Southwest Side Holiday Rentals - Holiday Homes in Southwest Side

Check Southwest Side vacation rental availability

Vacation Rentals in Southwest Side

"Staff is friendly and very helpful!"

P9,138 total

includes taxes & fees

Dec 10 - Dec 11

"Easiest check in and check out process "

P5,587 total

includes taxes & fees

Dec 24 - Dec 25

"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."

P9,832 total

includes taxes & fees

Dec 23 - Dec 24

49-inch Smart TV with digital channels, TV, streaming services

"Had a great stay at Kasa! The place had everything necessary to make ourselves right at home. 10/10 looking forward to coming back in the future! "

50-inch Smart TV with satellite channels

"Comfortably accommodated all in our party. In suite laundry was very helpful. Kitchen had all supplies needed for our stay. I would highly recommend. "

"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"

P13,582 total

includes taxes & fees

Dec 12 - Dec 13

"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...

P8,871 total

includes taxes & fees

Dec 23 - Dec 24

"Great place to stay, really clean and quiet. Beautiful space to sleep . Great aesthetic!"

P10,228 total

includes taxes & fees

Dec 23 - Dec 24

42-inch Smart TV with digital channels, TV, streaming services

"This was a great place and deserves the exceptional rating. The first night our oven didn’t work and they had it fixed first thing in the morning! All communication was quick and it had all we needed."

Free toiletries, hair dryer, towels, soap

"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"

P10,049 total

includes taxes & fees

Dec 23 - Dec 24

"Had a great time and Kosa was awesome! Staff was excellent and the communication along the way was very organized."

P6,094 total

includes taxes & fees

Dec 12 - Dec 13

"Perfect for a girls' weekend get-away. Close to CTA station and walkable to many attractions and restaurants. Comfortable and well-stocked with basic necessaries (dishes, cutlery, glassware). Added plus was the roof top terrace we enjoyed on the unseasonably balmy October evening! Our only complaint was not being able to stay longer. We hope to be back."

P7,595 total

includes taxes & fees

Dec 29 - Dec 30

"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "

P9,374 total

includes taxes & fees

Dec 23 - Dec 24

40-inch flat-screen TV with digital channels, TV

"Everything was Excellent! The property was beautiful and most of all very CLEAN!!! The way everything was set up on site , to check-in and check-out was a very seamless process. The property was also very spacious, the beds were very big in size, super comfy, and having the three bathrooms in each bedroom was a such a plus. Greek neighborhood was a wonderful and smart location, everything is walking distance: for any coffee connoisseurs: Ground up Coffee is superb, Target is only a couple blocks...

P11,887 total

includes taxes & fees

Dec 27 - Dec 28

"Overall for solo travel is recommended."

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"Was clean, service great and perfect location to walk around the city near popular attractions "

P6,894 total

includes taxes & fees

Dec 8 - Dec 9

"Convenient "

P7,452 total

includes taxes & fees

Dec 16 - Dec 17

Premium bedding, in-room safe, desk, laptop workspace

"This hotel was very clean and the staff were helpful and courteous. I would definitely stay there again. Its conveniently located near most attractions. "

P7,062 total

includes taxes & fees

Dec 11 - Dec 12

Find out more about Southwest Side

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Recent reviews of Southwest Side properties

5/5 Excellent

"Loved staying in this location. Didn’t have enough time to explore the area, but everything is accessible by walking. Will come back again when I am in town. "

A verified traveler stayed at Aloft Chicago Mag Mile

Posted 11 hours ago

5/5 Excellent

"This hotel was literally the perfect stay. It was in walkable distance of everything and we loved that the hotel was always cleaned after we walked out to our adventures. The staff were friendly and polite. The restaurant right underneath the hotel was really good we’d definitely recommend it. "

A verified traveler stayed at Eurostars Magnificent Mile

Posted 2 days ago

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Southwest Side Vacation Rentals

Check Southwest Side vacation rental availability

Vacation Rentals in Southwest Side

Sentral Michigan Avenue

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Sonder Jewelers Row

Kasa River North Chicago

Sonder The Plymouth

Sonder The Opal

Sonder Greektown

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Find out more about Southwest Side

Recent reviews of Southwest Side properties

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