A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

Holiday Homes in West Side

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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$2,446
includes taxes & fees
9 Aug - 10 Aug
Sleeps 18 • 7BR • Gym • Game Room • Theater
Property grounds

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (19 reviews)
"The property was clean and the location was great."
United States
Steven C.
The price is NZ$1,815
includes taxes & fees
30 July - 31 July
ENVITAE Hotel, 4BR Luxury Modern Apartments
Interior

Chic 3bed 2bath Home with free parking close to United Center

Chic 3bed 2bath Home with free parking close to United Center
Oak Park
9.8 out of 10, Exceptional, (19 reviews)
"Overall just great lovely area and chill place, rooms was great and I love the Roku tvs to sit back In chill!"
United States
Chantrice A.
The price is NZ$1,172
includes taxes & fees
28 July - 29 July
Chic 3bed 2bath Home with free parking close to United Center
Interior

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (15 reviews)
"It was a very nice neighborhood, with many restaurants and retail establishments in proximity. We really enjoyed our stay and our host was an excellent when it comes to communication."
United States
Tim P.
The price is NZ$1,285
includes taxes & fees
10 Aug - 11 Aug
Vintage Urban Retreat
Exterior detail

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
The price is NZ$1,294
includes taxes & fees
28 July - 29 July
Oak Park Victorian by FLW Studio
Coffee/tea maker, fridge, microwave, oven

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
9.6 out of 10, Exceptional, (21 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is NZ$1,080
includes taxes & fees
28 July - 29 July
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Exterior

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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is NZ$603
includes taxes & fees
24 Aug - 25 Aug
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Living area

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
7.0 out of 10, Good, (2 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is NZ$403
includes taxes & fees
28 July - 29 July
Attractive Coach House Apartment for rent in Oak Park.
TV

Spacious 5BR 2BA Berwyn Home

Spacious 5BR 2BA Berwyn Home
Berwyn
10.0 out of 10, Exceptional, (1 review)
"experience was good i loved it honestly "
United States
jamya w.
The price is NZ$978
includes taxes & fees
12 Aug - 13 Aug
Spacious 5BR 2BA Berwyn Home
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, (30 reviews)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is NZ$514
includes taxes & fees
3 Aug - 4 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Smart TV, offices

South Loop · 3 Kings · Steps from McCormick Place

South Loop · 3 Kings · Steps from McCormick Place
Near South Side
9.6 out of 10, Exceptional, (4 reviews)
"Great space!"
United States
Kyle H.
The price is NZ$967
includes taxes & fees
16 Aug - 17 Aug
South Loop · 3 Kings · Steps from McCormick Place
TV

4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (2 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$2,118
includes taxes & fees
3 Aug - 4 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Dining

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (53 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is NZ$685
includes taxes & fees
13 Aug - 14 Aug
LUXE 3 BR, 2 BA + Hot Tub
Microwave, oven, stovetop, dishwasher

Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town

Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town
Bensenville
10.0 out of 10, Exceptional, (3 reviews)
"Great property, and very responsive host!"
United States
Bridget M.
The price is NZ$2,192
includes taxes & fees
19 Aug - 20 Aug
Grand 5BR, 4.5BA Game Rm, Near O’Hare, & Down Town
Coffee/tea maker, fridge, microwave, oven

Charming Retreat in Evanston Right Next to Beach

Charming Retreat in Evanston Right Next to Beach
South Evanston
8.2 out of 10, Very good, (10 reviews)
"It was really easy to access stores and restaurants. It was also very clean and nice."
United States
matthew z.
The price is NZ$827
includes taxes & fees
28 July - 29 July
Charming Retreat in Evanston Right Next to Beach
Dining

Spacious 5-bed 2-bath house - Berwyn

Spacious 5-bed 2-bath house - Berwyn
Berwyn
The price is NZ$978
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bed 2-bath house - Berwyn
Coffee/tea maker, fridge, microwave, oven

*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, (63 reviews)
"Checking in was easy, the place is as advertised, communication was easy as well, had no problems, will be staying there again. "
United States
Joe M.
The price is NZ$717
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Coffee/tea maker, fridge, microwave, oven

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (2 reviews)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is NZ$1,085
includes taxes & fees
28 July - 29 July
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Coffee/tea maker, fridge, microwave, oven

Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, comfortable home in a good location. This was a great place to stay while visiting Chicago. "
United States
Pelayo M.
The price is NZ$992
includes taxes & fees
28 July - 29 July
Wonderful in Wood Dale, right by O’Hare airport!
7 bedrooms, desk, iron/ironing board, travel cot

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is NZ$1,404
includes taxes & fees
10 Aug - 11 Aug
Arcade • Theater • Gym • Office • Sleeps 15
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

Chicago Parthenon Hostel

Chicago Parthenon Hostel

10/10 Excellent
"Everything was nice. Close to a lot of attractions. I just wish there was a small fridge in the room."
Emma 1-night trip
Posted 6 hours ago
Chicago Parthenon Hostel

Find out more about West Side

West Side Holiday Homes information

Number of reviews
298
Accommodation
61 Holiday Homes
Lowest Price
NZ$403
Highest Price
NZ$2,446

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