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Featured Cottages in Far Southwest Side

"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...

"So cozy. Feels like staying in a guest house with the whole place to yourself! "

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Top Far Southwest Side Hotel Reviews

Freehand Chicago

10/10 Excellent

"The hotel was beautiful and unique, and the staff were friendly! We enjoyed the cocktail lounge on the first floor. My only complaint is that our Air Conditioning unit didn’t work, but we also didn’t bring that to the attention of the front desk because we had reservations somewhere and weren’t back until late, so I can’t really complain!"