A greenhouse with a glass ceiling, various cacti, and a wooden structure in the center.

Holiday Homes in West Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for West Side holiday homes

A circular fire pit with chairs around it, string lights overhead, and a house in the background.

1. Sleeps 18 • 7BR • Gym • Game Room • Theater

Sleeps 18 • 7BR • Gym • Game Room • Theater
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 NZ$1,860
includes taxes & fees
21 Sept - 22 Sept
Sleeps 18 • 7BR • Gym • Game Room • Theater

2. 4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
9.6 out of 10, Exceptional, (21 reviews)
"Very clean, very quite loved having 3 bathrooms, had everything you’d need for your stay"
Canada
LM
The price is NZ$1,259
includes taxes & fees
13 Sept - 14 Sept
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
A billiards room with multiple tables, large windows, and a high ceiling with exposed ductwork.

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

Wabash 4BR - Pool, Free In & Out Parking 1
Downtown Chicago
The price is NZ$507
includes taxes & fees
22 Sept - 23 Sept
Wabash 4BR - Pool, Free In & Out Parking 1

4. 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)
The price is NZ$1,263
includes taxes & fees
21 Sept - 22 Sept
Modern 3BR Apartment Near North Ave Shops
A modern balcony with a city view, a cushioned chair, a small table with a plant, and a potted plant on the floor.

5. ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.4 out of 10, Exceptional, (28 reviews)
"Beautiful place and location! Had a great time with my family here"
United States
Pedro C.
The price is NZ$1,317
includes taxes & fees
13 Sept - 14 Sept
ENVITAE Hotel, 4BR Luxury Modern Apartments
A living room with a sectional sofa, a round wooden coffee table, and three framed artworks on the wall.

6. 4BR Retreat w/ Theater, Arcade, Gym and Firepit

4BR Retreat w/ Theater, Arcade, Gym and Firepit
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 NZ$1,141
includes taxes & fees
22 Sept - 23 Sept
4BR Retreat w/ Theater, Arcade, Gym and Firepit
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

7. 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)
"Pros: Quiet neighborhood, felt safe going in and out of the house. Upstairs bathroom shower was amazing. Cons: warmer in living room, stained pillows, couches and floors felt like dust mites all over( simple fix) All in all it was a good stay."
United States
Amal
The price is NZ$519
includes taxes & fees
14 Sept - 15 Sept
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.

8. 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 NZ$392
includes taxes & fees
22 Sept - 23 Sept
Attractive Coach House Apartment for rent in Oak Park.
A modern building with a glass facade, surrounded by a courtyard with benches and greenery.

9. 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 NZ$1,419
includes taxes & fees
28 Sept - 29 Sept
Envitae Hotel, 4BR Modern Sleek Apartment
A single-story house with a covered porch, a front door, and a small garden area.

10. 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, (3 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is NZ$601
includes taxes & fees
6 Oct - 7 Oct
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A modern gym with various exercise equipment, including a bench press, dumbbells, and a treadmill.

11. Brand New 12 Bedroom Mansion

Brand New 12 Bedroom Mansion
Downtown Chicago
The price is NZ$6,726
includes taxes & fees
29 Sept - 30 Sept
Brand New 12 Bedroom Mansion
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

12. 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 NZ$1,067
includes taxes & fees
17 Sept - 18 Sept
Game Room • Fire-pit • Playground • Gym • Billiard
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

13. 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 NZ$830
includes taxes & fees
22 Sept - 23 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line

14. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
The price is NZ$1,329
includes taxes & fees
22 Sept - 23 Sept
Arcade • Theater • Gym • Office • Sleeps 15
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, (57 reviews)
"Hot tub was very nice!"
United States
Jeff
The price is NZ$637
includes taxes & fees
14 Sept - 15 Sept
LUXE 3 BR, 2 BA + Hot Tub
A white two-story house with a porch, steps, and a small table with chairs.

16. 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 NZ$1,064
includes taxes & fees
29 Sept - 30 Sept
Oak Park Victorian by FLW Studio
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (8 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 NZ$1,805
includes taxes & fees
16 Sept - 17 Sept
Sleeps 18 • 8BR • Game Room • Gym • Theater
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, (34 reviews)
"I had a fun stay "
United States
Jusu K.
The price is NZ$355
includes taxes & fees
14 Sept - 15 Sept
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A modern kitchen with stainless steel appliances, wooden cabinets, and a tiled backsplash.

19. 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
9.4 out of 10, Exceptional, (23 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is NZ$909
includes taxes & fees
22 Sept - 23 Sept
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
A beach with people sunbathing and swimming, a lighthouse, and a pier extending into the water.

20. 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, (192 reviews)
"Awesome house for family events. Great neighborhood and gathering space was great"
United States
Ann V.
The price is NZ$1,586
includes taxes & fees
5 Oct - 6 Oct
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top West Side Hotel Reviews

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

10/10 Excellent
"Chataun got us checked in and explained where everything was and what we could expect for the restaurant and breakfast along with parking. Our room was immaculate. Loved the balconies! We spent a lot of our time out there. Very close to great places to eat! Very impressed with the property and the restaurant Rye. The drinks were amazing and Ting took very good care of us at the bar. Recommend the margarita. Yum! If you’re going to Chicago and don’t want to stay in the hustle of downtown, this was a nice stay. Still close to plenty and convenient to motor ways."
Christina 1-night trip
Posted 5 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

West Side Holiday Homes information

Number of reviews
362
Accommodation
47 Holiday Homes
Lowest Price
NZ$355
Highest Price
NZ$1,860

Explore a world of travel with Expedia