Search Vacation Homes in West Side

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In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for West Side vacation homes

Property grounds
Sleeps 18 • 7BR • Gym • Game Room • Theater

Vacation Home in Austin

2.0 star property
$824 nightly
The price is $1,019
Jan 5 - Jan 6, 2026
Total with taxes and fees
Sleeps 18 • 7BR • Gym • Game Room • Theater
Fridge, microwave, oven, stovetop
Modern Apt in Trendy Neighborhood w/ Free Parking

Vacation Home in Avondale

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
Exterior detail
Master qtr close to nature & easy urban facilities

Vacation Home in Riverwoods

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
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Vacation Home in Robertsdale

2.0 star property
9.8 out of 10, Exceptional, (15)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
United States
Karen D.
$178 nightly
The price is $199
Dec 11 - Dec 12
Total with taxes and fees
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vacation Home in Worth

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
Smart TV
Getaway Near ORD With Great Local Amenities

Vacation Home in Des Plaines

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
Exterior
Coziest estate home 20 minutes to downtown

Vacation Home in Willow Springs

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
Exterior detail
Vintage Urban Retreat

Vacation Home in Oak Park

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.
$446 nightly
The price is $511
Dec 11 - Dec 12
Total with taxes and fees
Vintage Urban Retreat
4 bedrooms, iron/ironing board, travel crib, WiFi
Theater • Game Room • Gym • Firepit • 4BR Home

Vacation Home in Belmont Cragin

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
Private kitchen
Cozy Home in Suburbs near Chicago - pet friendly

Vacation Home in Bridgeview

2.0 star property
$301 nightly
The price is $322
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Home in Suburbs near Chicago - pet friendly
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Vacation Home in La Grange Highlands

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.
$257 nightly
The price is $275
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

10.0 out of 10, Exceptional, (54)
"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

9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
$267 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Vacation Home in Oak Park

10.0 out of 10, Exceptional, (26)
"Great location and walkable to restaurants. "
United States
Laura B.
$458 nightly
The price is $524
Dec 11 - Dec 12
Total with taxes and fees
Modern Victorian Vibes ❤️ | Character & Charm
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Vacation Home in Maywood

8.0 out of 10, Very Good, (19)
"Very nice place "
United States
Elliot H.
$227 nightly
The price is $242
Dec 11 - Dec 12
Total with taxes and fees
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop
Modern Stylish Comfort Near Casino and Hwy

Vacation Home in Homewood

2.0 star property
$389 nightly
The price is $416
Dec 15 - Dec 16
Total with taxes and fees
Modern Stylish Comfort Near Casino and Hwy
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

Vacation Home in Elmhurst

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
Smart TV
Enamored in Elmhurst

Vacation Home 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

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
TV
Modern 4BR Retreat Near MDW | LCP Collection

Vacation Home in Burbank

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.
$428 nightly
The price is $458
Jan 8 - Jan 9, 2026
Total with taxes and fees
Modern 4BR Retreat Near MDW | LCP Collection
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 West Side Hotel Reviews

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent
"Yes"
Gabriel 2-night trip
Posted 20 hours ago
Holiday Inn & Suites Chicago - Downtown by IHG

Find out more about West Side

West Side Vacation Homes information

Number of reviews
377
Accommodation
68 Vacation Homes
Lowest Price
$185
Highest Price
$1,019

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