Southwest Side Vacation Rentals

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Vacation Rentals in Southwest Side

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (822)
"Great stay!"
$220 nightly
The price is $258
Aug 4 - Aug 5
Total includes taxes and fees
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."
$186 nightly
The price is $219
Aug 10 - Aug 11
Total includes taxes and fees
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (326)
"Hotel was nice"
$261 nightly
The price is $306
Aug 11 - Aug 12
Total includes taxes and fees
Level Chicago – Old Town

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (443)
"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, (566)
"Great place and location. "
$212 nightly
The price is $248
Aug 14 - Aug 15
Total includes taxes and fees
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, (194)
"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. "
$229 nightly
The price is $268
Aug 10 - Aug 11
Total includes taxes and fees
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."
$131 nightly
The price is $154
Aug 4 - Aug 5
Total includes taxes and fees
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (72)
"Good people great breakfast "
$232 nightly
The price is $266
Jul 16 - Jul 17
Total includes taxes and fees
The Gem Museum Suites

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (173)
"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, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
$161 nightly
The price is $189
Aug 10 - Aug 11
Total includes taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (155)
"Great location and very clean! Will definitely be staying again. "
$284 nightly
The price is $334
Jul 21 - Jul 22
Total includes taxes and fees
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. "
$214 nightly
The price is $251
Aug 10 - Aug 11
Total includes taxes and fees
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. "
$87 nightly
The price is $99
Jul 16 - Jul 17
Total includes taxes and fees
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!"
$128 nightly
The price is $142
Jul 16 - Jul 17
Total includes taxes and fees
Wrigleyville Suites

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
$219 nightly
The price is $257
Aug 10 - Aug 11
Total includes taxes and fees
Sonder by Marriott Bonvoy Greektown Apartments

Huge Projector and Designated Workspace - Near Wrigley!

Huge Projector and Designated Workspace - Near Wrigley!

Lakeview 2BR Apartment

10.0 out of 10, Exceptional, (1)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
$208 nightly
The price is $211
Jul 28 - Jul 29
Total includes taxes and fees
Lakeview 2BR Apartment

Clean & Equipped 1BR Apt

10.0 out of 10, Exceptional, (1)
"Was very clean and comfortable simply furnished but nice close to the things we were looking for. "
$184 nightly
The price is $186
Jul 20 - Jul 21
Total includes taxes and fees
Clean & Equipped 1BR Apt

Cozy, Fully Set-Up 1BR Space

10.0 out of 10, Exceptional, (2)
"Great communication, location, and would love to stay here again "
$184 nightly
The price is $186
Jul 16 - Jul 17
Total includes taxes and fees
Cozy, Fully Set-Up 1BR Space
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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