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

"Great house, great neighborhood, host was amazing!"

"Booked this place as we had a concert at Wrigley Field. The owner was phenomenal. 100% advertised. Great place to stay. 10 out of 10 would book again if in the area."

"The building is from the 19th century which made it a really unique experience. The hosts were amazing and quick to respond. We went to check out the Linkin Park concert in the United Center and it was a 5min walk from the property. "

"The house had a lot of gnats and we were bit up"

includes taxes & fees

30 Sept - 1 Oct

"Comfy beds and a great house for kids and adults."

includes taxes & fees

28 Oct - 29 Oct

"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "

"Excellent place to stay and host provided great communication. The house is very nice and we also enjoyed the fire pit and hot tub, too! We highly recommend staying at this house and we will be back soon!"

"very nice four bedroom home and a great location."

"We loved Retro House, a real treasure inside Chicago. Comfortable, quiet and safe."

"Clean, comfortable, and secure"

includes taxes & fees

7 Oct - 8 Oct

"Great"

"We had a fantastic experience staying here. The layout was spacious and worked perfectly for our group of 10 adults—plenty of room for everyone to relax and spread out. The home was clean, well-kept, and exactly as described. Check-in and check-out were a breeze, and the neighborhood was quiet and welcoming with easy access to public transportation, which made getting around simple. Overall, a 10/10 stay—we really enjoyed our time and would definitely book again!"

"The house was spacious and perfect for our large group. "

"Beautiful, quiet space."

includes taxes & fees

12 Oct - 13 Oct

"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "

"We enjoyed our stay"

includes taxes & fees

21 Oct - 22 Oct

includes taxes & fees

6 Oct - 7 Oct

"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"

includes taxes & fees

30 Sept - 1 Oct