Owner Direct Vacation
Rentals 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 Vacation Rentals in South Side:

• MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
• 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
• Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
• Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field
• Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
• McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
• 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
• McCormick 3B/2Ba w optional parking/Up to 8 guests

There are 1 vacation rentals with private pools near South Side. Top-rated homes that have access to a swimming pool include:

• S Loop Studio w Pool Gym Spa nr Grant Park CHI-739

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

• Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
• Stylish 1BR South Loop Unit Near McCormick Place & Wintrust Arena
• Marriott Marquis Chicago

Currently, the total number of properties listed in 2026 is over 524 in the South Side area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Side.