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 114+ Vacation Rentals Near Near North Side
NearbyHoliday - Vacation Rentals in Near North 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 North Side · 656m 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 North Side · 2.7km 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 North Side · 312m 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 
4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome Best Price Match
9.6 (5 Reviews) Holiday_home
The entire place is yours • 279 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 920m to center
Best Price Match 
5 Bedroom Huge House in Best Location Parking Fireplace Back Yard Best Price Match
8.3 (3 Reviews) Holiday_home
The entire place is yours • 279 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 1.0km to center
Best Price Match 
Designer Themed 4 Bedroom in Best Location with Patio and Fireplace Best Price Match
9.7 (26 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 920m to center
Best Price Match Luxury Places to Stay in Near North Side
Over 70+ Luxury Places to Stay in or Near Near North Side
The Peninsula Chicago Best Price Match
9.4 (237 Reviews) Hotel
Breakfast • Indoor swimming pool • 3 restaurants
Chicago Near North Side • In Near North Side · 789m to center
Best Price Match 
Park Hyatt Chicago Best Price Match
9.2 (89 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near North Side · 740m to center
Best Price Match 
The Langham Chicago Best Price Match
9.4 (333 Reviews) Hotel
Private parking • Indoor swimming pool • 2 restaurants
Chicago Near North Side • In Near North Side · 1.3km to center
Best Price Match 
Waldorf Astoria Chicago Best Price Match
9.5 (137 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near North Side · 460m to center
Best Price Match 
Four Seasons Chicago Best Price Match
8.7 (145 Reviews) Hotel
Private parking • Indoor swimming pool • Restaurant
Chicago Near North Side • In Near North Side · 674m to center
Best Price Match 
The Ritz-Carlton, Chicago Best Price Match
8.6 (57 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near North Side · 926m to center
Best Price Match 
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 North Side · 1.3km to center
Best Price Match 
The Penthouse at Grand Plaza Best Price Match
9.3 (114 Reviews) Aparthotel
Apartments • On-site parking • Outdoor swimming pool
Chicago Near North Side • In Near North Side · 939m to center
Best Price Match Pet-Friendly Vacation Rentals in Near North Side
Over 48+ Pet-Friendly Vacation Rentals in or Near Near North Side
Level Chicago - Old Town Pets allowed Best Price Match
9.1 (297 Reviews) Hotel
Private parking • Outdoor swimming pool • Spa
Chicago Near North Side • In Near North Side · 426m to center
Best Price Match 
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 North Side · 992m 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 North Side · 2.7km to center
Best Price Match Designer Themed 4 Bedroom in Best Location with Patio and Fireplace Pets allowed Best Price Match
9.7 (26 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 920m to center
Best Price Match 
Viceroy Chicago Pets allowed Best Price Match
8.9 (1047 Reviews) Hotel
Private parking • Outdoor swimming pool • 2 restaurants
Chicago Near North Side • In Near North Side · 514m to center
Best Price Match 
Sofitel Chicago Magnificent Mile Pets allowed Best Price Match
8.8 (1253 Reviews) Hotel
Breakfast • On-site parking • Restaurant
Chicago Near North Side • In Near North Side · 523m to center
Best Price Match Trump International Hotel & Tower Chicago Pets allowed Best Price Match
9.2 (1287 Reviews) Hotel
Breakfast • Private parking • Indoor swimming pool
Chicago Near North Side • In Near North Side · 1.3km to center
Best Price Match 
Kinzie Hotel Pets allowed Best Price Match
8.8 (1192 Reviews) Hotel
Breakfast • Private parking • Pet friendly
Chicago Near North Side • In Near North Side · 1.2km to center
Best Price Match Vacation Rentals in Near North Side
Over 38+ Vacation Rentals in or Near Near North 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 North Side · 656m 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 North Side · 2.7km 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 North Side · 312m 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 4 Bedroom Home in Best Location Parking Fireplace Back Yard Pets Welcome Best Price Match
9.6 (5 Reviews) Holiday_home
The entire place is yours • 279 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 920m to center
Best Price Match 5 Bedroom Huge House in Best Location Parking Fireplace Back Yard Best Price Match
8.3 (3 Reviews) Holiday_home
The entire place is yours • 279 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 1.0km to center
Best Price Match Designer Themed 4 Bedroom in Best Location with Patio and Fireplace Best Price Match
9.7 (26 Reviews) Holiday_home
The entire place is yours • 139 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 920m to center
Best Price Match Resorts in Near North Side
Over 1+ Resorts in or Near Near North Side
The Hotel & Athletic Club at Midtown Best Price Match
8.9 (170 Reviews) Resort
Free on-site parking • 2 swimming pools • Restaurant
Chicago Wrigley Field • In Near North Side · 4.8km to center
Best Price Match Villa Places to Stay in Near North Side
Over 1+ Villa Places to Stay in or Near Near North Side
Luxurious Gold Coast 4BR 4-Story Villa with Parking Sleeps 12 Guests Best Price Match
9.2 (8 Reviews) Villa
The entire place is yours • 274 m² size • Free on-site parking
Chicago Near North Side • In Near North Side · 398m to center
Best Price Match Hotels in Near North Side
Over 75+ Hotels in or Near Near North 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 North Side · 1.0km to center
Best Price Match 
Godfrey Hotel Chicago Best Price Match
8.2 (677 Reviews) Hotel
1. Off-site parking • 2 restaurants • Spa
Chicago Near North Side • In Near North Side · 538m to center
Best Price Match Level Chicago - Old Town Best Price Match
9.1 (297 Reviews) Hotel
Private parking • Outdoor swimming pool • Spa
Chicago Near North Side • In Near North Side · 426m to center
Best Price Match Level Chicago - River North Best Price Match
8.8 (233 Reviews) Hotel
Private parking • Outdoor swimming pool • Pet friendly
Chicago River North • In Near North Side · 992m to center
Best Price Match 
Riu Plaza Chicago Best Price Match
9.2 (7106 Reviews) Hotel
Breakfast • Free WiFi • Private bathroom
Chicago Near North Side • In Near North Side · 1.1km to center
Best Price Match 
Sable At Navy Pier Chicago, Curio Collection By Hilton Best Price Match
9.0 (1018 Reviews) Hotel
Breakfast • On-site parking • 2 restaurants
Chicago Near North Side • In Near North Side · 2.6km to center
Best Price Match 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 North Side · 1.3km to center
Best Price Match Viceroy Chicago Best Price Match
8.9 (1047 Reviews) Hotel
Private parking • Outdoor swimming pool • 2 restaurants
Chicago Near North Side • In Near North Side · 514m to center
Best Price Match About Near North Side Vacation Rentals
Looking for places to stay in Near North Side? Compare top options in Chicago.
With more than 114 Near North 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 North 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 North Side. Prices average US $271 a night.
NearbyHoliday makes it easy and safe to find and compare vacation rentals in Near North 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 North Side
Use These Quick Filters to Find a Vacation Rental in Near North Side
Browse the most useful filters to narrow down vacation rentals, holiday homes, and other places to stay in Near North 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 North 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 North Side
Average temperatures and rainfall by month range to help plan your stay in Near North 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