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Top Holiday Rentals in Far Southwest Side

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"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

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (889)
"great food spots all around and beautiful sites to see "
The price is £146
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (478)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (347)
"Great stay!"
The price is £112
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (342)
"A lot of good food options walkable distance. "
Level Chicago – Old Town

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (191)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (626)
"Nice view, and walkable area."
The price is £112
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (207)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is £129
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (176)
"Great location!!!"
The price is £138
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (18)
"Excellent location and very clean! Would stay again!"
The price is £110
includes taxes & fees
24 Aug - 25 Aug
Wrigleyville Suites

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is £129
includes taxes & fees
24 Aug - 25 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

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

2.5 star property
3.8 out of 10, (52)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is £71
includes taxes & fees
25 Aug - 26 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (164)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (131)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is £138
includes taxes & fees
25 Aug - 26 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Charming 2BR in Vibrant Lakeview

9.0 out of 10, Wonderful, (11)
The price is £171
includes taxes & fees
3 Sept - 4 Sept
Charming 2BR in Vibrant Lakeview

Clean & Equipped 1BR Apt

8.4 out of 10, Very good, (15)
"Good experience. Would stay there again "
The price is £153
includes taxes & fees
1 Sept - 2 Sept
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

9.0 out of 10, Wonderful, (16)
"Great place! 15 min walk to Wrigley "
The price is £153
includes taxes & fees
2 Sept - 3 Sept
Cozy, Fully Set-Up 1BR Space

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is £630
includes taxes & fees
25 Aug - 26 Aug
Art Villa

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is £146
includes taxes & fees
3 Sept - 4 Sept
Cozy Studio in Hyde Park-Walk to Lake & University
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 Far Southwest Side Hotel Reviews