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

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Our top choices for West Side vacation homes

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 ¥24,709
¥148,821 total
includes taxes & fees
Sep 30 - Oct 1
Sleeps 18 • 7BR • Gym • Game Room • Theater

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ¥13,896
¥88,379 total
includes taxes & fees
Sep 24 - Sep 25
Theater • Game Room • Gym • Firepit • 4BR Home

3. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is ¥20,787
¥45,171 total
includes taxes & fees
Oct 12 - Oct 13
A quiet stay while you are away

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (9 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 ¥41,852
¥170,467 total
includes taxes & fees
Oct 22 - Oct 23
Sleeps 18 • 8BR • Game Room • Gym • Theater

5. Complete 1BR Fully Furnished Home

Complete 1BR Fully Furnished Home
Downtown Chicago
The price is ¥22,495
¥52,603 total
includes taxes & fees
Sep 29 - Sep 30
Complete 1BR Fully Furnished Home

6. 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, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is ¥23,297
¥45,568 total
includes taxes & fees
Sep 23 - Sep 24
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

7. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is ¥18,186
¥116,947 total
includes taxes & fees
Sep 30 - Oct 1
Arcade • Theater • Gym • Office • Sleeps 15

8. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is ¥36,082
¥89,260 total
includes taxes & fees
Sep 29 - Sep 30
Oak Park Victorian by FLW Studio

9. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 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 ¥28,238
¥35,381 total
includes taxes & fees
Sep 23 - Sep 24
Attractive Coach House Apartment for rent in Oak Park.

10. 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, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ¥29,792
¥53,682 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

11. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is ¥30,121
¥75,356 total
includes taxes & fees
Sep 27 - Sep 28
Classic Forest Park Foursquare < 1 Mi to Blue Line

12. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (43 reviews)
"We had a really nice stay at the Village Inn. We appreciated that artistic furnishings and decorations, and the thoughtful touches throughout. (We are a white noise family, so we were very happy to find a white noise machine in every bedroom!)The neighborhood is very quiet and also close to great shops and restaurants as well as the train. We enjoyed being able to walk to dinner in the evening, and walk to the train to take a short ride right to the Art Institute. The kitchen was great for...
United States
Andrea M.
The price is ¥45,652
¥95,438 total
includes taxes & fees
Sep 29 - Sep 30
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

13. 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
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is ¥42,664
¥87,097 total
includes taxes & fees
Sep 28 - Sep 29
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

14. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is ¥18,496
¥32,405 total
includes taxes & fees
Oct 4 - Oct 5
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

15. Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
9.8 out of 10, Exceptional, (6 reviews)
The price is ¥26,983
¥76,664 total
includes taxes & fees
Sep 23 - Sep 24
Modern 3BR Apartment Near North Ave Shops

16. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (61 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is ¥28,238
¥57,733 total
includes taxes & fees
Sep 23 - Sep 24
LUXE 3 BR, 2 BA + Hot Tub

17. Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Lincoln Park
9.8 out of 10, Exceptional, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is ¥62,924
¥147,912 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

18. Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home

Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is ¥75,593
¥161,030 total
includes taxes & fees
Sep 27 - Sep 28
Sleeps 10 + Coffee bar + Game Room + Train to CHGO - Holiday Home

19. AeroStay Retreat – 4BR Home Near O’Hare Airport!

AeroStay Retreat – 4BR Home Near O’Hare Airport!
Wood Dale
9.4 out of 10, Exceptional, (3 reviews)
"Large space great for family"
United States
Remona S.
The price is ¥42,358
¥88,120 total
includes taxes & fees
Sep 28 - Sep 29
AeroStay Retreat – 4BR Home Near O’Hare Airport!

20. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (44 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is ¥47,441
¥109,459 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
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

Find out more about West Side

West Side Vacation Homes information

Number of reviews
373
Accommodation
54 Vacation Homes
Lowest Price
¥32,405
Highest Price
¥170,467

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