South Side Vacation Rentals

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Check prices for these dates

In two weeks
Dec 5 - Dec 7
In two months
Jan 16 - Jan 18
In three months
Feb 13 - Feb 15
In four months
Mar 13 - Mar 15

Vacation Rentals in South Side

Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is P14,673
P23,311 total
includes taxes & fees
Dec 1 - Dec 2
Stylish Apartment near Chicago Downtown
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P6,977
P9,924 total
includes taxes & fees
Dec 7 - Dec 8
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.4 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is P4,571
P5,366 total
includes taxes & fees
Nov 19 - Nov 20
Wrigleyville Suites
Floor plan
Spacious 3BR Home Firepit & Grill

Spacious 3BR Home Firepit & Grill

2.0 star property
Miller Beach
The price is P9,154
P24,779 total
includes taxes & fees
Dec 1 - Dec 2
Spacious 3BR Home Firepit & Grill
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is P17,717
P20,797 total
includes taxes & fees
Nov 19 - Nov 20
Chicago luxury home suites
Private kitchen
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"Overall solid property, I will return."
United States
Fletcher
The price is P3,738
P8,236 total
includes taxes & fees
Nov 30 - Dec 1
River West, Third Floor Chicago by 747 Lofts
Private kitchen
The Gem Museum Suites

The Gem Museum Suites

3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (96)
"Great stay. The studio is small but has everything necessary."
United States
Julia
The price is P10,713
P12,264 total
includes taxes & fees
Dec 15 - Dec 16
The Gem Museum Suites
Exterior
Historic Oak Park Residence

Historic Oak Park Residence

2.0 star property
Oak Park
9.6 out of 10, Exceptional, (12)
"Absolutely awesome "
United States
Erik
The price is P9,133
P17,014 total
includes taxes & fees
Nov 20 - Nov 21
Historic Oak Park Residence
Free WiFi
Logan Square SRO Hotel

Logan Square SRO Hotel

2.0 star property
Logan Square
The price is P10,607
P16,871 total
includes taxes & fees
Nov 24 - Nov 25
Logan Square SRO Hotel
Interior
Walk to Wrigley Field! Townhouse w/ Pool Table

Walk to Wrigley Field! Townhouse w/ Pool Table

3.0 star property
Lakeview
The price is P12,728
P35,359 total
includes taxes & fees
Dec 1 - Dec 2
Walk to Wrigley Field! Townhouse w/ Pool Table
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is P16,286
P38,893 total
includes taxes & fees
Dec 18 - Dec 19
Art Villa
Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

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

3.0 star property
Harvey
3.8 out of 10, (67)
"Good "
United States
Abel
The price is P4,282
P4,838 total
includes taxes & fees
Dec 2 - Dec 3
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Front of property
Spacious 3BR House With Firepit & Grill, Near Beach

Spacious 3BR House With Firepit & Grill, Near Beach

2.0 star property
Miller Beach
5.0 out of 10, (2)
"It is a beautiful residence. This is a relatively new residence, evidenced by all the brand new with tags furniture, lamps, appliances etc. No internet or cable, which was sort of a downer. Did not get the code until 15 minutes after check in time. No coffee or silverware. We only found one spoon. "
United States
Kaitlyn
The price is P8,876
P21,516 total
includes taxes & fees
Dec 17 - Dec 18
Spacious 3BR House With Firepit & Grill, Near Beach
Exterior
River West, Second Floor Chicago by 747 Lofts

River West, Second Floor Chicago by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (4)
"I need to somewhere to stay for a night in Chicago and found this place. It had a varying level of reviews but found the property more the suitable for what I paid. Easy to follow instructions to get in, clean, and convienent. They even provide ear plugs to drown out the sounds of the city."
United States
Anonymous traveler
The price is P3,909
P13,443 total
includes taxes & fees
Nov 20 - Nov 21
River West, Second Floor Chicago by 747 Lofts
Exterior
Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts

2.0 star property
West Town
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is P3,439
P12,833 total
includes taxes & fees
Nov 30 - Dec 1
Chicago Third Floor Studio by 747 Lofts
Private kitchen
Chicago Second Floor Studio by 747 Lofts

Chicago Second Floor Studio by 747 Lofts

2.0 star property
West Town
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is P3,432
P7,819 total
includes taxes & fees
Dec 1 - Dec 2
Chicago Second Floor Studio by 747 Lofts
Interior
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 P10,253
P22,697 total
includes taxes & fees
Nov 19 - Nov 20
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 South Side Hotel Reviews

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

10/10 Excellent
"Antonio is so great and handsome "
Rashka Sade 1-night trip
Posted 2 days ago
Motel 6 - Chicago, IL

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