Near North Side holiday homes
We found 1,255 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Near North Side by choosing from 217 houses, 452 apartments and other holiday rentals. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Near North Side
Showing deals for:5 Sept - 12 Sept
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago

9.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
7% off
Price is NZ$13,175
NZ$1,882 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago

9.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$6,843
NZ$978 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.6 out of 10 rating
Exceptional
(8 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$9,501
NZ$1,357 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 01 - Terrace - River North

9.6 out of 10 rating
Exceptional
(10 reviews)
Luxury Loft Collection 01 - Terrace - River North
Chicago, IL
8% off
Price is NZ$15,533
NZ$2,219 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Find properties near top attractions in Near North Side
Map Attractions
Find the best place to stay - Near North Side

Level Chicago – Old Town
Sleeps 8
9.0 out of 10
wonderful
(319 reviews)

Kasa Magnificent Mile Chicago
Sleeps 3 · 1 bedroom
9.2 out of 10
wonderful
(408 reviews)

Sonder by Marriott Bonvoy The Opal Apartments River North
Sleeps 6 · 1 bedroom
8.8 out of 10
excellent
(39 reviews)

Kasa River North Chicago
Sleeps 5 · 2 bedrooms
9.4 out of 10
exceptional
(143 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value