Owner Direct 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:

• MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Dtown Penthouse 11+Parking, Gym, Pvt Patio, Pool
• 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 3B/2Ba w optional parking/Up to 8 guests
• McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
• 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct

There are 2 vacation rentals with private pools near South Loop. Top-rated homes that have access to a swimming pool include:

• S Loop Studio w Pool Gym Spa nr Grant Park CHI-739
• Hilton Garden Inn Chicago McCormick Place

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:

• Modern and Bright 2BR on Michigan Ave with Optional Parking and Gym Access Near Soldier Field & Grant Park
• Stylish 1BR South Loop Unit Near McCormick Place & Wintrust Arena
• The Wheeler Mansion

Currently, the total number of properties listed in 2026 is over 535 in the South Loop area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in South Loop.