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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, (1,347 reviews)
"Nice room, will stay again, highly recommend:)"
United States
Reina
The price is NT$5,590
NT$7,498 total
includes taxes & fees
Oct 26 - Oct 27
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (49 reviews)
"Location is perfect"
United States
Mary
The price is NT$5,862
NT$8,862 total
includes taxes & fees
Nov 1 - Nov 2
Kasa Lake Shore Chicago
A modern kitchen with a large island, bar stools, and a city view.

3. 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 NT$8,091
NT$10,283 total
includes taxes & fees
Nov 1 - Nov 2
Level Chicago – Old Town
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, (274 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is NT$6,140
NT$7,029 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 NT$7,397
NT$12,006 total
includes taxes & fees
Oct 7 - Oct 8
At Home in Oak Park
A building with a white exterior and a tree with white blossoms in front.

6. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is NT$7,672
NT$12,325 total
includes taxes & fees
Oct 21 - Oct 22
Historic Oak Park Residence
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

10/10 Excellent
"Hotel was very clean, grateful housekeeping came in everyday and provided clean towels. Room view was very nice and as advertised."
Erica 4-night trip
Posted 5 hours ago
The Royal Sonesta Chicago Downtown

Find out more about Southwest Side

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