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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Far Southeast Side holiday rentals

A waterfront promenade with high-rise buildings, a sandy beach, and a pedestrian walkway.

1. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (84 reviews)
"The bathroom was really clean. The beds were really comfortable"
United States
Jair
The price is Rp2.748.464
Rp4.342.534 total
includes taxes & fees
22 Nov - 23 Nov
Kasa Lake Shore Chicago
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,405 reviews)
"10/10 2nd time staying here!"
United States
Rosa
The price is Rp2.300.030
Rp2.700.004 total
includes taxes & fees
7 Dec - 8 Dec
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (558 reviews)
"Super clean and friendly staff! Would definitely stay here again"
United States
Robert Edward
The price is Rp3.075.820
Rp4.056.788 total
includes taxes & fees
23 Nov - 24 Nov
Level Chicago – Old Town
A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

4. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (49 reviews)
"Clean room"
United States
Michael
The price is Rp2.685.177
Rp3.152.128 total
includes taxes & fees
9 Nov - 10 Nov
Wrigleyville Suites
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

5. 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 Rp4.375.844
Rp8.585.876 total
includes taxes & fees
9 Nov - 10 Nov
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 Far Southeast Side Hotel Reviews

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.
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 Southeast Side

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