Search Vacation Homes in Northwest Side
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Our top choices for Northwest Side vacation homes
Vacation Home in Belmont Cragin
Game Room • Fire-pit • Playground • Gym • Billiard$416 nightly
The price is $492
Jan 14 - Jan 15, 2026
Total with taxes and fees
Vacation Home in Portage Park
Sleeps 18 • 8BR • Game Room • Gym • Theater$753 nightly
The price is $917
Jan 13 - Jan 14, 2026
Total with taxes and fees
Vacation 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.
$174 nightly
The price is $185
Dec 23 - Dec 24
Total with taxes and fees
Vacation 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.
$309 nightly
The price is $330
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vacation Home in Des Plaines
Getaway Near ORD With Great Local Amenities9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
Stephanie G.
$263 nightly
The price is $278
Dec 22 - Dec 23
Total with taxes and fees
Vacation 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.
$372 nightly
The price is $398
Dec 28 - Dec 29
Total with taxes and fees
Vacation Home in Maywood
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed8.0 out of 10, Very Good, (20)
"Very nice place "
Elliot H.
$222 nightly
The price is $237
Dec 22 - Dec 23
Total with taxes and fees
Vacation 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.
$491 nightly
The price is $562
Jan 20 - Jan 21, 2026
Total with taxes and fees
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
LondonHouse Chicago, Curio Collection by Hilton
10/10 Excellent
Find out more about Northwest Side
Northwest Side Vacation Homes information
Number of reviews | 313 |
|---|---|
Accommodation | 336 Vacation Homes |
Lowest Price | $169 |
Highest Price | $917 |
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