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Southwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (1,372 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ₩192,425
₩225,887 total
includes taxes & fees
Nov 9 - Nov 10
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (68 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is ₩240,334
₩365,547 total
includes taxes & fees
Nov 2 - Nov 3
Kasa Lake Shore Chicago
Terrace/patio

3. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (13 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ₩257,346
₩443,719 total
includes taxes & fees
Oct 29 - Oct 30
At Home in Oak Park
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

4. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is ₩240,469
₩424,372 total
includes taxes & fees
Oct 27 - Oct 28
Historic Oak Park Home
A modern kitchen with a large island, bar stools, and a city view.

5. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (541 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ₩376,210
₩474,774 total
includes taxes & fees
Nov 3 - Nov 4
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

8/10 Good
"Room was good … but there was really bad sewer smell in bathroom"
Gurpreet 3-night trip
Posted 2 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Southwest Side

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