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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for West Side vacation 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, (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 ￥36,613
￥162,675 total
includes taxes & fees
Sep 17 - Sep 18
Sleeps 18 • 7BR • Gym • Game Room • Theater
Game room

2. Wabash 4BR - Pool, Free In & Out Parking 1

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is ￥76,805
￥108,237 total
includes taxes & fees
Oct 8 - Oct 9
Wabash 4BR - Pool, Free In & Out Parking 1
Living area

3. 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, 33, (33 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 ￥22,811
￥46,095 total
includes taxes & fees
Sep 15 - Sep 16
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Living area

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

4BR Retreat w/ Theater, Arcade, Gym and Firepit
Belmont Cragin
10.0 out of 10, 6, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ￥26,685
￥103,634 total
includes taxes & fees
Sep 22 - Sep 23
4BR Retreat w/ Theater, Arcade, Gym and Firepit
Private kitchen

5. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, 3, (3 reviews)
"Beautiful house. Lots of room and the games in the basement were awesome. Our grandsons loved them. The back yard is very nice too. The neighborhood is very nice. Everyone is so friendly. We had a great time."
United States
kim r.
The price is ￥23,515
￥86,663 total
includes taxes & fees
Sep 17 - Sep 18
Game Room • Fire-pit • Playground • Gym • Billiard
Living area

6. 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, 4, (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 ￥27,650
￥35,347 total
includes taxes & fees
Sep 22 - Sep 23
Attractive Coach House Apartment for rent in Oak Park.
Exterior

7. 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, 3, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥29,309
￥52,719 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Fitness facility

8. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is ￥282,489
￥615,571 total
includes taxes & fees
Sep 29 - Sep 30
Brand New 12 Bedroom Mansion
Private kitchen

9. 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, 2, (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 ￥29,493
￥73,127 total
includes taxes & fees
Sep 22 - Sep 23
Classic Forest Park Foursquare < 1 Mi to Blue Line
Room

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

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, 3, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is ￥15,484
￥110,913 total
includes taxes & fees
Sep 22 - Sep 23
Arcade • Theater • Gym • Office • Sleeps 15
Exterior detail

11. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, 33, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is ￥38,018
￥89,422 total
includes taxes & fees
Sep 21 - Sep 22
Oak Park Victorian by FLW Studio
Property grounds

12. 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, 34, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥24,424
￥34,409 total
includes taxes & fees
Sep 29 - Sep 30
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Dining

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, 8, (8 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 ￥40,868
￥166,158 total
includes taxes & fees
Sep 20 - Sep 21
Sleeps 18 • 8BR • Game Room • Gym • Theater
Dining

14. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, 58, (58 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is ￥27,650
￥57,023 total
includes taxes & fees
Sep 21 - Sep 22
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen

15. 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, 23, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is ￥29,677
￥68,394 total
includes taxes & fees
Sep 22 - Sep 23
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Beach

16. 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, 192, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is ￥61,444
￥144,621 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Interior

17. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, 23, (23 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is ￥25,653
￥50,450 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Home by O'Hare + EV Plug
Outdoor dining

18. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, 44, (44 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is ￥46,452
￥103,384 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
Room

19. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
The price is ￥37,634
￥53,242 total
includes taxes & fees
Sep 21 - Sep 22
Beautifully furnished one bedroom loft located in Chicago's South side suburb
Dining

20. Spacious 4BR near Northwestern with King Beds + Crib

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, 4, (4 reviews)
"The place was perfect for our family visiting for our daughter’s wedding. Close to every place we needed to go. The home was clean and everything we needed was provided for us."
United States
Cindy S.
The price is ￥35,253
￥79,735 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 4BR near Northwestern with King Beds + Crib
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

Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

10/10 Excellent
"Great location, lots of restaurants within walking distance, close proximity to public transportation. Parking rates were reasonable for the location. Definitely would stay there again."
John 3-night trip
Posted less than an hour ago
Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

West Side Vacation Homes information

Number of reviews
434
Accommodation
54 Vacation Homes
Lowest Price
￥34,409
Highest Price
￥166,158

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