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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for West Side vacation homes

A cozy outdoor seating area with Adirondack chairs around a fire pit, string lights overhead, and a house in the background.

1. Firepit • Game Room • Theater • Gym • Sleeps 18

Firepit • Game Room • Theater • Gym • Sleeps 18
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 ￥27,609
￥152,983 total
includes taxes & fees
Oct 29 - Oct 30
Firepit • Game Room • Theater • Gym • Sleeps 18
A modern kitchen with grey cabinets, a stainless steel microwave, a black refrigerator, and a dishwasher.

2. Quiet Area - Revamped Basement

Quiet Area - Revamped Basement
Belmont Cragin
9.0 out of 10, Wonderful, (2 reviews)
"Excellent apartment very clean and comfortable. "
United States
Albert
The price is ￥17,569
￥69,557 total
includes taxes & fees
Oct 29 - Oct 30
Quiet Area - Revamped Basement
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveler
The price is ￥21,585
￥143,748 total
includes taxes & fees
Oct 27 - Oct 28
Sleeps 18 • 8BR • Game Room • Gym • Theater
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

4. 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 ￥17,943
￥95,030 total
includes taxes & fees
Nov 2 - Nov 3
Theater • Game Room • Gym • Firepit • 4BR Home
A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

5. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our group! There was more than enough space. The host let us drop our luggage off early since we arrived in the area before 4. The listing initially had errors, but the host updated the listing and we knew what to expect coming into it. Thank you for a wonderful stay!"
United States
Jamiee B.
The price is ￥19,334
￥105,034 total
includes taxes & fees
Oct 27 - Oct 28
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

6. 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 ￥33,602
￥94,855 total
includes taxes & fees
Nov 1 - Nov 2
Chicago Riverhouse with private fenced in oasis
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

7. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (12 reviews)
"Wonderful place to stay!"
United States
Chasity D.
The price is ￥36,080
￥111,542 total
includes taxes & fees
Nov 9 - Nov 10
Vibrant House, Walk to Train, Game Room
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ￥19,930
￥47,721 total
includes taxes & fees
Nov 4 - Nov 5
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

9. 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
9.6 out of 10, Exceptional, (4 reviews)
"This property fully met our needs for our weekend trip to the Chicagoland area to visit family in Westmont and explore the city. Finding an affordable, conveniently located, and pet friendly location was a major concern on this trip…finding this property relieved all of our concerns."
United States
Chad R.
The price is ￥26,668
￥42,228 total
includes taxes & fees
Nov 9 - Nov 10
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a dining area, a sofa set, and a television mounted on the wall.

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 ￥23,611
￥125,065 total
includes taxes & fees
Nov 2 - Nov 3
Arcade • Theater • Gym • Office • Sleeps 15
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

11. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (89 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is ￥16,801
￥32,603 total
includes taxes & fees
Oct 27 - Oct 28
Master qtr close to nature & easy urban facilities
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

12. 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, (35 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is ￥23,295
￥47,577 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a white armchair, a coffee table, and a TV. There is a kitchen area in the background with a dining table and chairs.

13. Cozy Home | King Bed | 10P | Metra |Chicago Suburb

Cozy Home | King Bed | 10P | Metra |Chicago Suburb
Highland Hills
9.4 out of 10, Exceptional, (3 reviews)
"I booked this property because I was told (before I made the reservation) that the bedroom and one of the bathrooms were on the main floor. I specifically inquired whether my mother-in-law would need to use stairs to access a bedroom and bathroom. In the words of the host, "the main living area, kitchen, two bedrooms and a full bathroom are on the main floor. Only the basement requires the use of steps ". This was not the case. The two bedrooms and a full bathroom are up a flight of 5...
United States
Denise G.
The price is ￥15,530
￥62,083 total
includes taxes & fees
Nov 18 - Nov 19
Cozy Home | King Bed | 10P | Metra |Chicago Suburb
A single-story house with a covered porch, a front door, and a small garden area.

14. 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 ￥29,507
￥53,353 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

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
9.6 out of 10, Exceptional, (25 reviews)
"Great place Great location "
United States
Josh W.
The price is ￥22,566
￥62,908 total
includes taxes & fees
Oct 27 - Oct 28
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

16. Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking

Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
Oak Park
The price is ￥26,668
￥60,342 total
includes taxes & fees
Oct 27 - Oct 28
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

17. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveler
The price is ￥28,237
￥58,402 total
includes taxes & fees
Oct 28 - Oct 29
LUXE 3 BR, 2 BA + Hot Tub
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (4 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 ￥30,759
￥97,890 total
includes taxes & fees
Nov 1 - Nov 2
Game Room • Fire-pit • Playground • Gym • Billiard
A backyard with a barbecue grill, a dining table with chairs, and a fire pit.

19. PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.4 out of 10, Exceptional, (36 reviews)
"This property was perfect for our weekend stay in the Chicagoland area. It was conveniently located to activities, shops and restaurants. Vic is a wonderfully attentive host who responds quickly and is happy to answer any questions or concerns."
United States
Christine M.
The price is ￥19,930
￥46,391 total
includes taxes & fees
Oct 29 - Oct 30
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
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, (36 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ￥22,448
￥32,698 total
includes taxes & fees
Oct 27 - Oct 28
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

Hotel Chicago West Loop, SureStay Collection by Best Western

Hotel Chicago West Loop, SureStay Collection by Best Western

8/10 Good
"Best place to stay for walking distance to an event at the United Center. It is not the Ritz but it is serviceable, the staff is helpful, there is good local dining and parking, and it was ok for our purpose."
Richard 2-night trip
Posted 1 hour ago
Hotel Chicago West Loop, SureStay Collection by Best Western

Find out more about West Side

West Side Vacation Homes information

Number of reviews
370
Accommodation
54 Vacation Homes
Lowest Price
￥32,603
Highest Price
￥152,983

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