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Featured Vacation 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
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.
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Top Southwest Side Hotel Reviews

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"Great location, staff and view! "
Kimberley 1-night trip
Posted 2 hours ago
Hyatt Regency Chicago