South Side Accommodations

House

Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!

10.0

Exceptional

(12 Reviews)

2 Bedrooms 2 Baths 5 Guests 1600 ft²

R11,948/Night 7 Nights - R83,630

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Apartment

Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront

10.0

Exceptional

(4 Reviews)

2 Bedrooms 2 Baths 8 Guests 8611.13 ft²

R7,166/Night 7 Nights - R50,165

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Apartment

Skyline view 3br/2ba family heaven with optional parking

1 Bedroom 1 Bath

R5,547/Night 7 Nights - R38,832

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McCormick Patio skyline view 2b/2b with optional Parking/sleep 6

Price Dropped

Apartment

McCormick Patio skyline view 2b/2b with optional Parking/sleep 6

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 6 Guests 900 ft²

R6,689/Night 7 Nights - R46,818

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Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field

Apartment

Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field

10.0

Exceptional

(3 Reviews)

6 Bedrooms 4 Baths 12 Guests 1851.39 ft²

R18,363/Night 7 Nights - R128,540

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Apartment

McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 6 Guests 950 ft²

R6,664/Night 7 Nights - R46,640

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Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots

Apartment

Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 8 Guests 796.53 ft²

R7,022/Night 7 Nights - R49,162

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Apartment

McCormick Place city view 2br/2ba with optional parking for up to 8 guests

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 8 Guests 950 ft²

R6,504/Night 7 Nights - R45,525

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Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines

Apartment

Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines

10.0

Exceptional

(2 Reviews)

2 Bedrooms 2 Baths 8 Guests 796.53 ft²

R13,216/Night 7 Nights - R92,505

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Apartment

McCormick Place 2b/2b family unit with optional parking for up to 8 guests

10.0

Exceptional

(3 Reviews)

2 Bedrooms 2 Baths 8 Guests 800 ft²

R6,375/Night 7 Nights - R44,620

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Large 4BR Cozy Stay Near Field Museum & McCormick

Apartment

Large 4BR Cozy Stay Near Field Museum & McCormick

10.0

Exceptional

(2 Reviews)

4 Bedrooms 3 Baths 10 Guests 1937.5 ft²

R12,479/Night 7 Nights - R87,364

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New

Apartment

Luxury Studio Apartment Near McCormick Place & Soldier Field

10.0

Exceptional

(3 Reviews)

1 Bedroom 1 Bath 4 Guests 550 ft²

R5,405/Night 7 Nights - R37,830

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More Top-Rated Accommodations in South Side Area

Why Choose Rent By Owner for your South Side Accommodations?

What makes our Accommodations special?

Verified Listings

Book with confidence knowing every property meets our quality and safety standards.

Unbeatable Value

Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.

Diverse Options

From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for South Side

How to Book Your South Side Accommodations

What's our booking process?

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

Booking Steps

Search Properties

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

Select a Rental

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

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Explore and book the perfect rental in South Side

More Top-Rated Accommodations in South Side Area

Common Accommodations Amenities

What amenities can you expect?

Our Accommodations 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

Other Places to Stay in South Side, IL

Frequently Asked Questions about South Side Accommodations

1. What are the top Accommodations 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 Accommodations in South Side:

2. How many Accommodations are available in South Side?

Currently, the total number of properties listed by RBO in 2026 is over 495 in the South Side area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in South Side. 