Chicago which includes a high-rise building and a city as well as a family

Holiday Homes in Chicago

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Featured Holiday Homes in Chicago

Enjoy cooking in this well-equipped kitchen with a stainless steel range hood and a central sink.

"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "

Enjoy cooking in this well-equipped kitchen with a double sink, oven, and dishwasher.

"Great Place. Super area!"

"Very nice place "

includes taxes & fees

11 Aug - 12 Aug

Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "

Enjoy meals in this dining area with a wooden table, white chairs, and a large mirror.

"Great place"

includes taxes & fees

20 Aug - 21 Aug

Enjoy cooking in this well-equipped kitchen with a central island, sink, and stainless steel appliances.

includes taxes & fees

4 Aug - 5 Aug

Stunning single-family home with a backyard surrounded by mature trees and a well-manicured lawn.

"The home was clean and Maggie was very responsive in our chat when I needed something. Very lovely. "

Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."

"Loved the place and host was super helpful when needed! "

Sit on the porch and enjoy the serene surroundings.

"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "

includes taxes & fees

4 Aug - 5 Aug

Relax by the fire pit in this serene outdoor space, surrounded by comfortable seating and lush greenery.

"Lots of good food and close to transit! Amazing little spot."

Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, and dishwasher.

"Property manager was very responsive and the communication was clear and helpful. The house was very clean. Although the neighborhood was very concerning, dirty with a lot of people standing on the block, no one was threatening and nothing happened during our stay. Parking on street was safe. "