Search Holiday Rentals in Far Southwest Side
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Our top choices for Far Southwest Side holiday rentals

Aparthotel in Downtown Chicago
Sentral Michigan Avenue9.2 out of 10, Wonderful, (1020)
The price is 3.111.231 ₫
4.425.022 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026

Aparthotel in Downtown Chicago
Chicago luxury home suites8.4 out of 10, Very good, (5)
The price is 3.552.660 ₫
4.170.468 ₫ total
includes taxes & fees
28 Dec - 29 Dec

Aparthotel in Downtown Chicago
Level Chicago – Old Town9.0 out of 10, Wonderful, (405)

Aparthotel in Downtown Chicago
Kasa River North Chicago9.6 out of 10, Exceptional, (182)

ENVITAE Hotel 4 Bedroom Luxury Apartments
ENVITAE Hotel 4 Bedroom Luxury Apartments10.0 out of 10, Exceptional, (8)
The price is 9.260.600 ₫
16.400.750 ₫ total
includes taxes & fees
30 Dec - 31 Dec
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.
Top Far Southwest Side Hotel Reviews

Embassy Suites by Hilton Chicago Downtown River North
10/10 Excellent
























