Chicago Staycation Rentals
Location
Travel Dates
Guests
AS SEEN IN
Plan your staycation in Chicago
Enjoy the perfect local escape with our Chicago staycation rentals. Whether you're looking for a trendy downtown loft, a cozy apartment in Lincoln Park, or a lakefront retreat, we have the perfect options for your staycation. Explore the city’s famous attractions, hidden gems, and dining spots while relaxing close to home. Book your Chicago staycation with Whimstay and rediscover the Windy City in style!
Top Chicago staycation rentals
Popular features and amenities
Pet Friendly
Children Welcome
Heating
Dryer
Kitchen
Iron and board
Hair dryer
Air conditioning