Holiday Homes in West Side

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Featured Holiday Homes in West Side

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

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

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (122)
"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "
Luxury Home Away From Your Home

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

8.0 out of 10, Very good, (5)
"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!

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (4)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped

Spacious 5-bedroom house great for large groups

Spacious 5-bedroom house great for large groups

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
9.0 out of 10, Wonderful, (7)
"We got all the help and instructions needed to easily find this clean, well-supplied apartment with lovely outdoor space attached. And with the Pink Line just a few minutes walk and The Loop just 6 stops away, it was the perfect home base for getting to all that Chicago has to offer!"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

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

9.2 out of 10, Wonderful, (22)
"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 Modern home minutes from Downtown Chicago

10.0 out of 10, Exceptional, (14)
"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

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

9.0 out of 10, Wonderful, (6)
"Very convenient to the Metra blue line, lots of bars and restaurants in the neighborhood. "
Wicker Park 6bd/4ba, Steps from CTA, Parking Incl by AllSet Turnover

Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage

10.0 out of 10, Exceptional, (3)
"The host was awesome, very cooperative and amazing at communication ! The house also was perfect, super spacious and clean. Had a great stay with my cousins!"
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage

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

10.0 out of 10, Exceptional, (90)
"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

Chic Chicago Retreat (2-Bedroom Home) by RedAwning

10.0 out of 10, Exceptional, (1)
"Great place to find last minute. Very helpful hosts and a nice place to stay"
Chic Chicago Retreat (2-Bedroom Home) by RedAwning

Charming 3-bedroom house in marvelous Ukrainian village Chicago

6.0 out of 10, (2)
"We enjoyed our stay, especially the location of the neighborhood."
Charming 3-bedroom house in marvelous Ukrainian village Chicago

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (13)
"The house was excellent for our family. It was definitely enough room and everything was okay for our trip. Neighborhood was nice and no one bothered us. "
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Wicker Park Haven. 3-Levels. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage

10.0 out of 10, Exceptional, (23)
"Nancy was a great host and she place was even better!"
Wicker Park Haven. 3-Levels. 12Beds.10min walk to Train. Rooftop+Spa Bath+Garage

EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

9.8 out of 10, Exceptional, (19)
"Beautifully maintained property in residential neighborhood proximate to fantastic food and beverage / public transportation and quick cab ride from all major Chicago attractions. "
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE

MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

8.6 out of 10, Excellent, (7)
"For friends traveling to Chicago this is the perfect layout for privacy, modern amenities and a wonderful place to relax. Highly recommend for its location and accommodation."
MODERN DOWNTOWN 5-LEVEL-HOME WITH ROOFTOP AND 360-DEGREES SKYLINE VIEWS

Private Historic Coach House Wicker Park

10.0 out of 10, Exceptional, (62)
"Highly recommend this stay. Was spotless, professionally stocked and overall an amazing experience. Mark and Joanne were responsive to our needs and we had a great stay. "
Private Historic Coach House Wicker Park

Spacious 4-Level/4-Bedroom Townhouse in West Loop

10.0 out of 10, Exceptional, (57)
"Excellent property, excellent location, excellent host!"
Spacious 4-Level/4-Bedroom Townhouse in West Loop

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

10.0 out of 10, Exceptional, (2)
"Spacious and clean property in a great location. "
Stunning 4-bedroom 4-bath building in Wicker Park! + Parking
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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