Holiday Homes in West Side

Start date: Check-in selected.
To Date
End date: Check-out

  • 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

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Featured Holiday Homes in West Side

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

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

2.0 star property
Whiting
10.0 out of 10, Exceptional, (11)
"Beautifully done and lovely owners! Super accommodating. Will definitely return. "
United States
Tim and Becky A.
The price is NZ$245
includes taxes & fees
18 Nov - 19 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Exterior
A quiet stay while you are away

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is NZ$339
includes taxes & fees
24 Nov - 25 Nov
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
9.6 out of 10, Exceptional, (53)
"The owner was amazing house was nice and clean everything was perfect we had a really great time!"
United States
Krystal N.
The price is NZ$583
includes taxes & fees
18 Nov - 19 Nov
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Interior
Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home

2.0 star property
Belmont Cragin
The price is NZ$893
includes taxes & fees
19 Nov - 20 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
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, (73)
"Easy check in / out, and a beautiful property. Thank you for having us!"
United States
Adam D.
The price is NZ$325
includes taxes & fees
19 Nov - 20 Nov
Master qtr close to nature & easy urban facilities
Interior
Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater

2.0 star property
Portage Park
The price is NZ$1,526
includes taxes & fees
18 Nov - 19 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
Fridge, microwave, oven, stovetop
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Hazel Crest
7.4 out of 10, Good, (10)
"Good quiet location "
United States
Augusto D.
The price is NZ$525
includes taxes & fees
18 Nov - 19 Nov
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Smart TV
Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."
United States
Dorde U.
The price is NZ$490
includes taxes & fees
19 Nov - 20 Nov
Getaway Near ORD With Great Local Amenities
Exterior
Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown

Willow Springs
8.8 out of 10, Excellent, (14)
"Short"
United States
Brian H.
The price is NZ$700
includes taxes & fees
18 Nov - 19 Nov
Coziest estate home 20 minutes to downtown
Microwave, oven, stovetop, dishwasher
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
7.8 out of 10, Good, (13)
"This space was perfect for our short stay in the city; plenty of parking space for our vehicles in a nice neighborhood, a quaint living room for socializing before and after our event and comfortable beds overnight. Although we didn’t take advantage, the downstairs bar would have been a cool space for a night cap. The host was very amenable, responsive and supportive. "
United States
Michael M.
The price is NZ$426
includes taxes & fees
18 Nov - 19 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

La Grange Highlands
10.0 out of 10, Exceptional, (2)
"Very quiet and private and cl9se to alot of things "
United States
Kenneth W.
The price is NZ$456
includes taxes & fees
18 Nov - 19 Nov
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Exterior detail
Vintage Urban Retreat

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is NZ$825
includes taxes & fees
18 Nov - 19 Nov
Vintage Urban Retreat
Smart TV
Enamored in Elmhurst

Enamored in Elmhurst

2.0 star property
Elmhurst
10.0 out of 10, Exceptional, (13)
"The house is lovely and located in a quiet, nice neighborhood. Our host Mark was very accommodating and responsive. When we informed him thatthe pack-and-play and high chair advertised in the listing were not there, he personally went out and bought new ones, and delivered them. We would certainly stay at this property again.he went out"
United States
Elena L.
The price is NZ$868
includes taxes & fees
18 Nov - 19 Nov
Enamored in Elmhurst
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is NZ$543
includes taxes & fees
18 Nov - 19 Nov
✽ Charming Cottage ✽ close to College/Town/Station
Terrace/patio
Modern Victorian Vibes ❤️ | Character & Charm

Modern Victorian Vibes ❤️ | Character & Charm

Oak Park
10.0 out of 10, Exceptional, (26)
"This was my first time booking here and it was amazing. The host was quick to communicate, and everything was smooth and easy to do. Definitely will book here again the next time my family is in town. "
United States
William K.
The price is NZ$979
includes taxes & fees
2 Dec - 3 Dec
Modern Victorian Vibes ❤️ | Character & Charm
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
9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
The price is NZ$512
includes taxes & fees
19 Nov - 20 Nov
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Fridge, microwave, oven, stovetop
Beautiful House in Carol Stream near Downtown Chicago

Beautiful House in Carol Stream near Downtown Chicago

Carol Stream
10.0 out of 10, Exceptional, (3)
"The property was nice. Perfect for our guys trip. "
United States
Jay S.
The price is NZ$943
includes taxes & fees
18 Nov - 19 Nov
Beautiful House in Carol Stream near Downtown Chicago
Smart TV, video games, table football, ping pong
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK

Your Chicago Hub~ 4 minute Walk to Train~ Pets OK

Brookfield
10.0 out of 10, Exceptional, (3)
"This house is a 5 star VRBO!The amenities are amazing! Coffee barsGames for kidsComfortable spacesNice kitchenGreat beddingOur host was very responsive and flexible. "
United States
Barbara R.
Your Chicago Hub~ 4 minute Walk to Train~ Pets OK
Fridge, microwave, oven, stovetop
Two Kings Chicago A unique royal environment, kingly comfort!

Two Kings Chicago A unique royal environment, kingly comfort!

Villa Park
10.0 out of 10, Exceptional, (1)
"Art & Milda were fantastic hosts! Very responsive to all inquiries and requests. The home was beautiful. Very comfy beds and recliners! So many perks you never knew you wanted. Will definitely stay again. Thank you Art & Milda!"
United States
Lisa V.
The price is NZ$679
includes taxes & fees
18 Nov - 19 Nov
Two Kings Chicago A unique royal environment, kingly comfort!
Interior
Sleeps 24+ Luxury house Near Chicago 12 king beds

Sleeps 24+ Luxury house Near Chicago 12 king beds

Des Plaines
10.0 out of 10, Exceptional, (2)
"We really enjoyed staying in this house. It was very clean and spacious. Excellent for larger groups!"
United States
TheBrittinghams
The price is NZ$11,697
includes taxes & fees
24 Nov - 25 Nov
Sleeps 24+ Luxury house Near Chicago 12 king beds
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

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

10/10 Excellent
"Very nice and clean option for anyone working in the area. Very nice host! Thank you for a simple and enjoyable stay! "
Colin 1-night trip
Posted 3 days ago
Hotel Chicago West Loop, SureStay Collection by Best Western

Find out more about West Side

West Side Holiday Homes information

Number of reviews
Accommodation
 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia