Search Vacation Homes in West Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Mar 6 - Mar 8
In two months
Apr 17 - Apr 19
In three months
May 15 - May 17
In four months
Jun 12 - Jun 14

Our top choices for West Side vacation homes

Terrace/patio

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

Sleeps 18 • 7BR • Gym • Game Room • Theater
Austin
6.0 out of 10, (1 review)
"Ok place to fit large families if no other option available. Not suitable for kids with allergies as there are some opportunities in the cleanness and maintenance of the property.The communication were ok for reserving but very limited during the stay.The floor os severely damaged as well."
United States
Adrian Cesar C.
The price is ￥21,570
￥140,086 total
includes taxes & fees
Mar 3 - Mar 4
Sleeps 18 • 7BR • Gym • Game Room • Theater
Exterior

A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (34 reviews)
"great stay"
United States
matt R.
The price is ￥10,329
￥31,304 total
includes taxes & fees
Feb 24 - Feb 25
A quiet stay while you are away
Exterior detail

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (77 reviews)
"Nice , private and peaceful definitely will be back "
United States
BRANDEN J.
The price is ￥15,223
￥30,113 total
includes taxes & fees
Feb 24 - Feb 25
Master qtr close to nature & easy urban facilities
Property grounds

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (20 reviews)
"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 ￥18,016
￥26,262 total
includes taxes & fees
Feb 22 - Feb 23
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Smart TV

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very Good, (21 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is ￥22,968
￥46,413 total
includes taxes & fees
Feb 23 - Feb 24
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Fridge, microwave, oven, stovetop

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.4 out of 10, Exceptional, (56 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is ￥24,747
￥50,739 total
includes taxes & fees
Mar 19 - Mar 20
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
TV

Modern 4BR Retreat Near MDW | LCP Collection

Modern 4BR Retreat Near MDW | LCP Collection
Burbank
8.6 out of 10, Excellent, (7 reviews)
"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.
The price is ￥28,459
￥71,327 total
includes taxes & fees
Feb 22 - Feb 23
Modern 4BR Retreat Near MDW | LCP Collection
Fridge, microwave, oven, stovetop

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great place Great location "
United States
Josh W.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Dining

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (1 review)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥23,463
￥45,337 total
includes taxes & fees
Mar 2 - Mar 3
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Fridge, microwave, oven, stovetop

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very Good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is ￥25,450
￥76,001 total
includes taxes & fees
Feb 23 - Feb 24
4BR Near Woodfield Mall & Metra | LCP Collection
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14 reviews)
"Great location in a quiet neighborhood! Beautiful Victorian house that was perfect for our company. Every amenities you could ask for and washer/dryer was excellent for our international co founders and they were very impressed with dry time. We will be staying here every time we are in Chicago. "
United States
Mike B.
The price is ￥23,044
￥70,973 total
includes taxes & fees
Feb 23 - Feb 24
Vintage Urban Retreat
Outdoor dining

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (58 reviews)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is ￥26,294
￥46,226 total
includes taxes & fees
Mar 17 - Mar 18
✽ Charming Cottage ✽ close to College/Town/Station
Interior

Luxury Suite in Glen Ellyn, IL USA

Luxury Suite in Glen Ellyn, IL USA
Glen Ellyn
9.6 out of 10, Exceptional, (10 reviews)
"Was very comfortable. Had everything we needed except wash clothes. Walmart really close. "
United States
Debra B.
The price is ￥24,593
￥52,618 total
includes taxes & fees
Feb 21 - Feb 22
Luxury Suite in Glen Ellyn, IL USA
Smart TV, fireplace, books, video library

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Skokie
10.0 out of 10, Exceptional, (34 reviews)
"Beautiful property, great location, quiet, with plenty of curb parking directly in front. "
United States
carlos l.
The price is ￥34,940
￥88,839 total
includes taxes & fees
Feb 23 - Feb 24
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Smart TV

Enamored in Elmhurst

Enamored in Elmhurst
Elmhurst
10.0 out of 10, Exceptional, (16 reviews)
"Clean rooms, very helpful and friendly host, the house had everything we needed"
United States
Kaitlyn M.
The price is ￥36,622
￥80,913 total
includes taxes & fees
Feb 22 - Feb 23
Enamored in Elmhurst
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (29 reviews)
"Great location and walkable to restaurants. "
United States
Laura B.
The price is ￥22,968
￥73,573 total
includes taxes & fees
Feb 23 - Feb 24
Oak Park Victorian by FLW Studio
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (39 reviews)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is ￥22,346
￥50,468 total
includes taxes & fees
Feb 22 - Feb 23
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.6 out of 10, Exceptional, (62 reviews)
"We enjoyed our stay"
United States
Lukose K.
The price is ￥22,346
￥45,652 total
includes taxes & fees
Feb 22 - Feb 23
Your Next Vacation Home
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ￥11,600
￥80,144 total
includes taxes & fees
Feb 22 - Feb 23
Near Lake and Museum • Modern • Game Area
TV, foosball

New! 10-min to Downtown

New! 10-min to Downtown
Oak Park
The price is ￥38,795
￥93,848 total
includes taxes & fees
Feb 23 - Feb 24
New! 10-min to Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Side Hotel Reviews

The Hoxton Chicago

The Hoxton Chicago

10/10 Excellent
"Energy, decor, kindness/accommodations and perks. Love this hotel! "
Marla 1-night trip
Posted 2 days ago
The Hoxton Chicago

Find out more about West Side

West Side Vacation Homes information

Number of reviews
495
Accommodation
68 Vacation Homes
Lowest Price
￥26,262
Highest Price
￥140,086

Explore a world of travel with Expedia