South Side Holiday Rentals

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Holiday Rentals in South Side

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

9.8 out of 10, Exceptional, (66)
"Rented with Valane for the marathon weekend. It was clean, quiet, away from the hustle of the city. It was super easy to navigate to expo, start lines, and sites. Loved jot beong couped up in a hotel room for the weekend Highly recommend Thank you so much for the great stay"
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

cozy home in Bridgeport Chicago. walking to park and river front

10.0 out of 10, Exceptional, (4)
"Good location easy communication"
cozy home in Bridgeport Chicago. walking to park and river front

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"Staff is friendly and very helpful!"
The price is AU$241
includes taxes & fees
11 Dec - 12 Dec
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is AU$125
includes taxes & fees
22 Dec - 23 Dec
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is AU$220
includes taxes & fees
19 Dec - 20 Dec
Sonder South Wabash

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (332)
"Excellent stay. Excellent location. "
Kasa Magnificent Mile Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is AU$334
includes taxes & fees
8 Dec - 9 Dec
Level Chicago – Old Town

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"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...
The price is AU$211
includes taxes & fees
19 Dec - 20 Dec
Found Chicago powered by Sonder

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"Great place to stay, really clean and quiet. Beautiful space to sleep . Great aesthetic!"
The price is AU$271
includes taxes & fees
16 Dec - 17 Dec
Sonder The Burnham Apartments

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"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."
Kasa South Loop Chicago

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very good, (132)
"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!"
The price is AU$237
includes taxes & fees
16 Dec - 17 Dec
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is AU$154
includes taxes & fees
12 Dec - 13 Dec
Kasa River North Chicago

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very good, (83)
"Our stay was pleasant and the 3 rooms and 3 bathrooms were perfect for five people."
The price is AU$252
includes taxes & fees
23 Dec - 24 Dec
Sonder The Plymouth

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Walking distance to restaurants, shops and Lake Michigan,

9.6 out of 10, Exceptional, (173)
"Good location clean"
Walking distance to restaurants, shops and Lake Michigan,

Sonder The Opal

3.5 star property
8.4 out of 10, Very good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is AU$226
includes taxes & fees
16 Dec - 17 Dec
Sonder The Opal

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

10.0 out of 10, Exceptional, (212)
"Excited about our trip to Chicago and was not disappointed. Communication was very good from the homeowner location is perfect we had a fantastic time would recommend this for anyone wanting to enjoy downtown Chicago"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in South Side you may be interested in

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8351)
"Clean updated room with great view of lake "
The price is AU$182
includes taxes & fees
8 Dec - 9 Dec
Congress Plaza Hotel

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3619)
"Hotel was beautiful "
The price is AU$196
includes taxes & fees
11 Dec - 12 Dec
River Hotel

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3393)
"The staff are very accommodating in allowing for early luggage drop off before check in and after checking out. Super convenient to local transit and Amtrak Chicago Union Station."
The price is AU$186
includes taxes & fees
11 Dec - 12 Dec
Club Quarters Hotel, Central Loop, Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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