South Side Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for South Side holiday rentals

Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (12 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Modern Studio Near UChicago
TV
Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is HK$452
HK$1,384 total
includes taxes & fees
12 Jan - 13 Jan
Sleek & Functional 2-Bedroom Apt
2 bedrooms, iron/ironing board, travel cot, WiFi
Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave
Hyde Park
8.4 out of 10, Very good, (5 reviews)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
The price is HK$452
HK$1,384 total
includes taxes & fees
12 Jan - 13 Jan
Explore Hyde Park: 2BR Apt on Blackstone Ave
TV, offices
Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"
United States
christine m.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Bright 1BR Unit in a Prime Spot
Interior
Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment
Hyde Park
9.0 out of 10, Wonderful, (7 reviews)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Chic Retreat: Cozy 1BR Apartment
TV
Bright South Hyde Park Studio

Bright South Hyde Park Studio

Bright South Hyde Park Studio
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"Comfortable space in a nice neighborhood. I highly recommend."
United States
BiggDas M.
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Bright South Hyde Park Studio
Iron/ironing board, travel cot, WiFi, bed sheets
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location was just perfect!"
United States
Meg D.
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Studio Unit | Chic + Prime Location
1 bedroom, iron/ironing board, travel cot, WiFi
Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark
Hyde Park
8.4 out of 10, Very good, (15 reviews)
"The location couldn't be beat. The beds were super comfortable and the room was perfect for my husband and I. We'll definitely stay here again!"
United States
Lisa O.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Modern 1BR in Historic HydePark
Iron/ironing board, travel cot, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$444
HK$1,180 total
includes taxes & fees
14 Jan - 15 Jan
Cozy Charm Studio Apt in Chicago
Iron/ironing board, travel cot, WiFi, bed sheets
Compact Studio for a Relaxed Stay

Compact Studio for a Relaxed Stay

Compact Studio for a Relaxed Stay
Hyde Park
8.0 out of 10, Very good, (1 review)
The price is HK$444
HK$1,180 total
includes taxes & fees
13 Jan - 14 Jan
Compact Studio for a Relaxed Stay
Iron/ironing board, travel cot, WiFi, bed sheets
Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago

Trendy Studio Apartment in Chicago
Hyde Park
8.0 out of 10, Very good, (3 reviews)
"Loved my two-night stay here. The apartment was spotless, quiet, and in the perfect location for my UChicago visit. Check-in info arrived a bit later than expected, but communication overall was thoughtful and helpful, and everything worked out smoothly. Would happily stay again."
United States
Helmut P.
The price is HK$444
HK$1,180 total
includes taxes & fees
14 Jan - 15 Jan
Trendy Studio Apartment in Chicago
1 bedroom, iron/ironing board, WiFi, bed sheets
Charming 1BR/1BA Apt in Chicago

Charming 1BR/1BA Apt in Chicago

Charming 1BR/1BA Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (1 review)
The price is HK$491
HK$1,313 total
includes taxes & fees
25 Jan - 26 Jan
Charming 1BR/1BA Apt in Chicago
TV, offices
Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions

Perfect 1BR Spot near Attractions
Hyde Park
7.8 out of 10, Good, (6 reviews)
"We were there visiting our daughter at Hyde Park. The location was great, near restaurants and shopping. The space was comfortable and clean. "
United States
Alex & Minerva B.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Perfect 1BR Spot near Attractions
3 bedrooms, iron/ironing board, WiFi, bed sheets
Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry

Furnished 3BR Apt w/ Laundry
Hyde Park
9.6 out of 10, Exceptional, (5 reviews)
"Apartment and neighborhood were beautiful. We really enjoyed our stay and would book the same place again!"
United States
Kristin W.
The price is HK$585
HK$1,657 total
includes taxes & fees
15 Jan - 16 Jan
Furnished 3BR Apt w/ Laundry
Iron/ironing board, travel cot, WiFi, bed sheets
Cozy Well-Equipped Studio Apt

Cozy Well-Equipped Studio Apt

Cozy Well-Equipped Studio Apt
Hyde Park
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Cozy Well-Equipped Studio Apt
TV
Contemporary 2BR Apartment in Vibrant Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
The price is HK$452
HK$1,384 total
includes taxes & fees
12 Jan - 13 Jan
Contemporary 2BR Apartment in Vibrant Hyde Park
WiFi, bed sheets
Trendy Studio in Vibrant Area

Trendy Studio in Vibrant Area

Trendy Studio in Vibrant Area
Hyde Park
The price is HK$444
HK$1,180 total
includes taxes & fees
12 Jan - 13 Jan
Trendy Studio in Vibrant Area
2 bedrooms, iron/ironing board, travel cot, WiFi
Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location

Bright & Spacious 2BR– Prime Hyde Park Location
Hyde Park
7.0 out of 10, Good, (2 reviews)
"Great stay! The owners were easy to communicate with and were accompanying! The property was clean and close to stores, restaurants, and shops! Would stay again in the future! "
United States
Jeremy M.
The price is HK$452
HK$1,423 total
includes taxes & fees
12 Jan - 13 Jan
Bright & Spacious 2BR– Prime Hyde Park Location
Fridge, microwave, oven, stovetop
3BR | Complete & Well-Located

3BR | Complete & Well-Located

3BR | Complete & Well-Located
Hyde Park
7.6 out of 10, Good, (5 reviews)
"Very nice place! Not many kitchen amenities available as there was no way to heat up something in the oven with no baking sheet or foil. Getting into the apartment was not very easy as we had to call a number to be remotely let in every time we wanted to use the front door."
United States
Teri D.
The price is HK$585
HK$1,657 total
includes taxes & fees
12 Jan - 13 Jan
3BR | Complete & Well-Located
1 bedroom, desk, iron/ironing board, travel cot
Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago

Bright & Cozy 1BR Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (3 reviews)
"This apartment is a very basic rental unit – – had what we needed for our three nights stay, and we were very pleased. Great value for the money."
United States
Alan F.
The price is HK$491
HK$1,313 total
includes taxes & fees
12 Jan - 13 Jan
Bright & Cozy 1BR Near UChicago
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

SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown

10/10 Excellent
"Very easy, friendly staff"
William 1-night trip
Posted 9 hours ago
SpringHill Suites by Marriott Chicago Chinatown

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