Search Vacation Homes in Northwest Side

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Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Northwest Side vacation homes

4 bedrooms, iron/ironing board, travel crib, WiFi
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

Theater • Game Room • Gym • Firepit • 4BR Home
2.0 star property
$449 nightly
The price is $546
Jan 5 - Jan 6, 2026
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
8 bedrooms, iron/ironing board, travel crib, WiFi
Sleeps 18 • 8BR • Game Room • Gym • Theater

Vacation Home in Portage Park

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
$759 nightly
The price is $924
Jan 7 - Jan 8, 2026
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
Exterior detail
Master qtr close to nature & easy urban facilities

Vacation Home in Riverwoods

Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (73)
"It was a great respite."
United States
VIncent L.
$174 nightly
The price is $185
Dec 15 - Dec 16
Total with taxes and fees
Master qtr close to nature & easy urban facilities
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vacation Home in Worth

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
$299 nightly
The price is $319
Dec 11 - Dec 12
Total with taxes and fees
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Dining
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard

Vacation Home in Schaumburg

Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
$158 nightly
The price is $169
Dec 11 - Dec 12
Total with taxes and fees
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
Exterior
Coziest estate home 20 minutes to downtown

Vacation Home in Willow Springs

Coziest estate home 20 minutes to downtown
8.8 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!"
United States
Gabriela N.
$372 nightly
The price is $398
Dec 11 - Dec 12
Total with taxes and fees
Coziest estate home 20 minutes to downtown
Smart TV
Getaway Near ORD With Great Local Amenities

Vacation Home in Des Plaines

Getaway Near ORD With Great Local Amenities
9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
$263 nightly
The price is $278
Dec 11 - Dec 12
Total with taxes and fees
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop
Modern Apt in Trendy Neighborhood w/ Free Parking

Vacation Home in Avondale

Modern Apt in Trendy Neighborhood w/ Free Parking
2.0 star property
$159 nightly
The price is $185
Dec 14 - Dec 15
Total with taxes and fees
Modern Apt in Trendy Neighborhood w/ Free Parking
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very Good, (19)
"Very nice place "
United States
Elliot H.
$224 nightly
The price is $239
Dec 11 - Dec 12
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in La Grange Highlands

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
$251 nightly
The price is $268
Dec 11 - Dec 12
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Vacation Home in Wheaton

✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (55)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
$294 nightly
The price is $312
Dec 11 - Dec 12
Total with taxes and fees
✽ Charming Cottage ✽ close to College/Town/Station
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Vacation Home in Lisle

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
$269 nightly
The price is $286
Dec 15 - Dec 16
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Vacation Home in Wood Dale

Wonderful in Wood Dale, right by O’Hare airport!
10.0 out of 10, Exceptional, (17)
"Great property and great host!"
United States
Darin H.
$371 nightly
The price is $393
Dec 11 - Dec 12
Total with taxes and fees
Wonderful in Wood Dale, right by O’Hare airport!
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (13)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
$434 nightly
The price is $497
Dec 11 - Dec 12
Total with taxes and fees
Vintage Urban Retreat
Smart TV
Enamored in Elmhurst

Vacation Home in Elmhurst

Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
$465 nightly
The price is $493
Dec 11 - Dec 12
Total with taxes and fees
Enamored in Elmhurst
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Vacation Home in Skokie

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
10.0 out of 10, Exceptional, (34)
"Great place to congregate with family and a pet. Lots of room to gather."
United States
Leone W.
$656 nightly
The price is $702
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

Vacation Home in Elmhurst

LUXE 3 BR, 2 BA + Hot Tub
8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
$309 nightly
The price is $330
Dec 15 - Dec 16
Total with taxes and fees
LUXE 3 BR, 2 BA + Hot Tub
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Vacation Home in Oak Park

Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
$426 nightly
The price is $487
Dec 11 - Dec 12
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm
TV
Modern 4BR Retreat Near MDW | LCP Collection

Vacation Home in Burbank

Modern 4BR Retreat Near MDW | LCP Collection
9.4 out of 10, Exceptional, (6)
"Check in was easy and house was in safe neighborhood. It was a quick stay really a place to sleep for a few hours on our way through. "
United States
Stephanie S.
$429 nightly
The price is $459
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern 4BR Retreat Near MDW | LCP Collection
Private kitchen
Great Location! Beautiful Home Near Downtown Westmont

Vacation Home in Westmont

Great Location! Beautiful Home Near Downtown Westmont
9.8 out of 10, Exceptional, (11)
"Great property. Great host. Would stay again."
United States
Aliasger S.
$185 nightly
The price is $196
Dec 19 - Dec 20
Total with taxes and fees
Great Location! Beautiful Home Near Downtown Westmont
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.
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Top Northwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Everything was prefect. My only gripe was the heat was not heating as it should on 80 degrees. It was 20 degrees outside everyday. Other than that i will definitely return for another stay.. staff and Valetn were very professional and accommodating...10 star stay..."
Craig 4-night trip
Posted 5 hours ago
Embassy Suites by Hilton Chicago Downtown River North

Find out more about Northwest Side

Northwest Side Vacation Homes information

Number of reviews
389
Accommodation
336 Vacation Homes
Lowest Price
$185
Highest Price
$924

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