A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for South 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, (1,366 reviews)
"Perfect location to stay at if attending the bears games !"
United States
Jacob
The price is ฿5,231
฿6,140 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Lake

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (63 reviews)
"Location is perfect"
United States
Mary
The price is ฿6,002
฿9,129 total
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A modern living room with a grey sectional sofa, a round coffee table, and a glass desk with a chair. Large windows offer a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (540 reviews)
"Great location, very clean, loved the gym and cafe!"
United States
Kerry
The price is ฿9,293
฿11,736 total
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

4. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (283 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is ฿8,450
฿9,673 total
includes taxes & fees
9 Nov - 10 Nov
The Gem Museum Suites
Terrace/patio

5. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, Exceptional, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is ฿6,427
฿11,081 total
includes taxes & fees
25 Oct - 26 Oct
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.

6. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
7.6 out of 10, Good, (63 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is ฿5,251
฿6,164 total
includes taxes & fees
3 Nov - 4 Nov
Wrigleyville Suites
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. 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 ฿5,405
฿9,910 total
includes taxes & fees
27 Oct - 28 Oct
Historic Oak Park Home
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 ฿8,114
฿15,921 total
includes taxes & fees
14 Oct - 15 Oct
Classic Forest Park Foursquare < 1 Mi to Blue Line
A modern building with large glass windows, surrounded by a grassy area with trees and a pathway.

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 price is ฿3,648
฿7,900 total
includes taxes & fees
28 Oct - 29 Oct
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 South Side Hotel Reviews

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

10/10 Excellent
"Jill at the desk is the best! She goes above and beyond for guests, so kind and helpful."
Michael 2-night trip
Posted 8 hours ago
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Find out more about South Side

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Look no further and take a look at our great range of rental properties in South Side!