Search Private Holiday Homes in Southwest 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

In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
In three months
19 Dec - 21 Dec

Featured Private Holiday Homes in Southwest Side

Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Private kitchen

Charming Contemporary Family Home 3 Bedroom Home by RedAwning

3.5 star property
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Exterior

Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning

3.0 star property
Serene & Charming 5br Des Plaines Getaway 5 Bedroom Home by RedAwning
Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Living area

Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning

3.5 star property
10.0 out of 10, Exceptional, (1)
"Everything was great!! "
Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Modern Retreat With Private Pool & Yard 3 Bedroom Home
Private kitchen

Modern Retreat With Private Pool & Yard 3 Bedroom Home

3.0 star property
Modern Retreat With Private Pool & Yard 3 Bedroom Home
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 Southwest Side Hotel Reviews

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"good"
Blanca 3-night trip
Posted 2 days ago
InterContinental Chicago Magnificent Mile by IHG

Find out more about Southwest Side

Find out more about Southwest Side

Southwest Side Private Holiday Homes information

Number of reviews
Accommodation
5 Private Holiday Homes
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia