Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop 
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8.5 (81 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Best Price Match 190+ Vacation Rentals Near Near South Side
NearbyHoliday - Vacation Rentals in Near South Side
The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile Best Price Match
9.2 (59 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • In Near South Side · 4.4km to center
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Fulbrix Bright Designer Apartments with West Loop Views Best Price Match
9.5 (50 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near West Side • In Near South Side · 4.5km to center
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Aurelien Spacious Apartments in the Heart of Gold Coast Best Price Match
8.9 (58 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • In Near South Side · 4.5km to center
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K2 Sky High Apartments with Stunning Chicago Views in West Loop Best Price Match
9.5 (24 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
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Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop Best Price Match
8.4 (51 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
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Lux Apts with Lake Views and Top Amenities Best Price Match
9.9 (26 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
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Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena Best Price Match
8.9 (194 Reviews) Apartment
The entire place is yours • 60 m² size • Kitchen
Chicago Near South Side • In Near South Side · 441m to center
Best Price Match Luxury Places to Stay in Near South Side
Over 104+ Luxury Places to Stay in or Near Near South Side
The Peninsula Chicago Best Price Match
9.4 (237 Reviews) Hotel
Breakfast • Indoor swimming pool • 3 restaurants
Chicago Near North Side • In Near South Side · 4.3km to center
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Park Hyatt Chicago Best Price Match
9.2 (89 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near South Side · 4.4km to center
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The Langham Chicago Best Price Match
9.4 (333 Reviews) Hotel
Private parking • Indoor swimming pool • 2 restaurants
Chicago Near North Side • In Near South Side · 3.5km to center
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Waldorf Astoria Chicago Best Price Match
9.5 (137 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near South Side · 4.7km to center
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Four Seasons Chicago Best Price Match
8.7 (145 Reviews) Hotel
Private parking • Indoor swimming pool • Restaurant
Chicago Near North Side • In Near South Side · 4.7km to center
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The Ritz-Carlton, Chicago Best Price Match
8.6 (57 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near South Side · 4.5km to center
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Nobu Hotel Chicago Best Price Match
9.0 (375 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near West Side • In Near South Side · 3.9km to center
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Trump International Hotel & Tower Chicago Best Price Match
9.2 (1287 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near South Side · 3.6km to center
Best Price Match Pet-Friendly Vacation Rentals in Near South Side
Over 95+ Pet-Friendly Vacation Rentals in or Near Near South Side
River Hotel Pets allowed Best Price Match
8.4 (7431 Reviews) Hotel
Breakfast • Pet friendly • Free WiFi
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Club Quarters Hotel Wacker at Michigan, Chicago Pets allowed Best Price Match
8.4 (3172 Reviews) Hotel
Breakfast • Pet friendly • Free WiFi
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Club Quarters Hotel Central Loop, Chicago Pets allowed Best Price Match
8.2 (5405 Reviews) Hotel
Breakfast • Restaurant • Pet friendly
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Central Loop Hotel Pets allowed Best Price Match
8.1 (2990 Reviews) Hotel
Breakfast • Restaurant • Pet friendly
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The Emily Hotel Pets allowed Best Price Match
8.7 (271 Reviews) Hotel
Private parking • 2 restaurants • Pet friendly
Chicago Near West Side • In Near South Side · 4.3km to center
Best Price Match Fulbrix Bright Designer Apartments with West Loop Views Pets allowed Best Price Match
9.5 (50 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near West Side • In Near South Side · 4.5km to center
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Level Chicago Fulton Market Pets allowed Best Price Match
9.1 (123 Reviews) Hotel
Private parking • Outdoor swimming pool • Spa
Chicago Near West Side • In Near South Side · 4.1km to center
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Level Chicago - River North Pets allowed Best Price Match
8.8 (233 Reviews) Hotel
Private parking • Outdoor swimming pool • Pet friendly
Chicago River North • In Near South Side · 4.1km to center
Best Price Match Vacation Rentals in Near South Side
Over 62+ Vacation Rentals in or Near Near South Side
Experience Downtown Chicago at Millennium - Luxury Apartments in The Loop Best Price Match
8.5 (81 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Best Price Match The Bernardin Gold Coast Luxury Apartments Near Magnificent Mile Best Price Match
9.2 (59 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • In Near South Side · 4.4km to center
Best Price Match Fulbrix Bright Designer Apartments with West Loop Views Best Price Match
9.5 (50 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near West Side • In Near South Side · 4.5km to center
Best Price Match Aurelien Spacious Apartments in the Heart of Gold Coast Best Price Match
