Holiday Homes in West Side

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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for West Side holiday homes

Terrace/patio
Sleeps 18 • 7BR • Gym • Game Room • Theater

Holiday Home in Austin

Sleeps 18 • 7BR • Gym • Game Room • Theater
2.0 star property
Sleeps 18 • 7BR • Gym • Game Room • Theater
Exterior detail
Master qtr close to nature & easy urban facilities

Holiday Home in Riverwoods

Master qtr close to nature & easy urban facilities
9.8 out of 10, Exceptional, (73)
"Amazing area, loved the feel of it all and very quiet neighborhood."
United States
Joshua K.
The price is €163
includes taxes & fees
25 Dec - 26 Dec
Master qtr close to nature & easy urban facilities
Property grounds
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Holiday Home in Robertsdale

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
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.
The price is €174
includes taxes & fees
17 Dec - 18 Dec
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

Holiday 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.
The price is €281
includes taxes & fees
16 Dec - 17 Dec
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Dining
Getaway Near ORD With Great Local Amenities

Holiday 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.
The price is €245
includes taxes & fees
16 Dec - 17 Dec
Getaway Near ORD With Great Local Amenities
Smart TV
Modern Apt in Trendy Neighborhood w/ Free Parking

Holiday Home in Avondale

Modern Apt in Trendy Neighborhood w/ Free Parking
2.0 star property
The price is €177
includes taxes & fees
28 Dec - 29 Dec
Modern Apt in Trendy Neighborhood w/ Free Parking
Fridge, microwave, oven, stovetop
Coziest estate home 20 minutes to downtown

Holiday 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.
The price is €351
includes taxes & fees
16 Dec - 17 Dec
Coziest estate home 20 minutes to downtown
2 bedrooms, iron/ironing board, WiFi, bed sheets
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Holiday 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.
The price is €223
includes taxes & fees
16 Dec - 17 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Interior
Vintage Urban Retreat

Holiday Home in Oak Park

Vintage Urban Retreat
10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is €439
includes taxes & fees
17 Dec - 18 Dec
Vintage Urban Retreat
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Holiday 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
The price is €272
includes taxes & fees
16 Dec - 17 Dec
✽ Charming Cottage ✽ close to College/Town/Station
Dining
Theater • Game Room • Gym • Firepit • 4BR Home

Holiday Home in Belmont Cragin

Theater • Game Room • Gym • Firepit • 4BR Home
2.0 star property
The price is €446
includes taxes & fees
14 Jan - 15 Jan 2026
Theater • Game Room • Gym • Firepit • 4BR Home
Smart TV
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Maywood

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
8.0 out of 10, Very good, (20)
"Very nice place "
United States
Elliot H.
The price is €212
includes taxes & fees
17 Dec - 18 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Dining
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard

Holiday Home in Schaumburg

Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
Perfect modern 3-bedroom house Near Chicago • Fireplace & Yard
Fridge, microwave, oven, stovetop
Wonderful in Wood Dale, right by O’Hare airport!

Holiday 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.
The price is €343
includes taxes & fees
16 Dec - 17 Dec
Wonderful in Wood Dale, right by O’Hare airport!
Smart TV
Enamored in Elmhurst

Holiday Home in Elmhurst

Enamored in Elmhurst
2.0 star property
10.0 out of 10, Exceptional, (13)
"Great stay"
United States
Aaron B.
The price is €431
includes taxes & fees
16 Dec - 17 Dec
Enamored in Elmhurst
Dining
LUXE 3 BR, 2 BA + Hot Tub

Holiday 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.
The price is €288
includes taxes & fees
16 Dec - 17 Dec
LUXE 3 BR, 2 BA + Hot Tub
Outdoor dining
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Holiday Home in Lisle

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
9.6 out of 10, Exceptional, (19)
"The hosts were fantastic—very friendly and accommodating. The property itself was excellent, tucked away from the main road yet within walking distance of several restaurants, shops, and a supermarket. I would wholeheartedly recommend staying here if you're planning a trip to the Chicagoland area!"
United States
christian m.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
TV
Modern 4BR Retreat Near MDW | LCP Collection

Holiday 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.
Modern 4BR Retreat Near MDW | LCP Collection
Exterior detail
Modern Victorian Vibes ❤️ | Character & Charm

Holiday Home in Oak Park

Modern Victorian Vibes ❤️ | Character & Charm
10.0 out of 10, Exceptional, (27)
"Great location and walkable to restaurants. "
United States
Laura B.
Modern Victorian Vibes ❤️ | Character & Charm
Fridge, microwave, stovetop, dishwasher
Classic Forest Park Foursquare < 1 Mi to Blue Line

Holiday Home in Forest Park

Classic Forest Park Foursquare < 1 Mi to Blue Line
2.0 star property
The price is €356
includes taxes & fees
17 Dec - 18 Dec
Classic Forest Park Foursquare < 1 Mi to Blue Line
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

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Location it's the best from this hotel close to the Fulton Market. David in the restaurant area it's very friendly and makes you feel at home. Hotel staff in general are very nice. "
ANDRES 3-night trip
Posted 17 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

West Side Holiday Homes information

Number of reviews
362
Accommodation
68 Holiday Homes
Lowest Price
€163
Highest Price
€446

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