Photo by Steve Luzzo

Far Southwest Side Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Vacation Rentals in Far Southwest Side

House with garage, outdoor dining and basement bar

10.0 out of 10, Exceptional, (1)
"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

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

4.0 out of 10, (3)
"There was room enough for everyone. I like the recording ring doorbell. I like bathroom connect to bedroom. I didn’t like the wide open vent in the floor leading to bathroom. The bathroom door is on backwards. The coffee pot was molded. There were plenty of towels and washcloths. The bed is too close to the wall. The neighborhood is nice and quiet. I probably would stay there again but the price was high for the condition of the house. This house needs a lot of maintenance."
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (830)
"Great stay!"
The price is CA $256
CA $341 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $256
CA $300 total
includes taxes & fees
Aug 10 - Aug 11
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 CA $292
CA $374 total
includes taxes & fees
Aug 11 - Aug 12
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 CA $290
CA $340 total
includes taxes & fees
Aug 14 - Aug 15
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 CA $314
CA $369 total
includes taxes & fees
Aug 10 - Aug 11
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 CA $237
CA $279 total
includes taxes & fees
Aug 4 - Aug 5
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 CA $221
CA $259 total
includes taxes & fees
Aug 17 - Aug 18
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. "
The price is CA $306
CA $496 total
includes taxes & fees
Aug 6 - Aug 7
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 CA $314
CA $369 total
includes taxes & fees
Aug 17 - Aug 18
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 CA $116
CA $131 total
includes taxes & fees
Jul 24 - Jul 25
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!"
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 CA $313
CA $367 total
includes taxes & fees
Aug 7 - Aug 8
Sonder by Marriott Bonvoy Greektown Apartments

Huge Projector and Designated Workspace - Near Wrigley!

The price is CA $160
CA $479 total
includes taxes & fees
Jul 24 - Jul 25
Huge Projector and Designated Workspace - Near Wrigley!

Lakeview 2BR Apartment

9.0 out of 10, Wonderful, (2)
"Great location, charming building. The photos in the listing are very accurate. Super close to the L and restaurants."
The price is CA $129
CA $256 total
includes taxes & fees
Jul 23 - Jul 24
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. "
The price is CA $129
CA $255 total
includes taxes & fees
Jul 21 - Jul 22
Clean & Equipped 1BR Apt
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.
Save an average of 15% on thousands of hotels when you're signed in