Holiday Homes in West Side

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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Featured Holiday Homes in West Side

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Fridge, microwave, oven, stovetop

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

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"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
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Private kitchen

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

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
Terrace/patio

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Interior

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
Vital Urban: Spa Inspired Retreat
Terrace/patio

Vital Urban: Spa Inspired Retreat

10.0 out of 10, Exceptional, (2)
"All the comforts of home with the amenities of a resort! Communication with the host was stellar. We had an amazing stay and look forward to booking again!"
Vital Urban: Spa Inspired Retreat
Cabin 308 by 747 Lofts
Exterior

Cabin 308 by 747 Lofts

9.4 out of 10, Exceptional, (14)
"Nice place, interesting neighborhood. Very convenient location!"
Cabin 308 by 747 Lofts
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Pool

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
Designer Smart Home- Wicker Park
Fridge, microwave, oven, stovetop

Designer Smart Home- Wicker Park

Designer Smart Home- Wicker Park
Charming 3-bedroom house in awesome Chicago with AC, WiFi
Private kitchen

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

Charming 3-bedroom house in awesome Chicago with AC, WiFi
Spacious 5 BR / King Size Beds + Private Parking!
Property grounds

Spacious 5 BR / King Size Beds + Private Parking!

9.4 out of 10, Exceptional, (10)
"The stay was good. Although the areas around the home is really rough and its next to an abandoned home that's boarded up. When we arrived, it was shocking and we almost thought we were at the wrong place. Nonetheless, we still enjoyed the home and Jonathan was a pleasure to work with. "
Spacious 5 BR / King Size Beds + Private Parking!
ART Downtn Fulton Market-3 bdrm HOME-EVTesla Private Grge-Sleeps 10-Rooftop-Pets
Miscellaneous

ART Downtn Fulton Market-3 bdrm HOME-EVTesla Private Grge-Sleeps 10-Rooftop-Pets

10.0 out of 10, Exceptional, (1)
"My family and I had a wonderful weekend in Chicago, all thanks to your beautiful home. We comfortably slept four people and enjoyed the ample space. The house is filled with stunning natural light during the day, thanks to the full windows on the second floor and a skylight in the stairwell leading to the third floor. One of the features we loved the most was the parking and the use of the garage. The kitchen was easy to navigate, and we appreciated the selection of coffee available."
ART Downtn Fulton Market-3 bdrm HOME-EVTesla Private Grge-Sleeps 10-Rooftop-Pets
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover
Fridge, microwave, oven, dishwasher

Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

8.8 out of 10, Excellent, (5)
"The location ( Target around the corner and lots of walkable shops and restaurants) and the parking are amazing, and the home has lots of space and beds. We held our staff retreat (we are a non-profit with employees in multiple states and no office). and it was very comfortable. We used the huge dining table for some meetings and others in the den upstairs where we could connect to the tv for a few presentations (brought my own HDMi cable). The kitchen is huge and well stocked except for having...
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (19)
"Beautiful home in great location. Host was very responsive and we had no issues "
Stunning MODERN Home Downtown/RiverWest Close to Fulton Market & United Center
Luxe SFH Bucktown Retreat with Garage Parking
Fridge, microwave, oven, stovetop

Luxe SFH Bucktown Retreat with Garage Parking

9.4 out of 10, Exceptional, (10)
"The house is in a very good location, shops, transportation and restaurants all close by. All of the rooms and bathrooms are comfortable and updated. We did a mix of take out and cooking and everything was great."
Luxe SFH Bucktown Retreat with Garage Parking
MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!
Private kitchen

MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!

10.0 out of 10, Exceptional, (8)
"Oba was very communicative and responsive to questions and we loved the recommendations for food in the area. While others have noted that this isn't the best neighborhood we were never disturbed and its closeness to the Pink Line to get downtown was super convenient. We had a larger group and all of the beds and linens were adequate, and we appreciated all the labels around the unit to make things easy to find.I think my only note - you need better photos! Rooms were much more spacious than...
MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
Beach

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

9.8 out of 10, Exceptional, (6)
"My husband and I really enjoyed our stay. The hosts were very easy to communicate with and the home is perfectly located within walking distance to many shops and restaurants. Wicker Park is a wonderful neighborhood!The home was very comfortable and clean! We will stay again, next time we are in Chicago!"
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)
Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom
Private kitchen

Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom

10.0 out of 10, Exceptional, (1)
Level Fulton Market - Open Concept studio with full kitchen and luxury bathroom
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Outdoor dining

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

10.0 out of 10, Exceptional, (6)
"Stayed here with six others for a girls trip.The house was beautifully decorated, beds were comfy, and the backyard was such a nice spot to hang out in during our downtime. We loved how much space we had and the attention to the vibes. Adam was super helpful and responsive before and during our stay. We all wished our trip was longer!"
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Terrace/patio

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

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
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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Other property types in West Side

Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (257)
"wonderful easy accessible ideal for people have stsycation"
The price is NZ$230
includes taxes & fees
13 Mar - 14 Mar
Sonder Market Hall
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (140)
"My unit was very nice and more than perfect for my needs. It was spacious and quiet. There is little going on in the area in the evenings which I found a bit unnerving as an older adult. You know - there's safety in numbers! "
The price is NZ$256
includes taxes & fees
23 Feb - 24 Feb
Sonder The Burnham Apartments
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (132)
"The suite was amazing - the decor was beautiful and it was well equipped with everything I needed for a longer stay. The coffee machine and local freshly ground coffee was a nice touch. The bed was incredibly comfortable too. There were a few tiny issues with the room - the water pressure in the shower was really poor making hair washing feel like a chore and there were no tea spoons which made stirring coffee or eating a yogurt kind of comical. However, neither of these were deal breakers for...
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.