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Far Southwest Side Vacation Rentals

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Vacation 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, (951)
"Great location and cleanliness of rooms. Staff was extremely helpful "
The price is ¥29,958
¥39,496 total
includes taxes & fees
Oct 7 - Oct 8
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (548)
"Very great place to stay!"
The price is ¥21,500
¥33,895 total
includes taxes & fees
Oct 7 - Oct 8
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (362)
"Great place to stay. Loved it!"
Level Chicago – Old Town

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (375)
"Great stay!"
The price is ¥18,677
¥21,925 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (235)
"Great location and lovely amenities. "
The price is ¥21,184
¥24,868 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (357)
"nice area, shops nearby"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (677)
"great room, clean good space and close to places "
The price is ¥22,438
¥26,340 total
includes taxes & fees
Oct 22 - Oct 23
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (207)
"This place was perfect "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (53)
"Place was in a great location close to good restaurants "
The price is ¥22,438
¥26,340 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy The Opal Apartments River North

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (170)
"This place has everything for a multi-night stay."
Kasa River North Chicago

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is ¥9,358
¥18,361 total
includes taxes & fees
Oct 7 - Oct 8
Wrigleyville Suites

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (181)
"Great location!!!"
The price is ¥21,184
¥24,868 total
includes taxes & fees
Nov 2 - Nov 3
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

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

3.0 star property
3.8 out of 10, (62)
"Good "
The price is ¥10,717
¥12,108 total
includes taxes & fees
Oct 7 - Oct 8
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Stylish Apartment near Chicago Downtown

2.0 star property
The price is ¥28,614
¥50,036 total
includes taxes & fees
Oct 7 - Oct 8
Stylish Apartment near Chicago Downtown

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.6 out of 10, Good, (140)
"Very clean and affordable "
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Clean & Equipped 1BR Apt

9.4 out of 10, Exceptional, (26)
"Good experience. Would stay there again "
The price is ¥11,503
¥27,437 total
includes taxes & fees
Nov 3 - Nov 4
Clean & Equipped 1BR Apt

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is ¥38,987
¥94,839 total
includes taxes & fees
Oct 13 - Oct 14
Art Villa

Charming 2BR in Vibrant Lakeview

9.4 out of 10, Exceptional, (19)
"This place was great! Loved my stay!"
The price is ¥12,977
¥31,375 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2BR in Vibrant Lakeview

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
The price is ¥13,567
¥29,855 total
includes taxes & fees
Oct 8 - Oct 9
Stylish 1BR in West Loop
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

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Find out more about Far Southwest Side

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