Search Holiday Rentals in Far Southwest Side
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Far Southwest Side holiday rentals
Aparthotel in Downtown Chicago
Sentral Michigan Avenue9.2 out of 10, Wonderful, (1020)
"This place made a great landing spot for a holiday weekend w family. Clean, great location, loved the holiday decorations and indoor pool / outside hot tub. Will stay again! "
Deidre
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)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Alex
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)
"Great location, clean room and friendly staff!"
Scott
Aparthotel in Downtown Chicago
Kasa River North Chicago9.6 out of 10, Exceptional, (182)
"Awesome stay "
Sally
ENVITAE Hotel 4 Bedroom Luxury Apartments
ENVITAE Hotel 4 Bedroom Luxury Apartments10.0 out of 10, Exceptional, (8)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
Javeria
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
