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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Far Southwest Side holiday rentals

A high-rise building with a glass facade, surrounded by other buildings.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,415 reviews)
"Great for extended stays."
United States
Jeff
The price is Rp3.453.454
Rp4.054.010 total
includes taxes & fees
6 Dec - 7 Dec
Sentral Michigan Avenue
A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (90 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is Rp2.745.424
Rp4.167.134 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A high-rise building with multiple floors, large windows, and a modern architectural design.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (563 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is Rp3.121.114
Rp4.109.467 total
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A two-story house with a brick exterior, a sloped roof, and a front porch.

4. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (14 reviews)
"Great location with parking included"
United States
Melissa
At Home in Oak Park
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

5. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (51 reviews)
"The area was nice! Many restaurants and stores are at walking distance Room was very nice and clean"
United States
Francisco
The price is Rp2.145.766
Rp2.518.914 total
includes taxes & fees
30 Nov - 1 Dec
Wrigleyville Suites
A two-story house with a prominent evergreen tree in front, surrounded by various shrubs and a driveway.

6. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
8.8 out of 10, Excellent, (6 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is Rp3.887.516
Rp6.465.763 total
includes taxes & fees
16 Nov - 17 Nov
Historic Oak Park Home
A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

7. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is Rp4.371.004
Rp8.576.379 total
includes taxes & fees
16 Nov - 17 Nov
Classic Forest Park Foursquare < 1 Mi to Blue Line
A residential street with a well-maintained garden, a large coniferous tree, and a house in the background.

8. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
Historic Oak Park Residence
A large brick building with a prominent entrance, a wheelchair accessibility sign, and a pedestrian crossing sign.

9. The Oak Park Loft

The Oak Park Loft
2.0 star property
Oak Park
9.4 out of 10, Exceptional, (8 reviews)
"Good location, nice neighborhood, restaurants close"
United States
Linda
The Oak Park Loft
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

A hotel entrance with a prominent 'MORTON' sign, a 'HOTEL BLAKE CHICAGO' sign, and a '542' address number.
Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago

Hilton Vacation Club Hotel Blake Chicago
Downtown Chicago

10/10 Excellent

Great location from both airports. Lovely hotel clean and convenient
United Kingdom
Kanokkan
Reviewed October 31, 2026
Hilton Vacation Club Hotel Blake Chicago

Find out more about Far Southwest Side

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