Owner Direct Vacation Rentals in South Loop

The Best Owner Direct Vacation Rentals in South Loop. Explore thousands of vacation home rentals, large cabins, and villas near South Loop

Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

6.0 (1 Review)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Hyatt Regency McCormick Place Chicago From US $228
         

|
9.2 (1056 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Budget-Friendly Room| Free Coffee | Downtown
New
From US $84
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $76
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Luxury Places to Stay in South Loop

Over 513+ Luxury Places to Stay in or Near South Loop
South Loop 2 Bedroom Apt From US $2,671
         

New
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Hyatt Regency McCormick Place Chicago From US $1,495
         

|
8.3 (813 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Wheelchair Accessible
3BR/2BA Luxury Glass Apartment | Amazing Views From US $1,232
         

9.2 (48 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Wheelchair Accessible

Top-Rated Vacation Rentals with a Pool in South Loop

Over 74+ Top-Rated Vacation Rentals with a Pool in or Near South Loop
Downtown Penthouse Lake Views #1|Gym, Parking+Pool From US $391
         

10.0 (4 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Home2 Suites by Hilton Chicago McCormick Place From US $89
         

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9.2 (760 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Chicago McCormick Place From US $95
         

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9.0 (1015 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Home2 Suites By Hilton Chicago McCormick Place From US $258
         

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8.9 (275 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites by Hilton Chicago Downtown South Loop From US $95
         

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8.8 (2191 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago Downtown South Loop From US $89
         

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8.8 (1812 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago McCormick Place From US $93
         

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8.6 (1004 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in South Loop

Over 211+ Pet-Friendly Vacation Rentals in or Near South Loop
MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $320
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish 3BR Gem in Prime Location From US $441
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • View
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $313
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area From US $543
         

Large Vacation Homes & Villas in South Loop

Over 59+ Large Vacation Homes & Villas in or Near South Loop
South Loop 2 Bedroom Apt From US $201
         

8.0 (14 Reviews)
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Luxurious HUGE Penthouse with 4000+ Games, Arcades From US $634
         

McCormick 6B/4Ba Luxury Suite for groups/12 guests From US $657
         

Wheelchair Accessible Vacation Homes in South Loop

Over 282+ Wheelchair Accessible Vacation Homes in or Near South Loop
Modern 3BR Near McCormick & South Loop From US $351
         

|
10.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Marriott Marquis Chicago From US $245
         

|
9.2 (1001 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Spacious 3BR Urban Getaway w Gym From US $441
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Wheelchair Accessible
Downtown 2bd #4 - Near Grant Park, Museums, Lake From US $230
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Marriott Marquis Chicago From US $446
         

|
8.4 (325 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Homewood Suites By Hilton Chicago Downtown South Loop From US $131
         

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8.0 (722 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

South Loop Varoom and Airbnb Places to Stay Under $200

Over 151+ South Loop Varoom and Airbnb Places to Stay Under $200
Budget-Friendly Room| Free Coffee | Downtown
New
From US $76
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Best Western Grant Park Hotel From US $83
         

8.2 (2679 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV
Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

Instantly Bookable Vacation Homes in South Loop

Over 327+ Instantly Bookable Vacation Homes in or Near South Loop
Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $75
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $74
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $73
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety
Budget-Friendly Room| Free Coffee | Downtown
New
From US $73
         

New
Apartment
  • Air Conditioner
  • TV
  • Security/Safety

About South Loop Vacation Rentals

With more than 522 South Loop vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Ownerdirect and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in South Loop.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Ownerdirect South Loop, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in South Loop. Places to stay near South Loop are 904.22 ft² on average, with prices averaging $363 a night.

Ownerdirect makes it easy and safe to find and compare vacation rentals in South Loop with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in South Loop

Type Count
Holiday Apartments 433
Hotels with Suites 44
Vacation Homes 16

Use these Quick Filters to Find a Vacation Rental in South Loop

Pro Tip: Ownerdirect makes it easy to compare the best listings on Ownerdirect homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Ownerdirect homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in South Loop.

Weather in South Loop

View the weather forecast for South Loop before booking your South Loop Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F