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

Holiday Homes in Chicago

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Featured Holiday Homes in Chicago and around

1 bedroom, iron/ironing board, travel cot, WiFi

"The apartment looked exactly like the pictures and was very well kept. Everything was clean and functional and we didn’t have any issues. The neighborhood is very quiet and safe and also has a target nearby for quick grocery trips. Connectivity wise, there’s a busy stop within walking distance but no train stations.The host was also very responsive and helpful. We didn’t have any trouble checking in or checking out.Overall a great experience and comfortable stay."

includes taxes & fees

17 Jul - 18 Jul

Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and microwave.

includes taxes & fees

16 Jul - 17 Jul

Enjoy cooking in this kitchen with a gas stove, oven, and microwave, complemented by dark cabinetry.

includes taxes & fees

17 Jul - 18 Jul

includes taxes & fees

27 Jul - 28 Jul

Experience the grandeur of our lobby, featuring a central fountain, plush seating, and intricate woodwork.

includes taxes & fees

11 Aug - 12 Aug

Classic Chicago hotel with a symmetrical facade, large windows, and a central entrance.

includes taxes & fees

10 Aug - 11 Aug

Relax on the deck with four Adirondack chairs and a grill station.

"This was one of our favorite places we have ever stayed! It was clean, decorated beautifully, had comfortable beds, a refrigerator with an ice maker and filtered water, washer and dryer that worked great, a cool backyard with hammocks, and even little things like coffee creamer, toothpaste, and mouthwash in case you forgot yours. We stayed in three different rental places on our trip and this was by far our favorite! What a beautiful home! "

includes taxes & fees

14 Jul - 15 Jul

Relax in this inviting bedroom with a comfortable bed, sofa, and lush greenery.

"I thought I was in a $300 night hotel, private, and serene surrounding"

includes taxes & fees

14 Jul - 15 Jul

Kitchen features a gas stove, oven, and sink, with a colorful tile backsplash and window.

"Lovely little cottage in great location with excellent restaurants close by. Had everything we needed for our stay. Kitchen was perfectly equipped and having the washer dryer was such a bonus. The communication with the landlord was very good. Would absolutely stay here again. "

includes taxes & fees

15 Jul - 16 Jul

includes taxes & fees

27 Jul - 28 Jul

includes taxes & fees

27 Jul - 28 Jul

Stunning two-story building with a gabled roof and evenly spaced windows, set amidst a beautifully maintained lawn and garden.

"We stayed a few nights and everything was nice and clean. Thank you!"

includes taxes & fees

15 Jul - 16 Jul

includes taxes & fees

27 Jul - 28 Jul

Stunning home with a covered porch, large windows, and beautifully landscaped yard.

"Great spot."

includes taxes & fees

14 Jul - 15 Jul

Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

"Great experience, lots of cooking materials "

includes taxes & fees

20 Jul - 21 Jul

includes taxes & fees

27 Jul - 28 Jul

Fridge, oven, stovetop, coffee/tea maker

"The area is quiet and the apartment is close to a dog park which is open to non-residents. There is a paved walkway right by the park that’s nice so I was able to walk my dog in the morning. The property manager immediately replied to any questions I had and the apartment was fully stocked in the kitchen, etc. I booked this because of the cost. I was in town to see the Indiana Dunes. I would stay here again."

includes taxes & fees

26 Jul - 27 Jul