Holiday 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
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for West Side holiday 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 NZ$1,367
includes taxes & fees
2 Mar - 3 Mar
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)
"Everything was very comfortable and Jay did a great job of showing the house. I would definitely come back again"
United States
Fred D.
The price is NZ$370
includes taxes & fees
2 Mar - 3 Mar
A quiet stay while you are away
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, (57 reviews)
"Very clean and comfortable! Great place for our short stay! So much space it was great!"
United States
David L.
The price is NZ$537
includes taxes & fees
4 Mar - 5 Mar
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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 NZ$334
includes taxes & fees
9 Mar - 10 Mar
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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 NZ$323
includes taxes & fees
5 Mar - 6 Mar
Master qtr close to nature & easy urban facilities
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 NZ$497
includes taxes & fees
3 Mar - 4 Mar
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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 NZ$509
includes taxes & fees
2 Mar - 3 Mar
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
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 NZ$767
includes taxes & fees
2 Mar - 3 Mar
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 NZ$510
includes taxes & fees
12 Mar - 13 Mar
✽ Charming Cottage ✽ close to College/Town/Station
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 NZ$947
includes taxes & fees
2 Mar - 3 Mar
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
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 NZ$753
includes taxes & fees
1 Mar - 2 Mar
Modern 4BR Retreat Near MDW | LCP Collection
Interior

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is NZ$855
includes taxes & fees
3 Mar - 4 Mar
Near Lake and Museum • Modern • Game Area
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 NZ$555
includes taxes & fees
1 Mar - 2 Mar
Luxury Suite in Glen Ellyn, IL USA
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 NZ$815
includes taxes & fees
3 Mar - 4 Mar
Oak Park Victorian by FLW Studio
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 NZ$795
includes taxes & fees
1 Mar - 2 Mar
4BR Near Woodfield Mall & Metra | LCP Collection
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 NZ$606
includes taxes & fees
3 Mar - 4 Mar
LUXE 3 BR, 2 BA + Hot Tub
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 NZ$860
includes taxes & fees
1 Mar - 2 Mar
Enamored in Elmhurst
Private kitchen

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.6 out of 10, Exceptional, (63 reviews)
"We enjoyed our stay"
United States
Lukose K.
The price is NZ$472
includes taxes & fees
1 Mar - 2 Mar
Your Next Vacation Home
Outdoor dining

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (23 reviews)
"Had a nice time. Great location!"
United States
Jinjer M.
The price is NZ$428
includes taxes & fees
1 Mar - 2 Mar
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent
"Very clean, good breakfast options, close to United Center. "
Ashley 1-night trip
Posted 1 day ago
Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

West Side Holiday Homes information

Number of reviews
498
Accommodation
68 Holiday Homes
Lowest Price
NZ$323
Highest Price
NZ$1,367

Explore a world of travel with Expedia