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

South Side Vacation Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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, (1,299 reviews)
"A great place"
United States
Lahiru
The price is RM615
RM840 total
includes taxes & fees
8 Sept - 9 Sept
Sentral Michigan Avenue

2. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (25 reviews)
"Great location and super clean!"
United States
Erica
The price is RM752
RM1,135 total
includes taxes & fees
7 Sept - 8 Sept
Kasa Lake Shore Chicago
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, (520 reviews)
"We only stayed one night but we definitely want to go back and stay at least two nights. It really was beautiful, clean and very secure."
United States
Martha
The price is RM1,027
RM1,306 total
includes taxes & fees
7 Sept - 8 Sept
Level Chicago – Old Town
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

Carlton Inn Midway

Carlton Inn Midway

10/10 Excellent
"It’s very Good, good location, good parking, good room and good employees"
Icaro 1-night trip
Posted 7 hours ago
Carlton Inn Midway

Find out more about South Side

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