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Far Southwest Side Vacation Rentals

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Check prices for these dates

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Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
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Nov 21 - Nov 23
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Dec 19 - Dec 21

Vacation Rentals in Far Southwest Side

Our top choices for Far Southwest Side vacation rentals

Sentral Michigan Avenue
Indoor pool

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (925)
"The staff was extremely helpful and the rooms are clean with a beautiful view of downtown and the lake. I will definitely stay here again. "
The price is P10,135
P13,572 total
includes taxes & fees
Sep 24 - Sep 25
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (528)
"Very great place to stay!"
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (355)
"Real nice place 5 stars ill be back."
Level Chicago – Old Town
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.6 out of 10, Excellent, (660)
"Dangerous area at times… but not always bad. And a quick walk to the safe areas for sure!!! I would definitely stay here again."
The price is P9,650
P11,328 total
includes taxes & fees
Oct 6 - Oct 7
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.0 out of 10, Very Good, (363)
"Great stay!"
The price is P7,710
P9,051 total
includes taxes & fees
Oct 19 - Oct 20
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Kasa South Loop Chicago
Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (352)
"It was a really nice and secure property. "
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
8.8 out of 10, Excellent, (229)
"Great location and lovely amenities. "
The price is P8,968
P10,528 total
includes taxes & fees
Sep 25 - Sep 26
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (202)
"This place was perfect "
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very Good, (49)
"Place was in a great location close to good restaurants "
The price is P9,650
P11,328 total
includes taxes & fees
Oct 19 - Oct 20
Sonder by Marriott Bonvoy The Opal Apartments River North
Kasa River North Chicago
Business center

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (169)
"This place has everything for a multi-night stay."
Kasa River North Chicago
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (19)
"Excellent location and very clean! Would stay again!"
The price is P4,421
P8,046 total
includes taxes & fees
Sep 24 - Sep 25
Wrigleyville Suites
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Desk, laptop workspace, blackout drapes, free WiFi

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

3.0 star property
3.8 out of 10, (61)
"Good "
The price is P4,826
P5,453 total
includes taxes & fees
Sep 25 - Sep 26
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (180)
"Great location!!!"
The price is P10,212
P11,988 total
includes taxes & fees
Oct 1 - Oct 2
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (138)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P8,438
P9,905 total
includes taxes & fees
Oct 21 - Oct 22
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
Art Villa
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (18)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is P3,613
P7,963 total
includes taxes & fees
Sep 30 - Oct 1
Ground Floor Studios in Chicago by 747 Lofts
Sonder by Marriott Bonvoy Greektown Apartments
Living room

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (63)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is P10,796
P12,674 total
includes taxes & fees
Sep 28 - Sep 29
Sonder by Marriott Bonvoy Greektown Apartments
Stylish Apartment near Chicago Downtown
Private kitchen

Stylish Apartment near Chicago Downtown

2.0 star property
The price is P7,369
P14,552 total
includes taxes & fees
Sep 24 - Sep 25
Stylish Apartment near Chicago Downtown
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

Freehand Chicago

Freehand Chicago

10/10 Excellent
"The hotel was beautiful and unique, and the staff were friendly! We enjoyed the cocktail lounge on the first floor. My only complaint is that our Air Conditioning unit didn’t work, but we also didn’t bring that to the attention of the front desk because we had reservations somewhere and weren’t back until late, so I can’t really complain!"
Katie 1-night trip
Posted 13 hours ago
Freehand Chicago

Find out more about Far Southwest Side

Find out more about Far Southwest Side

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