Holiday Homes in Southwest Side

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Featured Holiday Homes in Southwest Side

"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

29 Sept - 30 Sept

"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!"

"Nice property easy check in. Experience was amazing. Thank you again "

includes taxes & fees

6 Oct - 7 Oct

"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!"

"Great place for our large group. Lots of room for the bridal girls to get ready for the wedding. "

"We enjoyed our stay"

includes taxes & fees

29 Sept - 30 Sept

"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

29 Sept - 30 Sept

"Great location that was walking distance to everything we needed. There was more than enough room for our group and it was a comfortable stay."

"I would recommend to anyone. "

"Perfect for what we needed!"

includes taxes & fees

29 Sept - 30 Sept

"So we never stayed on this property. Or was suppose to be canceled but the host never canceled are reservation.Granted my credit card was flagged for fraud once I tried to book it, once it was cleared I tried to again, dates were not available so I told Farrah the host we needed to cancel & I will look for other places. Her response, no problem. But come to find out it wasn’t canceled, we did not stay here. Had another property in St Charles..lovely place with great communication from the host....