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Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Southwest Side vacation rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,346 reviews)
"Great venue"
United States
Arthur Noel
The price is P10,958
P14,699 total
includes taxes & fees
Oct 26 - Oct 27
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

2. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (532 reviews)
"Location and facility was very nice"
United States
Brian
The price is P17,784
P22,420 total
includes taxes & fees
Sep 30 - Oct 1
Level Chicago – Old Town
Lake

3. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (48 reviews)
"Location is perfect"
United States
Mary
The price is P14,323
P20,746 total
includes taxes & fees
Oct 1 - Oct 2
Kasa Lake Shore Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (272 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is P11,164
P12,781 total
includes taxes & fees
Oct 29 - Oct 30
The Gem Museum Suites
Terrace/patio

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is P13,933
P22,895 total
includes taxes & fees
Oct 6 - Oct 7
At Home in Oak Park
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

6. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.2 out of 10, Wonderful, (7 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The price is P11,108
P19,661 total
includes taxes & fees
Oct 13 - Oct 14
The Oak Park Loft
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

River Hotel

River Hotel

8/10 Good
"The rooms were clean and beds were comfortable. The staff were very helpful and friendly"
Richard 2-night trip
Posted less than an hour ago
River Hotel

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!