Holiday Rentals in South Side

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Holiday Rentals in South Side

3BR Prime Hyde Park Location Near University of Chicago and Dining

2.0 star property
10.0 out of 10, Exceptional, (5)
"Excellent stay in a good location. The place is comfortable and big, the host was very kind and attentive. I hope to comeback soon. ☺️"
3BR Prime Hyde Park Location Near University of Chicago and Dining

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (13)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

House with garage, outdoor dining and basement bar

10.0 out of 10, Exceptional, (1)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

Newly Revamped Home - For privacy lovers

10.0 out of 10, Exceptional, (1)
"it was amazing and spacious. it was the perfect home for adults to visit and enjoy themselves."
Newly Revamped Home - For privacy lovers

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (831)
"Great stay!"
The price is €213
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (323)
"Super cool spot in a great part of the city."
The price is €188
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (328)
"Hotel was nice"
The price is €492
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (444)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (572)
"Great place and location. "
The price is €210
includes taxes & fees
14 Aug - 15 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (318)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (196)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is €231
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (117)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is €175
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Gem Museum Suites

3.5 star property
9.6 out of 10, Exceptional, (76)
"Good people great breakfast "
The price is €234
includes taxes & fees
6 Aug - 7 Aug
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (176)
"Great spot. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is €162
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is €231
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (48)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is €82
includes taxes & fees
1 Aug - 2 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is €170
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites
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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Top South Side Hotel Reviews