8.9 (58 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Chicago Near North Side • In Near South Side · 4.5km to center
Best Price Match K2 Sky High Apartments with Stunning Chicago Views in West Loop Best Price Match
9.5 (24 Reviews) Apartment
Apartments • Private parking • Outdoor swimming pool
Best Price Match Linea Luxury Living with Indoor Pool and Rooftop Views in The Loop Best Price Match
8.4 (51 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
Best Price Match Lux Apts with Lake Views and Top Amenities Best Price Match
9.9 (26 Reviews) Apartment
Apartments • Private parking • Indoor swimming pool
Best Price Match Luxéry Stay Chicago - Themed Units! Close to Downtown, McCormick Place & Wintrust Arena Best Price Match
8.9 (194 Reviews) Apartment
The entire place is yours • 60 m² size • Kitchen
Chicago Near South Side • In Near South Side · 441m to center
Best Price Match Villa Places to Stay in Near South Side
Over 1+ Villa Places to Stay in or Near Near South Side
Hamaline Luxury Guest House Best Price Match
8.5 (7 Reviews) Villa
The entire place is yours • 1400 m² size • Free on-site parking
Best Price Match Hotels in Near South Side
Over 128+ Hotels in or Near Near South Side
The Royal Sonesta Chicago River North Best Price Match
8.7 (1468 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near South Side · 3.8km to center
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Sports Illustrated Resorts Chicago Best Price Match
8.6 (1339 Reviews) Hotel
Private parking • Free WiFi • Private bathroom
Best Price Match Club Quarters Hotel Wacker at Michigan, Chicago Best Price Match
8.4 (3172 Reviews) Hotel
Breakfast • Pet friendly • Free WiFi
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Godfrey Hotel Chicago Best Price Match
8.2 (677 Reviews) Hotel
1. Off-site parking • 2 restaurants • Spa
Chicago Near North Side • In Near South Side · 4.3km to center
Best Price Match The Emily Hotel Best Price Match
8.7 (271 Reviews) Hotel
Private parking • 2 restaurants • Pet friendly
Chicago Near West Side • In Near South Side · 4.3km to center
Best Price Match Club Quarters Hotel Central Loop, Chicago Best Price Match
8.2 (5405 Reviews) Hotel
Breakfast • Restaurant • Pet friendly
Best Price Match Cheap Places to Stay in Near South Side
Over 128+ Cheap Places to Stay in or Near Near South Side
Chinatown Hotel Chicago Best Price Match
5.7 (1136 Reviews) Hotel
Free WiFi • View • Private bathroom
Chicago Armour Square • In Near South Side · 1.2km to center
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Best Western Chicago Downtown-River North Best Price Match
7.3 (2033 Reviews) Hotel
Private parking • Indoor swimming pool • Restaurant
Chicago Near North Side • In Near South Side · 4.0km to center
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Hotel Saint Clair - Magnificent Mile Best Price Match
7.9 (3979 Reviews) Hotel
Restaurant • Pet friendly • Free WiFi
Chicago Near North Side • In Near South Side · 4.0km to center
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Aloft Chicago Mag Mile Best Price Match
8.3 (2674 Reviews) Hotel
Private parking • Indoor swimming pool • 2 restaurants
Chicago Near North Side • In Near South Side · 4.0km to center
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Hotel Chicago West Loop, SureStay Collection by Best Western Best Price Match
7.3 (813 Reviews) Hotel
Pet friendly • Free WiFi • Non-smoking rooms
Chicago Near West Side • In Near South Side · 4.6km to center
Best Price Match Club Quarters Hotel Central Loop, Chicago Best Price Match
8.2 (5405 Reviews) Hotel
Breakfast • Restaurant • Pet friendly
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Travelodge by Wyndham Downtown Chicago Best Price Match
7.4 (3168 Reviews) Hotel
Free WiFi • Private bathroom • Non-smoking rooms
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Holiday Inn Express Chicago - Magnificent Mile by IHG Best Price Match
7.7 (430 Reviews) Hotel
Breakfast • Free WiFi • Private bathroom
Chicago Near North Side • In Near South Side · 4.1km to center
Best Price Match About Near South Side Vacation Rentals
Looking for places to stay in Near South Side? Compare top options in Chicago.
With more than 190 Near South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation homes, holiday homes, and other short-term private accommodations, offer top-notch amenities with strong value, giving you comfort and luxury at the same time. Get more value and more room when you stay in Near South Side.
Looking for last-minute deals or the best offers on cottages, condos, private villas, and large vacation homes? NearbyHoliday makes it easy to compare different options with a single click. Looking for a rental by owner with swimming pools, hot tubs, pet-friendly stays, or large-suite comforts? You can compare vacation rentals by owner and other popular Airbnb-style properties in Near South Side. Prices average US $177 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Near 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 Stay Categories in Near South Side
Use These Quick Filters to Find a Vacation Rental in Near South Side
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Near South Side.
Pro Tip: Use the quick filters above to compare vacation rentals, holiday homes, hotels, resorts, cabins, villas, and pet-friendly places to stay in Near South Side. These links help you narrow your search faster, discover short-term rentals with the amenities and pricing that fit your trip, and browse popular stay types before checking availability, last-minute options, and the best deals for your preferred travel style.
Weather in Near South Side
Average temperatures and rainfall by month range to help plan your stay in Near South Side.
Mar - May
Avg High17°C / 62°F
Avg Low6°C / 42°F
Rainfall106 mm / 4.2 in
Jun - Aug
Avg High28°C / 83°F
Avg Low18°C / 65°F
Rainfall90 mm / 3.5 in
Sep - Nov
Avg High18°C / 65°F
Avg Low9°C / 48°F
Rainfall70 mm / 2.7 in
Dec - Feb
Avg High3°C / 38°F
Avg Low-5°C / 22°F
Rainfall62 mm / 2.4 in