Near North Side holiday homes
We found 1,253 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Near North Side by choosing from 221 houses, 446 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:19 Sept - 26 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$10,414
NZ$1,488 per night
includes taxes & fees
Image gallery for Luxury Loft Collection 03 - Terrace - River North

9.2 out of 10 rating
Wonderful
(7 reviews)
Luxury Loft Collection 03 - Terrace - River North
Chicago, IL
7% off
Price is NZ$12,860
NZ$1,837 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago

9.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,022
NZ$432 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago

9.8 out of 10 rating
Exceptional
(17 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$3,724
NZ$532 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Near North Side
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Find the best place to stay - Near North Side

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

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

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

Walk to the Beach! Theater-Coffee Bar-Games-Gym
Sleeps 12 · 4 bedrooms · 2 bathrooms
9.2 out of 10
wonderful
(5 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