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Search Holiday Rentals in Far Southwest Side

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Top Holiday Rentals in Far Southwest Side

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (831)
"Great stay!"
The price is ฿6,048
฿8,053 total
includes taxes & fees
17 Aug - 18 Aug
Sentral Michigan Avenue

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (323)
"Super cool spot in a great part of the city."
The price is ฿6,044
฿7,095 total
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (328)
"Hotel was nice"
The price is ฿15,210
฿18,580 total
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (444)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (572)
"Great place and location. "
The price is ฿6,766
฿7,942 total
includes taxes & fees
14 Aug - 15 Aug
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (318)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (196)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is ฿7,428
฿8,720 total
includes taxes & fees
10 Aug - 11 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.0 out of 10, Very good, (117)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ฿5,630
฿6,609 total
includes taxes & fees
4 Aug - 5 Aug
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (176)
"Great spot. "
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (169)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is ฿5,219
฿6,127 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (156)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (42)
"Our stay was amazing. "
The price is ฿7,428
฿8,720 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Opal Apartments River North

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

2.5 star property
3.6 out of 10, (47)
"the property is under renovation it should not be open. There were no amenities, i.e., ice. The room was clean. "
The price is ฿2,747
฿3,103 total
includes taxes & fees
31 Jul - 1 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
The price is ฿4,792
฿7,249 total
includes taxes & fees
20 Jul - 21 Jul
Wrigleyville Suites

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is ฿7,148
฿8,391 total
includes taxes & fees
7 Aug - 8 Aug
Sonder by Marriott Bonvoy Greektown Apartments
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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