Search Private Holiday Homes in Southwest Side

    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
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Private Holiday Homes in Southwest Side

Spacious Retreat Near Convention Centers 4 Bedroom Home by RedAwning
Relax in this stylish living room with a grey sofa, round coffee table, and large flat-screen TV.

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
Charming Contemporary Family Home 3 Bedroom Home by RedAwning
Features a sleek kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

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
Stunning two-story home with a brick facade, central entrance, and covered porch.

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
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
Enjoy meals in the spacious kitchen with a large island, stove, and ample counter space.

Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover

3.0 star property
Charming Oak Park 4BD/3.5BA and 2 Private Parking by AllSet Turnover
6 Bed Whole House In Chicagolands Trendy Berwyn 6 Bedroom Home by AllSet Turnover
Relax on the enclosed porch with a wooden bench and single chair, offering a view of the surrounding neighborhood.

6 Bed Whole House In Chicagolands Trendy Berwyn 6 Bedroom Home by AllSet Turnover

3.0 star property
6 Bed Whole House In Chicagolands Trendy Berwyn 6 Bedroom Home by AllSet Turnover
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free