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:

• Cozy Downtown MICH AVE #7 | gym+rooftop
• Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
• Dtown Penthouse 11+Parking, Gym, Pvt Patio
• Downtown 3bd Penthouse| Lake Mich VIEWS +gym
• Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
• Downtown 2bd #4 - Near Grant Park, Museums, Lake
• McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
• Luxury Studio Apartment Near McCormick Place & Soldier Field
• Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
• Bright & Stylish 2BR Family Unit Near McCormick Place & Grant Park

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

• S Loop 1BR w Pool Gym nr Museum Campus CHI-352
• S Loop 2BR w Pool Gym Spa nr Grant Park CHI-740

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:

• Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
• McCormick Place 2b/2b family unit with optional parking for up to 8 guests
• Marriott Marquis Chicago

Currently, the total number of properties listed in 2026 is over 566 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.