Holiday Homes in West Side

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan

Our top choices for West Side holiday 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 €797
includes taxes & fees
9 Nov - 10 Nov
Firepit • Game Room • Theater • Gym • Sleeps 18
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

2. 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 traveller
The price is €762
includes taxes & fees
9 Nov - 10 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

3. 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 €514
includes taxes & fees
19 Nov - 20 Nov
Chicago Riverhouse with private fenced in oasis
A dining room with a wooden table, black chairs, a red placemat, and a ceiling light fixture.

4. 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 €329
includes taxes & fees
7 Nov - 8 Nov
Bright & Spacious Oak Park Getaway 2BR, 1.5BA + Covered Garage Parking
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is €433
includes taxes & fees
9 Nov - 10 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
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

6. 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 €551
includes taxes & fees
9 Nov - 10 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €266
includes taxes & fees
1 Dec - 2 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

8. 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 €262
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

9. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
The price is €598
includes taxes & fees
11 Nov - 12 Nov
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

10. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

11. 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, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €234
includes taxes & fees
4 Dec - 5 Dec
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A single-story house with a covered porch, a front door, and a small garden area.

12. 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 €376
includes taxes & fees
10 Nov - 11 Nov
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

13. 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 traveller
The price is €320
includes taxes & fees
19 Nov - 20 Nov
LUXE 3 BR, 2 BA + Hot Tub
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

14. 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, (45 reviews)
"Great location. Great place to stay. "
United States
Jill L.
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern house with a covered porch, large windows, and a well-maintained garden with various plants and flowers.

15. Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (90 reviews)
"Great spot, safe, clean, and beautiful environment would highly recommend!"
United States
Chris F.
The price is €180
includes taxes & fees
10 Nov - 11 Nov
Master qtr close to nature & easy urban facilities
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.

16. 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.
Cozy Home | King Bed | 10P | Metra |Chicago Suburb
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

17. 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
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is €295
includes taxes & fees
8 Nov - 9 Nov
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A wooden deck with a railing, a staircase, and a window with a wreath.

18. 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, (37 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €178
includes taxes & fees
19 Nov - 20 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

19. 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 €395
includes taxes & fees
9 Nov - 10 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A white two-story house with a porch, steps, and a small table with chairs.

20. 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 €526
includes taxes & fees
10 Nov - 11 Nov
Oak Park Victorian by FLW Studio
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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A building with a sign reading "GARDEN BABY CONSERVATORY" and a red door.

Top reviews in West Side

A grand hotel facade with classical architecture, featuring tall columns, ornate detailing, and a prominent entrance with a marquee.
Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District

Hyatt House Chicago Medical/University District
Near West Side

8/10 Good

Room was clean and spacious. Breakfast offered a wonderful selection. Staff were very friendly and helpful. It takes a day to adjust to hearing sirens but that's to be expected in this area. Lovely walk to the river (approx 1hr) or a two minute walk to the train, so very easy to commute.
Ireland
Natasha
Reviewed May 10, 2026
Hyatt House Chicago Medical/University District

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