Photo by Steve Luzzo

Far Southwest Side Vacation Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Far Southwest Side

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"We stayed stayed at the Sentral for a business/family trip. This hotel is beautiful and accommodating. Sandra at the front desk was the sweetest and made check in a breeze, even allowing us to check in early. The room was clean, however there was a burn mark on the kitchen floor and it appeared as it was not vacuumed. Otherwise the room was wonderful, we would definitely stay here again! "
The price is P6,350
P9,183 total
includes taxes & fees
Nov 25 - Nov 26
Sentral Michigan Avenue
Sonder Market Hall
Interior

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is P3,307
P3,882 total
includes taxes & fees
Dec 22 - Dec 23
Sonder Market Hall
Sonder South Wabash
Living area

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"This property was in a good location - walked to Shedd Aquarium, Soldier Field, and good restaurants on South Michigan. Asked a few questions via text with prompt responses. No complaints with this clean property exactly as advertised."
The price is P7,104
P8,339 total
includes taxes & fees
Dec 19 - Dec 20
Sonder South Wabash
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, (332)
"Fantastic location with great proximity to shopping, restaurants, and sights. Well equipped, clean, spacious rooms, "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
50-inch Smart TV with satellite channels

The Neighborhood Hotel-Little Italy

3.5 star property
9.6 out of 10, Exceptional, (101)
"Excellent place to stay! "
The Neighborhood Hotel-Little Italy
Level Chicago – Old Town
Front of property - evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (269)
"Beautiful place with amazing amenities. Perfect stay for adults or families alike! Highly recommend!"
The price is P10,341
P13,141 total
includes taxes & fees
Nov 24 - Nov 25
Level Chicago – Old Town
Found Chicago powered by Sonder
Exterior

Found Chicago powered by Sonder

3.5 star property
7.6 out of 10, Good, (176)
"Excellent location, amazing price. No nonsense stay, you only get the basics here but very clean and simple. Pros: no carpet in rooms, no extra frilly pillows or curtains, all surfaces look like they can be easily wiped down and disinfected. You can actually open the windows. Self serve toiletry station. Coded locks instead of keys. Great location close to restaurants and bus stops. THE PRICE!!! Cons: non responsive staff in person and online, sometimes no staff at all. No view, stuffy room...
The price is P6,835
P8,023 total
includes taxes & fees
Dec 17 - Dec 18
Found Chicago powered by Sonder
Sonder The Burnham Apartments
Marina

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (114)
"The room is really cute and has all the amenities (including washing machine and dishwasher). Staying for business though I could hear quite a lot of noise from other rooms which made sleeping difficult at night "
The price is P8,185
P9,609 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Burnham Apartments
Kasa South Loop Chicago
42-inch Smart TV with digital channels, TV, streaming services

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (233)
"Amazing stay!"
Kasa South Loop Chicago
Sonder Jewelers Row
Free toiletries, hair dryer, towels, soap

Sonder Jewelers Row

3.5 star property
8.2 out of 10, Very Good, (132)
"I so enjoyed staying on jewelers row at the Sonder property In Chicago. It was very close to the places I was visiting so I could walk everywhere. It was noisy because of the L train, yes, but when you’re inside, you Barely hear the train. I felt very safe getting into the building and getting up to my room. It was so well appointed. You thought of everything! I just wish I had longer than three days in Chicago and I hope to come back. I would rent the same apartment again without a doubt!"
The price is P8,014
P9,408 total
includes taxes & fees
Dec 23 - Dec 24
Sonder Jewelers Row
Kasa River North Chicago
Exterior

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (100)
"First pick for my first trip to Chicago. I felt safe and I was able to walk to the diner, mall and restaurants. Highly recommend this place!"
The price is P5,111
P6,000 total
includes taxes & fees
Dec 8 - Dec 9
Kasa River North Chicago
Sonder The Plymouth
City view from property

Sonder The Plymouth

3.5 star property
8.2 out of 10, Very Good, (83)
"Perfect for a girls' weekend get-away. Close to CTA station and walkable to many attractions and restaurants. Comfortable and well-stocked with basic necessaries (dishes, cutlery, glassware). Added plus was the roof top terrace we enjoyed on the unseasonably balmy October evening! Our only complaint was not being able to stay longer. We hope to be back."
The price is P6,585
P7,731 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Plymouth
Sonder The Opal
Exterior

Sonder The Opal

3.5 star property
8.4 out of 10, Very Good, (25)
"Stayed here twice - great place to stay when visiting. Easily walkable to shops, attractions and dining! "
The price is P7,495
P8,798 total
includes taxes & fees
Dec 23 - Dec 24
Sonder The Opal
Sonder Greektown
40-inch flat-screen TV with digital channels, TV

Sonder Greektown

3.5 star property
9.0 out of 10, Wonderful, (33)
"The place was awesome, they had to kick out the people before me, so getting my room was a little bit late "
The price is P9,327
P10,949 total
includes taxes & fees
Dec 17 - Dec 18
Sonder Greektown
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.8 out of 10, Exceptional, (11)
"Overall for solo travel is recommended."
Ground Floor Studios in Chicago by 747 Lofts
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.
Don't see what you're looking for?
See all available properties in Far Southwest Side
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Far Southwest Side you may be interested in

Congress Plaza Hotel
Lobby

Congress Plaza Hotel

3.5 star property
7.8 out of 10, Good, (8199)
"Our stay was great! Easy check in, room and all areas were clean and smelled wonderful! "
The price is P7,592
P8,912 total
includes taxes & fees
Dec 4 - Dec 5
Congress Plaza Hotel
River Hotel
View from property

River Hotel

4.0 star property
8.8 out of 10, Excellent, (3569)
"I loved the view from my room! I loved that it is right in the middle of Downtown!!! I would stay here again."
The price is P5,876
P6,897 total
includes taxes & fees
Dec 23 - Dec 24
River Hotel
Club Quarters Hotel, Central Loop, Chicago
Premium bedding, in-room safe, desk, laptop workspace

Club Quarters Hotel, Central Loop, Chicago

4.0 star property
8.6 out of 10, Excellent, (3292)
"This is a go-to hotel for me near a yearly event I participate in. It's the best value of any of the hotels in its immediate surrounding area."
The price is P5,660
P6,645 total
includes taxes & fees
Dec 23 - Dec 24
Club Quarters Hotel, Central Loop, Chicago
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.