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
• Cozy Downtown MICH AVE #7 | gym+rooftop
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Downtown 3bd Penthouse| Lake Mich VIEWS +gym
• Dtown Penthouse 11+Parking, Gym, Pvt Patio
• Downtown 2bd #4 - Near Grant Park, Museums, Lake
• McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
• McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people
• Luxury Studio Apartment Near McCormick Place & Soldier Field
• Bright & Stylish 2BR Family Unit Near McCormick Place & Grant Park

There are 1 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

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:

• Luxury 3BR Spacious Suite Sleeps 8 Guests with Patio, Skyline View, Optional Parking and Gym Access Near McCormick Place and Lakefront
• Downtown Penthouse - Mich Ave 2bd | +gym & VIEWS
• Best Western Grant Park Hotel

Currently, the total number of properties listed in 2026 is over 581 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.