Photo by by Midway Intl Airport

South Side Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Interior
Chic Retreat: Cozy 1BR Apartment

Chic Retreat: Cozy 1BR Apartment

Hyde Park
9.0 out of 10, Wonderful, (6)
"Our stay was very nice, with simple checkin / check out, and excellent communication by our host. "
United States
Tom B.
The price is ￥8,554
￥24,746 total
includes taxes & fees
Nov 30 - Dec 1
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 ￥9,332
￥24,101 total
includes taxes & fees
Dec 1 - Dec 2
Modern Studio Near UChicago
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is ￥37,695
￥60,292 total
includes taxes & fees
Dec 8 - Dec 9
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"Everything was perfect with the property and the host even came to help right away when we had one issue with the lights."
United States
Isaiah P.
LakeHouse
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, (25)
"Perfect for what we needed"
United States
Richard G.
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Dining
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Hyde Park
10.0 out of 10, Exceptional, (2)
"Location was just perfect!"
United States
Meg D.
The price is ￥9,332
￥24,101 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
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)
"We liked that the condo was very clean and felt like home."
United States
Sherry
1-bedroom condo next to Chicago Midway International Airport
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!
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 ￥9,332
￥24,101 total
includes taxes & fees
Dec 1 - Dec 2
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)
"I thought this place was so cute, loved the outset deck! Was spacious and the host was very nice and helpful when needed! Would stay again for sure! "
United States
Jaime C.
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, (15)
"Our group of 16 people really enjoyed staying at this property. We were so close to everything, surrounded by great food amd shopping, we felt very safe, and the property manager was so responsive to us! We would recommended this property to any family or big group and will be staying here if we come back to Chicago!"
United States
Lindsey M.
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, (2)
"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
Exterior
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions

Bronzeville
8.4 out of 10, Very Good, (11)
"We found the place to be extremly clean and comfortable . Its really close to down town and great resturants. Definetly would book again ."
United States
sean r.
Bright 2 Bed/2 Bath Condo With Patio Less Than 10 Mins From Major Attractions
Microwave, oven, stovetop, dishwasher
Stay, Relax & Explore Chicago

Stay, Relax & Explore Chicago

Greater Grand Crossing
9.4 out of 10, Exceptional, (3)
"I lovedddd my stay !"
United States
antoniah s.
Stay, Relax & Explore Chicago
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
2 bedrooms, iron/ironing board, free WiFi, bed sheets
Stay near family or close to downtown, this loft in Beverly has it all!

Stay near family or close to downtown, this loft in Beverly has it all!

Beverly
9.8 out of 10, Exceptional, (11)
"We really enjoyed our time in Chicago for our family reunion. The price was spot on as the hotels cost in Chicago are super expensive. The location was very safe, great area for restaurants and shopping. We will definitely stay here again. Also, great host! "
United States
Theresa S.
Stay near family or close to downtown, this loft in Beverly has it all!
Game room
Urban Family one block away from the lake and golf course.

Urban Family one block away from the lake and golf course.

South Shore
6.0 out of 10, (2)
"Never received check in information, had to call from multiple phones to receive answer. Found dirty shorts underneath bed, doors don’t close, boarded up window, exposed screws on the couch - my friend cut their foot on the screw. Overall was not worth the price based on the above and more that was not stated. Would not recommend. "
United States
Jadyn
Urban Family one block away from the lake and golf course.
Fridge, microwave, oven, stovetop
Come experience The Lake Shore!

Come experience The Lake Shore!

South Shore
10.0 out of 10, Exceptional, (4)
"Very spacious, quiet and comfortable. Great place to stay!"
United States
Kylie M.
Come experience The Lake Shore!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 4 days ago
Motel 6 - Chicago, IL

Find out more about South Side

Search for holiday rentals in South Side on Expedia! You can easily find your home rentals, villas, holiday apartments in South Side using one of the methods below:

  • View our selection of featured holiday rentals in South Side
  • Use the map to find apartments and other holiday homes in the South Side neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in South Side while they last

Look no further and take a look at our great range of rental properties in South Side!