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Southwest Side Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Southwest Side holiday rentals

A modern building with the name 'SENIORAL' prominently displayed on the facade.

1. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,387 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is S$215
includes taxes & fees
9 Nov - 10 Nov
Sentral Michigan Avenue
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (74 reviews)
"First time staying there and we absolutely loved our stay. We will definitely be going back."
United States
Iliana
The price is S$309
includes taxes & fees
4 Nov - 5 Nov
Kasa Lake Shore Chicago
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

3. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.0 out of 10, Wonderful, (49 reviews)
"What a gem right next to Wrigleyville Stadium! I had an emergency and needed somewhere to stay for two nights while my son was in the hospital. This was the perfect accommodation walkable to where I needed to go. Clean community townhome with lock off rooms, community kitchen and living room room – very lovely environment and excellent location. Walkable to many restaurants."
United States
Diana
The price is S$223
includes taxes & fees
25 Oct - 26 Oct
Wrigleyville Suites
A modern kitchen with a large island, bar stools, and a city view.

4. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (548 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is S$451
includes taxes & fees
2 Nov - 3 Nov
Level Chicago – Old Town
A spacious lobby with a high ceiling, a reception desk, comfortable seating, and a large stained glass window.

5. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (292 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is S$292
includes taxes & fees
6 Nov - 7 Nov
The Gem Museum Suites
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

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 S$404
includes taxes & fees
27 Oct - 28 Oct
Historic Oak Park Home
A large brick house with a central chimney, a covered porch, and a brick pathway leading to the entrance.

7. 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 price is S$401
includes taxes & fees
27 Oct - 28 Oct
The Oak Park Loft
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. 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 S$606
includes taxes & fees
29 Oct - 30 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
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 Southwest Side Hotel Reviews

L7 Chicago by LOTTE

L7 Chicago by LOTTE

10/10 Excellent
"Great location and very nice room"
Dimitri 1-night trip
Posted less than an hour ago
L7 Chicago by LOTTE

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