Holiday Homes in West Side

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
10 Oct - 12 Oct
In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov

Featured Holiday Homes in West Side

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Property grounds

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony

9.2 out of 10, Wonderful, (55)
"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
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!
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Terrace/patio

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

2.0 star property
9.0 out of 10, Wonderful, (9)
"Great"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Fridge, microwave, oven, stovetop

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (12)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped
Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home
Fridge, microwave, oven, stovetop

Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home

6.0 out of 10, (5)
"I rented this house for my family who came for my son's wedding. MANY issues, including serious safety concerns! I emailed the owner with a list that included the following: ~ WATER WAS HOT ENOUGH TO SCALD! ~ Upstairs hall bathroom - no t.p. holder, bathmat, towel bar & only one hook for 8 people to share. Toilet seat broke on the first day. Toilet seat in master bathroom didn't fit, one hinge was broken. ~No dressers in any bedrooms - no place to put personal items. Small plastic (one broken)...
Heart of Chicago 5 Bedroom Modern 12 guest West Bucktown Home
Spacious 5-bedroom house great for large groups
Fridge, microwave, oven, stovetop

Spacious 5-bedroom house great for large groups

10.0 out of 10, Exceptional, (1)
Spacious 5-bedroom house great for large groups
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Exterior

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

10.0 out of 10, Exceptional, (91)
"Awesome location, plenty of space, timely communication, clean. We loved it!"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
Fridge, microwave, oven, stovetop

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
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

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
Luxury Home Away From Your Home
Fridge, microwave, oven, stovetop

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (131)
"Friendly Neighbors and house was clean with fenced around the house and back parking lot! Was able to use the grill and location is near the locations we planned to go!"
Luxury Home Away From Your Home
Chic Chicago Retreat (2-Bedroom Home) by RedAwning
Exterior

Chic Chicago Retreat (2-Bedroom Home) by RedAwning

8.0 out of 10, Very good, (3)
"Overall the house was nice and in a quiet area. My only negative feedback would be finding a parking. Other than that we enjoyed our stay."
Chic Chicago Retreat (2-Bedroom Home) by RedAwning
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
Property grounds

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (8)
"Beautiful house! We came to Chicago for my son’s graduation and it was the perfect location and size for our whole family to stay and enjoy!! "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym
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, (14)
"My group of friends enjoyed our stay at this property for a concert in downtown Chicago. Oba was extremely communicative before, during and after our stay. Transportation via rideshare was easy (minus rush hour traffic). Would definitely stay here again!"
MODERN HOME: 4BD & 3 FULL BATHS, WFH Setup, Public Transit, 15 Mins to Downtown!
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
Outdoor dining

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

10.0 out of 10, Exceptional, (13)
"Good"
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (23)
"The property was great and accommodated 11 people nicely "
EAST VILLAGE 4-LEVEL-HOUSE WITH 5 BATHS & COVERED ATTACHED GARAGE
Wicker Park Entire House, Private Yard and Parking!
Terrace/patio

Wicker Park Entire House, Private Yard and Parking!

10.0 out of 10, Exceptional, (13)
"We came into town for some weekend parties. It was a great location and we were all comfortable. Nice place"
Wicker Park Entire House, Private Yard and Parking!
Private Historic Coach House Wicker Park
Fridge, microwave, oven, stovetop

Private Historic Coach House Wicker Park

10.0 out of 10, Exceptional, (65)
"Our family had a fantastic stay at Mark and JoAnn's lovingly appointed vacation rental. It is located in the heart of Whicker Park and all the area has to offer, and an easy 10-minute walk to the Blue Line for getting anywhere else. The four of us stayed for five days and found their unit extremely clean, comfortable, and very quiet. We don't sleep well with city noise, so we are thrilled to have found a place close to everything but tucked away on a quiet neighborhood street. The bedding was...
Private Historic Coach House Wicker Park
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Fridge, microwave, oven, stovetop

Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer

2.0 star property
9.8 out of 10, Exceptional, (6)
"This is indeed a cozy 1-bedroom house. It has been remodeled and is very attractive and comfortable. We will stay here again when we visit family in the Wicker Park area."
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer/Dryer
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
Outdoor dining

Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover

10.0 out of 10, Exceptional, (3)
"My new go to spot to stay in Chicago. Really loved the space and location, easy to get around. "
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
Modern SFH Near McCormick Place & Soldier Field
Fridge, microwave, oven, stovetop

Modern SFH Near McCormick Place & Soldier Field

10.0 out of 10, Exceptional, (11)
"As a group of family and friends this was a great property"
Modern SFH Near McCormick Place & Soldier Field
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
"clean"
Trpimir 5-night trip
Posted 7 hours ago
Crowne Plaza Chicago West Loop by IHG

Find out more about West Side

Find out more about West Side

West Side Holiday Homes information

Number of reviews
458
Accommodation
68 Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia