Trippy Mates - Vacation Rentals in South Side

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba From US $311
         

10.0 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba From US $310
         

10.0 (10 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area From US $792
         

Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area From US $543
         

Luxury Places to Stay in South Side

Over 536+ Luxury Places to Stay in or Near South Side
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 Side

Over 72+ Top-Rated Vacation Rentals with a Pool in or Near South Side
Home2 Suites by Hilton Chicago McCormick Place From US $84
         

|
9.2 (721 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Chicago McCormick Place From US $93
         

|
9.0 (1021 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Home2 Suites By Hilton Chicago McCormick Place From US $258
         

|
8.9 (272 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Homewood Suites by Hilton Chicago Downtown South Loop From US $102
         

|
8.8 (2155 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago Downtown South Loop From US $93
         

|
8.8 (1742 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hilton Garden Inn Chicago McCormick Place From US $88
         

|
8.6 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Hampton Inn Chicago McCormick Place From US $185
         

|
8.4 (788 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in South Side

Over 220+ Pet-Friendly Vacation Rentals in or Near South Side
Safe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba From US $309
         

9.8 (44 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
MICH AVE #23 2bd/2ba Downtown, Museums w/Views From US $289
         

9.8 (28 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
MICH AVE Downtown, Grant Park, Museums #25 2bd/2ba From US $303
         

9.6 (29 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown MICH AVE#4 King Beds |Grant Park, 2bd/2ba From US $299
         

9.4 (26 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pet Friendly
DTown Mich Ave #10 | gym+rooftop w park view From US $189
         

9.4 (13 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Downtown Park #11 - Mich Ave PH | gym+rooftop From US $198
         

9.0 (6 Reviews)
Condo
  • Air Conditioner
  • Pet Friendly
  • TV

Large Vacation Homes & Villas in South Side

Over 69+ Large Vacation Homes & Villas in or Near South Side
McCormick 6B/4Ba Luxury Suite for groups/12 guests From US $669
         

Wheelchair Accessible Vacation Homes in South Side

Over 260+ Wheelchair Accessible Vacation Homes in or Near South Side
Stylish 4BR South Loop Home From US $314
         

10.0 (2 Reviews)
Apartment
  • TV
  • Wheelchair Accessible
  • Accessibility
McCormick 3B/2Ba w optional parking/Up to 8 guests From US $299
         

Downtown 2bd #4 - Near Grant Park, Museums, Lake From US $240
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • TV
  • Wheelchair Accessible

South Side Varoom and Airbnb Places to Stay Under $200

Over 153+ South Side Varoom and Airbnb Places to Stay Under $200
Spacious 2BR Group Retreat Near McCormick Place From US $194
         

SpringHill Suites by Marriott Chicago Chinatown From US $131
         

|
9.6 (1007 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • TV

Instantly Bookable Vacation Homes in South Side

Over 299+ Instantly Bookable Vacation Homes in or Near South Side

About South Side Vacation Rentals

With more than 545 South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Trippymates 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 Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Trippymates South Side, 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 Side. Places to stay near South Side are 898.29 ft² on average, with prices averaging $373 a night.

Trippymates makes it easy and safe to find and compare vacation rentals in South Side 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 Side

Type Count
Holiday Apartments 446
Hotels with Suites 50
Vacation Homes 17

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

Pro Tip: Trippymates makes it easy to compare the best listings on Trippymates homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Trippymates 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 Side.

Weather in South Side

View the weather forecast for South Side before booking your South Side 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