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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for West Side vacation homes

1. 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 ￥12,560
￥88,001 total
includes taxes & fees
Sep 28 - Sep 29
Theater • Game Room • Gym • Firepit • 4BR Home
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

2. 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.
A quiet stay while you are away

3. 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)
Modern 3BR Apartment Near North Ave Shops

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

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is ￥17,145
￥52,500 total
includes taxes & fees
Sep 27 - Sep 28
Cozy Studio Suite, Steps from River North & Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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
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 ￥23,574
￥47,637 total
includes taxes & fees
Sep 28 - Sep 29
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a sectional sofa, a coffee table, and a TV.

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, 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 ￥28,575
￥36,530 total
includes taxes & fees
Oct 6 - Oct 7
Attractive Coach House Apartment for rent in Oak Park.
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 ￥30,004
￥54,158 total
includes taxes & fees
Oct 6 - Oct 7
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

8. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is ￥20,560
￥99,897 total
includes taxes & fees
Sep 29 - Sep 30
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A white two-story house with a porch, steps, and a small table with chairs.

9. 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 ￥32,544
￥86,327 total
includes taxes & fees
Sep 30 - Oct 1
Oak Park Victorian by FLW Studio

10. 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 ￥16,002
￥115,297 total
includes taxes & fees
Sep 30 - Oct 1
Arcade • Theater • Gym • Office • Sleeps 15
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, (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 ￥60,325
￥120,085 total
includes taxes & fees
Sep 28 - Sep 29
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

12. 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 ￥30,480
￥75,405 total
includes taxes & fees
Oct 15 - Oct 16
Classic Forest Park Foursquare < 1 Mi to Blue Line
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

13. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Bronzeville Gem: Balcony, Gym & Rooftop Deck
Near South Side
9.0 out of 10, Wonderful, (10 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
Bronzeville Gem: Balcony, Gym & Rooftop Deck
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

14. 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 ￥63,500
￥149,266 total
includes taxes & fees
Oct 5 - Oct 6
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (62 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,575
￥58,931 total
includes taxes & fees
Sep 28 - Sep 29
LUXE 3 BR, 2 BA + Hot Tub
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

16. 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 ￥41,434
￥97,947 total
includes taxes & fees
Sep 28 - Sep 29
Envitae Hotel, 4BR Modern Sleek Apartment
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

17. 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 ￥19,844
￥33,985 total
includes taxes & fees
Oct 25 - Oct 26
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A staircase with a wooden finish and black railings, leading to a room with a large wooden door and a white ceiling.

18. Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.8 out of 10, Exceptional, (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 ￥23,654
￥49,592 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Home by O'Hare + EV Plug
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥19,002
￥46,551 total
includes taxes & fees
Sep 28 - Sep 29
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
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
"Good property with friendly staff. J at the front desk was especially nice and helpful."
Alan 2-night trip
Posted 5 hours ago
Hampton Inn & Suites Chicago Medical District UIC

Find out more about West Side

West Side Vacation Homes information

Number of reviews
391
Accommodation
54 Vacation Homes
Lowest Price
￥33,985
Highest Price
￥149,266

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