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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (1,391 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is ₹12,860
₹15,096 total
includes taxes & fees
22 Nov - 23 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, (76 reviews)
"Amazing property would stay here again. Looks exactly like pics!!"
United States
Felipe
The price is ₹13,170
₹21,312 total
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
9.4 out of 10, Exceptional, (48 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 ₹14,125
₹16,582 total
includes taxes & fees
29 Oct - 30 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, (551 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is ₹16,887
₹22,171 total
includes taxes & fees
9 Nov - 10 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, (295 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ₹19,024
₹21,778 total
includes taxes & fees
3 Nov - 4 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
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 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 ₹23,019
₹45,165 total
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

River Hotel

River Hotel

8/10 Good
"Cool old building with a beautiful lobby (retro). Room was skinny, but so is the building. AC was loud in room, but worked well. Bed was ok, but had a big dip in it on one side. Room was very clean and housekeeping cleaned each day, unlike many hotels that do not. View was nice of river, but window was small (older building). Overall, it wasn't worth the cost because there's cheaper hotels that are newer, with larger rooms and more amenities."
Michael 2-night trip
Posted 1 hour ago
River Hotel

Find out more about Southwest Side

Holiday Rentals in Southwest Side

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