South Side Vacation Rentals

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Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in South Side

Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (10)
"Good communication and easy check-in"
United States
Chen
The price is ￥10,046
￥24,855 total
includes taxes & fees
Dec 3 - Dec 4
Cozy Studio in Hyde Park-Walk to Lake & University
Interior
Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment

Hyde Park
9.0 out of 10, Wonderful, (6)
"Very quiet and comfortable. Right in the heart of Hyde Park. 10 min walk to Lake Michigan.Clean and well suited for your needs. Would gladly stay again!"
United States
Harold M.
The price is ￥9,891
￥26,219 total
includes taxes & fees
Dec 3 - Dec 4
Chic Retreat: Cozy 1BR Apartment
Iron/ironing board, travel crib, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Hyde Park
9.4 out of 10, Exceptional, (9)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥10,046
￥24,855 total
includes taxes & fees
Dec 3 - Dec 4
Modern Studio Near UChicago
1 bedroom, iron/ironing board, travel crib, WiFi
Modern 1BR in Historic HydePark

Modern 1BR in Historic HydePark

Hyde Park
7.8 out of 10, Good, (10)
"Comfortable space. All the necessary amenities. Extremely walkable to everything.Will stay again. "
United States
jasmine h.
The price is ￥10,046
￥26,400 total
includes taxes & fees
Dec 3 - Dec 4
Modern 1BR in Historic HydePark
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is ￥36,396
￥58,691 total
includes taxes & fees
Nov 17 - Nov 18
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (23)
"Nice place, everything clean, the only downside is parking"
United States
quy u.
LakeHouse
Fridge, microwave, oven, stovetop
Explore Hyde Park: 2BR Apt on Blackstone Ave

Explore Hyde Park: 2BR Apt on Blackstone Ave

Hyde Park
9.4 out of 10, Exceptional, (3)
"All the necessities with no personal touches. Keys from lockbox to open second door were not needed as the second door is always open. Impeccable communication with host. Great location, close to restaurants and train to Millennium Station. Coffee service was excellent, just be sure to find extra pouches in cabinet. Bathtub faucet could not be turned far enough to prevent leaking. TV remote not great and I couldn’t get CNN or MSNBC. I’d stay here again. "
United States
lost whale press
The price is ￥12,982
￥32,540 total
includes taxes & fees
Dec 3 - Dec 4
Explore Hyde Park: 2BR Apt on Blackstone Ave
Beach
The Chic Urban Oasis Near the Lake!

The Chic Urban Oasis Near the Lake!

South Shore
8.0 out of 10, Very Good, (7)
"Great property in not the best part of town. "
United States
Scott S.
The Chic Urban Oasis Near the Lake!
Dining
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (1)
"Unit was convenient to our son’s home. Comfortable home. All the necessities were provided. "
United States
Michelle F.
The price is ￥9,273
￥23,949 total
includes taxes & fees
Dec 1 - Dec 2
Studio Unit | Chic + Prime Location
Smart TV
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Bronzeville
9.6 out of 10, Exceptional, (74)
"Enough room for a quick get away"
United States
wendy C.
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
Smart TV
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

Bronzeville
10.0 out of 10, Exceptional, (24)
"Nice property conveniently located. Easy to get to UChicago campus and downtown. We were in town for UChicago graduation and this place was a good balance for various celebratory activities.Everyone loved the massage chair! Good sized bedrooms and bathrooms. "
United States
Tamara J.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Fridge, microwave, oven, stovetop
1-bedroom condo next to Chicago Midway International Airport

1-bedroom condo next to Chicago Midway International Airport

Garfield Ridge
10.0 out of 10, Exceptional, (11)
"Everything was clean and as advertised. The only comment is that the shower was warm at best and not hot"
United States
Simeon
1-bedroom condo next to Chicago Midway International Airport
1 bedroom, WiFi
Toca Bella ~ 7mins to Downtown

Toca Bella ~ 7mins to Downtown

Bronzeville
9.8 out of 10, Exceptional, (19)
"Enjoyed my stay. "
United States
Thomas M.
Toca Bella ~ 7mins to Downtown
Fridge, microwave, oven, stovetop
Lux Home in Chicago 7mins Downtown

Lux Home in Chicago 7mins Downtown

Bronzeville
9.8 out of 10, Exceptional, (28)
"Larry was super responsive, the property was spotless, the location perfect. Our group of friends loved it. We will be back! "
United States
Kyle B.
Lux Home in Chicago 7mins Downtown
Iron/ironing board, travel crib, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago

Hyde Park
10.0 out of 10, Exceptional, (1)
The price is ￥9,582
￥24,312 total
includes taxes & fees
Dec 3 - Dec 4
Cozy Charm Studio Apt in Chicago
Fridge, microwave, oven, stovetop
Modern Condo-Obama & University of Chicago Area

Modern Condo-Obama & University of Chicago Area

Woodlawn
8.6 out of 10, Excellent, (14)
"It's not often that I'm a complainer. But I have to say, we were appalled by the rental. First and foremost the locks on both front glass doors have been bashed out so anyone can get in. They don't even latch. We never had to open the lockbox, we just walked right in.We had to spend time attempting to get the tops of the windows to close. Ultimately we couldn't force them all closed. It was the biggest problem on friday and Saturday nights when we faced honking cars, fighting tenants, amd very...
United States
Michele V.
Modern Condo-Obama & University of Chicago Area
Fridge, microwave, oven, stovetop
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chinatown
10.0 out of 10, Exceptional, (14)
"We totally enjoyed our stay in the condo. Very spacious and clean. We felt very safe with our family there. Parking was a little hard but lots of things to do within walking distance."
United States
Anonymous traveler
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Fridge, microwave, oven, dishwasher
House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar

Auburn Gresham
8.8 out of 10, Excellent, (6)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
United States
Jessica M.
House with garage, outdoor dining and basement bar
Dining
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly

South Chicago
10.0 out of 10, Exceptional, (1)
"Clean apartment and great communication with host. Fixed any small problems very quickly. "
United States
Catherine F.
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Microwave, oven, stovetop, dishwasher
Stay, Relax & Explore Chicago

Stay, Relax & Explore Chicago

Greater Grand Crossing
9.4 out of 10, Exceptional, (3)
"Our stay was a pleasant surprise. The house was newly renovated and even nicer than the online pictures. Our host Demarcus was quick to respond to our questions and needs. We will stay there again when we go back to visit my granddaughter, a student at UI C "
United States
Maria A.
Stay, Relax & Explore Chicago
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

Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center

10/10 Excellent
"The staff is always courteous, helpful, professional, and genuinely nice. I am there on a weekly basis and always feel welcomed. I appreciate how they value my business. Most importantly I love that their eyes smile like their happy to help."
Chequrita 1-night trip
Posted 2 days ago
Hyatt Place Chicago-South/University Medical Center

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