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Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Southwest Side vacation rentals

A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (93 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is P9,680
P15,294 total
includes taxes & fees
Nov 22 - Nov 23
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

2. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is P7,571
P8,887 total
includes taxes & fees
Nov 17 - Nov 18
Wrigleyville Suites
A high-rise building with a glass facade, surrounded by other buildings.

3. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
"Great for extended stays."
United States
Jeff
The price is P12,176
P14,294 total
includes taxes & fees
Dec 15 - Dec 16
Sentral Michigan Avenue
A high-rise building with multiple floors, large windows, and a modern architectural design.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is P10,840
P14,297 total
includes taxes & fees
Nov 23 - Nov 24
Level Chicago – Old Town
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 Southwest Side Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"Very much enjoyed our stay. Staff was amazing!! Breakfast was excellent."
Frances 3-night trip
Posted 3 hours ago
Fairmont Chicago at Millennium Park

Find out more about Southwest Side

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Look no further and take a look at our great range of rental properties in Southwest Side!