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

A dining area with a table set for a party, colorful drapes, and a sign that reads "Jessie's Bach Party".

1. Aloha 2.0 Tropical Oasis in Wicker Park Sleeps 23 with Backyard Patio

Aloha 2.0 Tropical Oasis in Wicker Park Sleeps 23 with Backyard Patio
West Town
9.8 out of 10, Exceptional, (15 reviews)
"We booked this apartment and their other one for a bachelorette. It was such an amazing time and everything Was so thoughtful . Perfect location too!"
United States
Lita T.
The price is ￥142,065
￥270,083 total
includes taxes & fees
Oct 30 - Oct 31
Aloha 2.0 Tropical Oasis in Wicker Park Sleeps 23 with Backyard Patio
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

2. 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 ￥10,996
￥84,717 total
includes taxes & fees
Oct 5 - Oct 6
Theater • Game Room • Gym • Firepit • 4BR Home
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

3. 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 ￥29,186
￥96,233 total
includes taxes & fees
Oct 7 - Oct 8
Game Room • Fire-pit • Playground • Gym • Billiard
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

4. 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 ￥20,205
￥34,462 total
includes taxes & fees
Oct 26 - Oct 27
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

5. 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 ￥33,938
￥159,893 total
includes taxes & fees
Oct 5 - Oct 6
Sleeps 18 • 8BR • Game Room • Gym • Theater
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,441
￥46,523 total
includes taxes & fees
Oct 12 - Oct 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A single-story house with a covered porch, a front door, and a small garden area.

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, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ￥29,976
￥54,013 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Room

8. 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 ￥28,153
￥129,729 total
includes taxes & fees
Oct 7 - Oct 8
Arcade • Theater • Gym • Office • Sleeps 15
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥20,718
￥47,886 total
includes taxes & fees
Nov 2 - Nov 3
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Communal lounging

10. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.0 out of 10, Wonderful, (4 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is ￥28,571
￥68,760 total
includes taxes & fees
Oct 15 - Oct 16
Cozy Studio Suite, Steps from River North & Shops
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

11. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
The price is ￥47,734
￥110,135 total
includes taxes & fees
Oct 8 - Oct 9
Chicago Riverhouse with private fenced in oasis
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 ￥28,413
￥58,090 total
includes taxes & fees
Oct 5 - Oct 6
LUXE 3 BR, 2 BA + Hot Tub
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

13. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (87 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥18,326
￥34,479 total
includes taxes & fees
Oct 8 - Oct 9
Master qtr close to nature & easy urban facilities
A modern living room with a sectional sofa, a coffee table, and a TV.

14. 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 ￥28,413
￥36,684 total
includes taxes & fees
Oct 5 - Oct 6
Attractive Coach House Apartment for rent in Oak Park.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

15. 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 ￥30,307
￥74,977 total
includes taxes & fees
Oct 14 - Oct 15
Classic Forest Park Foursquare < 1 Mi to Blue Line
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

16. 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 ￥49,091
￥103,429 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A wooden deck with a railing, a staircase, and a window with a wreath.

17. 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 ￥22,588
￥32,548 total
includes taxes & fees
Oct 5 - Oct 6
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

18. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (31 reviews)
"Super clean great location short drive to everything we wanted to see!"
United States
eric p.
The price is ￥32,991
￥84,538 total
includes taxes & fees
Oct 14 - Oct 15
ENVITAE Hotel, 4BR Luxury Modern Apartments
A white two-story house with a porch, steps, and a small table with chairs.

19. 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 ￥30,212
￥83,920 total
includes taxes & fees
Oct 5 - Oct 6
Oak Park Victorian by FLW Studio
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

20. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is ￥23,483
￥111,009 total
includes taxes & fees
Nov 4 - Nov 5
4 BR • Theater Room • Gym • Walk to Lincoln Park!
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 House Chicago Medical/University District

Hyatt House Chicago Medical/University District

10/10 Excellent
"Great place, great people, great food! Will definitely stay there again if in the area."
Helen 1-night trip
Posted 6 hours ago
Hyatt House Chicago Medical/University District

Find out more about West Side

West Side Vacation Homes information

Number of reviews
229
Accommodation
54 Vacation Homes
Lowest Price
￥32,548
Highest Price
￥270,083

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