Holiday Homes in West Side

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in West Side

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (12)
"We have a good time in this property. It is very well located to go to the United Center and to downtown Chicago."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Spacious and Sleek 4BD/2.5BA - Logan Square!

9.4 out of 10, Exceptional, (18)
"Overall, we had a great time in Chicago. The area was perfect and it’s located right across a school so it made it a bit more entertaining when seating out in the balcony. The home had all we looked for and was very much pretty clean. Nice place to stay and will definitely reconsider for our next stay. "
Spacious and Sleek 4BD/2.5BA - Logan Square!

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (117)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Chicago West Town Row House

2.0 star property
8.0 out of 10, Very good, (1)
"Would use this property again, was very cute and interesting lay out. "
Chicago West Town Row House

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (89)
"We stayed at the property for a bachelorette party weekend. The house was very nice and the host was so accommodating! The coffee maker was also a big plus. Highly, highly recommend for a large group! Great stay! "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Private Historic Coach House Wicker Park

10.0 out of 10, Exceptional, (59)
"This is our third stay at the Coach House, and we hope to come back again! The property is well appointed, comfortable, clean and has everything you need. The location is perfect and the hosts, Mark and JoAnne and very responsive, thoughtful and accommodating. A definite 10/10. "
Private Historic Coach House Wicker Park

Charming 3-bedroom house in awesome Chicago with AC, WiFi

Charming 3-bedroom house in awesome Chicago with AC, WiFi

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (46)
"The place worked great for our family to get together. The host was very prompt in responding and the place was just as described. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

NEW Contemporary Home - 5BR/3.5BA+office+garage

9.0 out of 10, Wonderful, (9)
"The property was in an excellent location for visiting the hospital, IIT and Lincoln Park Zoo. Our group of 9 had plenty of space and the 2-car garage was very helpful!"
NEW Contemporary Home - 5BR/3.5BA+office+garage

Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

10.0 out of 10, Exceptional, (28)
"Located in a nice part of town. Right next to the highway but you can barely hear any street noise from inside. Comfy beds, easy communication with owner. Located near a couple nice bars and restaurants that are walkable and the blue line is also really close. Plan on staying here again in the future!"
Beautiful Designer Townhome ~ Amazing Location! River West - 4-Bedroom / Unit 1

Luxury Modern home minutes from Downtown Chicago

10.0 out of 10, Exceptional, (13)
"My friends and I love the neighborhood and how the house was perfectly set up for cosy conversation and hanging out. "
Luxury Modern home minutes from Downtown Chicago

Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center

9.8 out of 10, Exceptional, (20)
"Loved the property and location. The host was very communicative and accommodating. Would stay here again!"
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

7.0 out of 10, Good, (2)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

5 Mi to Millennium Park: Apartment w/ Fireplaces

9.8 out of 10, Exceptional, (10)
"All said!"
5 Mi to Millennium Park: Apartment w/ Fireplaces

Vital Urban: Spa Inspired Retreat

10.0 out of 10, Exceptional, (3)
"Beautiful home! Very clean and had everything we that might need. Would recommend."
Vital Urban: Spa Inspired Retreat

Welcome to Lux! 2BR in Chicago!

Welcome to Lux! 2BR in Chicago!

Wicker Park Entire House, Private Yard and Parking!

10.0 out of 10, Exceptional, (10)
"Great house, yard and location. Felt very much at home. Had everything you needed. Will definitely recommend this property and come back "
Wicker Park Entire House, Private Yard and Parking!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

9.8 out of 10, Exceptional, (9)
"My family and I loved the space. It was a nice home to retreat back to after touring the city. The amenities were wonderful and we loved watching a movie on the top floor. It had a great view of the city. "
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
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.
Don't see what you're looking for?
See all available properties in West Side
Save an average of 15% on thousands of hotels when you're signed in

Other property types in West Side

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (277)
"Charming, minimalist, accessible and modern, just what I needed, ideal for couples or single people who want to enjoy the city."
The price is NZ$269
includes taxes & fees
26 May - 27 May
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
9.0 out of 10, Wonderful, (163)
"Easy and great for extended stay."
The price is NZ$282
includes taxes & fees
27 May - 28 May
Sonder The Burnham Apartments

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (154)
"Great place to stay. Super designer interior. A great location in Little Italy with so many options for local eating and drinking. Good buses to downtown. Highly recommended. "
The Neighborhood Hotel-Little Italy
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.