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Check prices for these dates

In two weeks
19 Sep - 21 Sep
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov
In four months
26 Dec - 28 Dec

Top Holiday Rentals in Far Southwest Side

Our top choices for Far Southwest Side holiday rentals

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (900)
"great food spots all around and beautiful sites to see "
The price is ฿4,370
฿6,079 total
includes taxes & fees
3 Sept - 4 Sept
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (490)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (346)
"A lot of good food options walkable distance. "
The price is ฿7,910
฿10,006 total
includes taxes & fees
3 Sept - 4 Sept
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (352)
"Great stay!"
The price is ฿5,465
฿6,415 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (637)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is ฿4,818
฿5,656 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (194)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (209)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is ฿6,289
฿7,383 total
includes taxes & fees
21 Sept - 22 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (336)
"Easy parking. Close to El. Nice condo."
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is ฿5,465
฿6,416 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is ฿5,141
฿6,035 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (19)
"Excellent location and very clean! Would stay again!"
The price is ฿2,675
฿4,756 total
includes taxes & fees
3 Sept - 4 Sept
Wrigleyville Suites
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (166)
"This place has everything for a multi-night stay."
Kasa River North Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | 1 bedroom, desk, laptop workspace, blackout curtains

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

3.0 star property
3.8 out of 10, (58)
"Good "
The price is ฿2,734
฿3,088 total
includes taxes & fees
4 Sept - 5 Sept
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (134)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ฿6,111
฿7,174 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Art Villa
Hot tub

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is ฿24,233
฿40,079 total
includes taxes & fees
9 Sept - 10 Sept
Art Villa
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is ฿6,839
฿8,028 total
includes taxes & fees
28 Sept - 29 Sept
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (17)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is ฿3,547
฿6,516 total
includes taxes & fees
15 Sept - 16 Sept
Ground Floor Studios in Chicago by 747 Lofts
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 Southwest Side Hotel Reviews

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

10/10 Excellent
"I enjoyed my stay here "
Carmen 1-night trip
Posted 10 days ago
The Allegro Royal Sonesta Hotel Chicago Loop

Find out more about Far Southwest Side

Find out more about Far Southwest Side

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