Holiday Homes in Northwest Side
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Our top choices for Northwest Side holiday homes
Holiday Home in Belmont Cragin
Game Room • Fire-pit • Playground • Gym • BilliardThe price is NZ$847
includes taxes & fees
14 Jan - 15 Jan 2026
Holiday Home in Portage Park
Sleeps 18 • 8BR • Game Room • Gym • TheaterThe price is NZ$1,552
includes taxes & fees
7 Jan - 8 Jan 2026
Holiday Home in Riverwoods
Master qtr close to nature & easy urban facilities9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
Joshua K.
The price is NZ$333
includes taxes & fees
5 Jan - 6 Jan 2026
Holiday Home in Worth
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is NZ$579
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Willow Springs
Coziest estate home 20 minutes to downtown8.8 out of 10, Excellent, (16)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
Gabriela N.
The price is NZ$682
includes taxes & fees
29 Dec - 30 Dec
Holiday Home in La Grange Highlands
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
Arnie B.
The price is NZ$463
includes taxes & fees
30 Dec - 31 Dec
Holiday Home in Westchester
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!9.8 out of 10, Exceptional, (19)
"Great place Great location "
Josh W.
The price is NZ$827
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Home in Oak Park
Vintage Urban Retreat10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
Thomas P.
The price is NZ$876
includes taxes & fees
5 Jan - 6 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Northwest Side Hotel Reviews
Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
Find out more about Northwest Side
Northwest Side Holiday Homes information
Number of reviews | 362 |
|---|---|
Accommodation | 336 Holiday Homes |
Lowest Price | NZ$333 |
Highest Price | NZ$1,552 |
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