractions comfortably and efficiently.
  • Discover Local Dining Options: Savor diverse culinary experiences by trying out popular restaurants and cafes within walking distance from your vacation rental here.
  • Visit Cultural and Entertainment Venues: Explore the region’s vibrant arts scene and entertainment hubs, ensuring you leave enough time for memorable experiences during your stay.
  • Maximize Your Booking Flexibility: Look for vacation rentals that offer flexible cancellation policies and amenities to customize your visit based on your interests and plans.

Transportation Options

  • Chicago Transit Authority (CTA) Bus System: You can easily access the region's extensive bus network to navigate around the area and reach key attractions conveniently.
  • Chicago 'L' Train Service: The elevated train system offers quick and reliable transit options, connecting you directly to downtown Chicago and beyond from your stay here.
  • Divvy Bike Sharing Program: For an eco-friendly and flexible way to explore the city, this bike-sharing program provides convenient stations throughout the neighborhood.
  • Taxis and Rideshare Services: Easily available in the region, these transportation options allow you to travel comfortably and efficiently to nearby destinations or for late-night returns.

Local Customs Options

  • Chicago-Style Deep-Dish Pizza: You’ll find that sharing a slice of this iconic dish is a beloved local tradition here in the region’s vibrant food scene.
  • Fairs and Festivals: Participating in community events like the annual neighborhood festivals allows you to experience the area’s lively spirit firsthand.
  • Architectural Tours: Appreciating the skyline with guided tours showcases the region’s rich architectural heritage and innovative designs.
  • Sports Enthusiasm: Cheering for local teams during games highlights the passionate sports culture that’s deeply rooted in the city’s identity.

Frequently Asked Questions About South Loop?

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

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

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

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

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

If you are looking for a family-friendly vacation home in South Loop, 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 Loop:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 497 in the South Loop 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 Loop. 

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

Cancellation policies vary by property, so it’s important to review the specific listing details or contact the owner directly to understand the terms and any potential fees involved.

6. Are there any minimum stay requirements for booking here?

Minimum stay requirements depend on the individual property. Please check the listing information or reach out to the owner for specifics regarding length of stay and any restrictions.

7. How do I find available vacation rentals in this region during my travel dates?

You can easily search for available options by entering your desired travel dates into the booking platform and filtering results based on your preferences for location, amenities, and price.

8. What amenities are typically included in vacation rentals in this destination?

Amenities vary between properties but often include essentials such as Wi-Fi, kitchen facilities, and laundry options. For detailed information, review each listing or contact the owner directly.

9. Is there a secure process for payment and communication during the booking?

Yes, the platform ensures a secure payment system and provides messaging tools that allow you to communicate safely with property owners before completing your reservation.