South Side Vacation Rentals

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Check prices for these dates

Vacation Rentals in South Side

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (680)
"This is a great hotel. The rooms have a kitchenette and the staff is wonderful! Beautiful hotel, great amenities. "
The price is P6,371
P9,184 total
includes taxes & fees
Feb 24 - Feb 25
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (432)
"Loved the app and process for checking-in and out. The property itself could use some TLC, there were lots of scuff marks and scratches in the walls due to prior tenants. Our unit could have used a painting. There also wasn't a space to get extra toiletries per the app, would take this out if it's not really an option. "
The price is P5,681
P6,669 total
includes taxes & fees
Mar 23 - Mar 24
Sonder South Wabash

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (186)
"It was a Great option, straight and contactless."
The price is P7,013
P8,233 total
includes taxes & fees
Mar 23 - Mar 24
Found Chicago powered by Sonder

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (257)
"It was wonderful!"
The price is P6,578
P7,722 total
includes taxes & fees
Mar 13 - Mar 14
Sonder Market Hall

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (140)
"My unit was very nice and more than perfect for my needs. It was spacious and quiet. There is little going on in the area in the evenings which I found a bit unnerving as an older adult. You know - there's safety in numbers! "
The price is P7,295
P8,563 total
includes taxes & fees
Mar 6 - Mar 7
Sonder The Burnham Apartments

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (363)
"Great extended stay with full kitchen and area. "
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (288)
"Amazing stay ! Love this property every time I’m in Chicago. "
The price is P8,869
P11,709 total
includes taxes & fees
Feb 24 - Feb 25
Level Chicago – Old Town

Comfort Inn Chicago Wind Creek Casino

2.5 star property
4.8 out of 10, (3)
"I was told on arrival that my room was given to somebody else I wasn’t notified or nothing and I’m still waiting on a refund"
The price is P5,462
P6,171 total
includes taxes & fees
Feb 22 - Feb 23
Comfort Inn Chicago Wind Creek Casino

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (258)
"Best place to stay in Chicago. "
Kasa South Loop Chicago

The Neighborhood Hotel-Little Italy

3.5 star property
9.8 out of 10, Exceptional, (130)
"I love it"
The Neighborhood Hotel-Little Italy

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (137)
"Loved it Had to leave early but loved "
The price is P5,968
P7,006 total
includes taxes & fees
Mar 12 - Mar 13
Sonder Jewelers Row

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (125)
"The property is very nice, we will definitely coming back soon "
The price is P5,449
P6,396 total
includes taxes & fees
Feb 26 - Feb 27
Kasa River North Chicago

Sonder The Opal

3.5 star property
8.6 out of 10, Excellent, (28)
"Our stay was amazing. "
The price is P5,639
P6,620 total
includes taxes & fees
Mar 12 - Mar 13
Sonder The Opal

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very Good, (90)
"Great apartment, we were given an extra bedroom which we used as a wardrobe. Well equipped, modern and well decorated. Full cooker, fridge freezer, microwave. We were provided with tablets for laundry and dishwasher. Washing up.liquids, towels and toilet roll. Great shower. Loved the location. We enjoy cities and walking. Trains a very short walks (several L stations). Target was a 15 minute walk, great independent coffee shop 2 mins from entrance. We will use Sonder again. "
The price is P6,689
P7,853 total
includes taxes & fees
Feb 23 - Feb 24
Sonder The Plymouth

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (40)
"I loved how easy it was to find and the instructions to access was easy to follow"
The price is P7,332
P8,607 total
includes taxes & fees
Mar 13 - Mar 14
Sonder Greektown

Wrigleyville Suites

2.0 star property
10.0 out of 10, Exceptional, (2)
The price is P8,383
P12,751 total
includes taxes & fees
Feb 21 - Feb 22
Wrigleyville Suites

Chic Chicago Retreat 2 Bedroom Home by RedAwning

3.0 star property
Chic Chicago Retreat 2 Bedroom Home by RedAwning
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

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3799)
"Biggest downsides to the property is that you are adjacent to Wacker and Michigan - both have high possibilities for noise (sirens, honking, etc) which I dealt with during my stay. Good dining options in the area, many within a 5 minute walk. Room size was fairly compact, but for a one night stay was not an issue in the slightest. Lobby was very nice as well! Staff were easy to find in the lobby to ask for help checking in, I would happily stay here again."
The price is P4,750
P5,576 total
includes taxes & fees
Mar 9 - Mar 10
River Hotel

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8525)
"A comfortable historical hotel, enjoyed the bar area, cocktails were good , would not recommend dining at the hotel. On Expedia it says it has parking and in and out privileges but this is not true, once you park you cant leave unless paying again (62$) . Had a paranormal experience in room 917 so don't be surprised if you see ghosts at night "
The price is P4,978
P5,844 total
includes taxes & fees
Feb 23 - Feb 24
Congress Plaza Hotel

L7 Chicago by LOTTE

4.5 star property
9.6 out of 10, Exceptional, (1662)
"Nice place but can be noisy."
The price is P7,509
P8,815 total
includes taxes & fees
Feb 23 - Feb 24
L7 Chicago by LOTTE
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.