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 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for West Side vacation homes

Lounge by the fire pit

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is ￥15,297
￥91,101 total
includes taxes & fees
Oct 6 - Oct 7
Theater • Game Room • Gym • Firepit • 4BR Home
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

2. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is ￥44,097
￥129,777 total
includes taxes & fees
Oct 5 - Oct 6
4 BR • Theater Room • Gym • Walk to Lincoln Park!
Room

3. 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 ￥16,434
￥114,562 total
includes taxes & fees
Sep 30 - Oct 1
Arcade • Theater • Gym • Office • Sleeps 15
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

4. 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, (34 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is ￥23,375
￥45,216 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A white two-story house with a porch, steps, and a small table with chairs.

5. 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 ￥27,531
￥80,355 total
includes taxes & fees
Sep 30 - Oct 1
Oak Park Victorian by FLW Studio
A single-story house with a covered porch, a front door, and a small garden area.

6. 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 ￥29,892
￥53,862 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

7. 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 ￥30,223
￥75,611 total
includes taxes & fees
Sep 30 - Oct 1
Classic Forest Park Foursquare < 1 Mi to Blue Line
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.4 out of 10, Exceptional, (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 ￥17,057
￥75,193 total
includes taxes & fees
Oct 1 - Oct 2
Game Room • Fire-pit • Playground • Gym • Billiard
A modern living room with a sectional sofa, a coffee table, and a TV.

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 ￥28,334
￥36,582 total
includes taxes & fees
Oct 6 - Oct 7
Attractive Coach House Apartment for rent in Oak Park.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

10. 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 ￥23,961
￥137,523 total
includes taxes & fees
Oct 5 - Oct 6
Sleeps 18 • 8BR • Game Room • Gym • Theater
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

11. 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, (44 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is ￥57,927
￥109,166 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

12. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (63 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,334
￥54,730 total
includes taxes & fees
Sep 30 - Oct 1
LUXE 3 BR, 2 BA + Hot Tub
A dining area with a wooden table set for four, chairs, a vase with yellow flowers, and a kitchen in the background.

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

Spacious 4BR near Northwestern with King Beds + Crib
Evanston
10.0 out of 10, Exceptional, (5 reviews)
"Spacious home that accommodates all our guests. Very close to Northwestern University so travel was easy! Home was clean and well taken care of. Would definitely recommend to others and would stay agin when I’m in the area."
United States
Melissa C.
The price is ￥26,681
￥70,559 total
includes taxes & fees
Sep 30 - Oct 1
Spacious 4BR near Northwestern with King Beds + Crib
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

14. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥17,189
￥44,075 total
includes taxes & fees
Sep 30 - Oct 1
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

15. 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, (193 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is ￥56,668
￥131,302 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A modern kitchen with wooden cabinets, stainless steel appliances, and a white tiled backsplash.

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

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Property is new and really nice. Super clean and well put together. Would stay here again."
United States
Devin D.
Wabash 4BR - Pool, Free In & Out Parking 1
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

17. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (24 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 ￥26,917
￥52,372 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Home by O'Hare + EV Plug
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

18. 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 ￥47,601
￥103,223 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

19. 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 ￥19,991
￥34,366 total
includes taxes & fees
Sep 30 - Oct 1
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A wooden deck with a railing, a staircase, and a window with a wreath.

20. 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, Exceptional, (35 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,525
￥32,281 total
includes taxes & fees
Oct 4 - Oct 5
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
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

Hyatt Place Chicago Medical/University District

Hyatt Place Chicago Medical/University District

10/10 Excellent
"Lovely hotel, the employees were kind and polite. House keeping did an amazing job. I love that there is a Starbucks on the main floor. Highly recommend and my room was spacious!"
Marlette 1-night trip
Posted 1 hour ago
Hyatt Place Chicago Medical/University District

Find out more about West Side

West Side Vacation Homes information

Number of reviews
401
Accommodation
54 Vacation Homes
Lowest Price
￥32,281
Highest Price
￥137,523

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