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

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for West Side holiday homes

Terrace/patio

1. 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 £702
includes taxes & fees
12 Aug - 13 Aug
Sleeps 18 • 7BR • Gym • Game Room • Theater
Exterior

2. Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
10.0 out of 10, Exceptional, (2 reviews)
"From booking to leaving, the experience here was amazing and easy to navigate. Great building and I have never had a more communicative host situation. Would gladly book again."
United States
Erin G.
The price is £810
includes taxes & fees
22 Aug - 23 Aug
Envitae Hotel, 4BR Modern Sleek Apartment
3 bedrooms, iron/ironing board, travel cot, WiFi

3. 3BR · Steps from McCormick · Balcony & Gym

3BR · Steps from McCormick · Balcony & Gym
Near South Side
9.8 out of 10, Exceptional, (6 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
3BR · Steps from McCormick · Balcony & Gym
TV

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

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, Exceptional, (3 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is £497
includes taxes & fees
11 Aug - 12 Aug
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Smart TV

5. 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 £227
includes taxes & fees
10 Aug - 11 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Exterior detail

6. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (32 reviews)
"Would stay there again"
United States
Margaret L.
The price is £447
includes taxes & fees
12 Aug - 13 Aug
Oak Park Victorian by FLW Studio
Interior

7. 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 £460
includes taxes & fees
12 Aug - 13 Aug
Vintage Urban Retreat
5 bedrooms, iron/ironing board, travel cot, WiFi

8. Theater Room and Gym | 4BR Near Lincoln Park

Theater Room and Gym | 4BR Near Lincoln Park
Lincoln Park
The price is £581
includes taxes & fees
11 Aug - 12 Aug
Theater Room and Gym | 4BR Near Lincoln Park
Exterior

9. 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 £249
includes taxes & fees
1 Sept - 2 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Interior

10. 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 £515
includes taxes & fees
9 Aug - 10 Aug
Chic 3bed 2bath Home with free parking close to United Center
TV

11. 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 £436
includes taxes & fees
11 Aug - 12 Aug
Spacious 5BR 2BA Berwyn Home
Living area

12. 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 £173
includes taxes & fees
11 Aug - 12 Aug
Attractive Coach House Apartment for rent in Oak Park.
7 bedrooms, desk, iron/ironing board, travel cot

13. 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 £566
includes taxes & fees
11 Aug - 12 Aug
Arcade • Theater • Gym • Office • Sleeps 15
Coffee/tea maker, fridge, microwave, oven

14. 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 £366
includes taxes & fees
11 Aug - 12 Aug
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Dining

15. Spacious 5-bed 2-bath house - Berwyn

Spacious 5-bed 2-bath house - Berwyn
Berwyn
The price is £427
includes taxes & fees
11 Aug - 12 Aug
Spacious 5-bed 2-bath house - Berwyn
Dining

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (5 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is £856
includes taxes & fees
19 Aug - 20 Aug
Sleeps 18 • 8BR • Game Room • Gym • Theater
Exterior

17. ✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (70 reviews)
"This was the perfect place for our short stay!"
United States
Laurie R.
The price is £241
includes taxes & fees
18 Aug - 19 Aug
✽ Charming Cottage ✽ close to College/Town/Station
Dining

18. 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 £272
includes taxes & fees
16 Aug - 17 Aug
LUXE 3 BR, 2 BA + Hot Tub
Coffee/tea maker, fridge, microwave, oven

19. 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 £467
includes taxes & fees
18 Aug - 19 Aug
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Coffee/tea maker, fridge, microwave, oven

20. *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 £308
includes taxes & fees
9 Aug - 10 Aug
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
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

Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

10/10 Excellent
"Amazing stay, clean room, friendly staff, beautiful rooftop pool."
Brianna 2-night trip
Posted 3 hours ago
Holiday Inn & Suites Chicago - Downtown by IHG

Find out more about West Side

West Side Holiday Homes information

Number of reviews
326
Accommodation
61 Holiday Homes
Lowest Price
£173
Highest Price
£856

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