Vacation Rentals in South Shore, IL

Modern Chicago Condo about 9 Miles to Downtown!
7.7

Very good

·
South Shore
·
4 br
·
Sleeps 8
·
Hot Tub · Air Conditioning · Furnished ·
From
$238/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Hot Tub
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Modern Chicago Condo ~ 9 Miles to Downtown!
6

Good

·
South Shore
·
4 br
·
Sleeps 8
·
Ceiling Fan · Toiletries · Walk In Closets ·
From
$115/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Ceiling Fan
Toiletries
Walk In Closets
Tv
Microwave
Air Conditioning
Oven
Wifi
Other spaces
Kitchen
Beautiful home with Arcade and Movie Theater for you and your family to enjoy.
9

Excellent

·
South Shore
·
3 br
·
Sleeps 10
·
Hot Tub · Smoking Allowed · Air Conditioning ·
From
$264/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Hot Tub
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Spacious two bedroom condo with a cozy feel!

No reviews

·
South Shore
·
2 br
·
In Unit Laundry · Furnished · Wifi ·
From
$178/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
In Unit Laundry
Furnished
Wifi
NEW! Spacious Chicago Home w/ Deck & Fire Pit!

No reviews

·
South Shore
·
4 br
·
Sleeps 8
·
Fireplace · Central Heat · Outdoor Space ·
From
$225/night
Check availability
Property
House · 4 Beds · 4 baths
Amenities
Fireplace
Central Heat
Ceiling Fan
Toiletries
Walk In Closets
Tv
Microwave
Oven
Other spaces
Balcony, Kitchen
BEAUTIFUL 4/20 FRIENDLY 2 BEDROOM DUPLEX IN SIZZLING SOUTH SHORE

No reviews

·
South Shore
·
2 br
·
Sleeps 6
·
Beach · Lake · Waterfront ·
From
$179/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Beach
Lake
Waterfront
Fitness Center
Hardwood Floor
Dishwasher
Smoking Allowed
Air Conditioning
Other spaces
Kitchen
A luxury vintage condo close to lakefront and minutes from downtown!

No reviews

·
South Shore
·
2 br
·
Hardwood Floor · Dishwasher · Air Conditioning ·
From
$296/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Hardwood Floor
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Oasis on the lake
10

Excellent

·
South Shore
·
3 br
·
Sleeps 16
·
On Site Laundry · Workspace · Balcony ·
From
$286/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
On Site Laundry
Dishwasher
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Workspace, Balcony, Kitchen

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
Modern Condo
9

Excellent

·
South Shore
·
4 br
·
Sleeps 10
·
High Ceilings · Outdoor Space · Fitness Center ·
From
$411/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
High Ceilings
Fitness Center
Dishwasher
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Oven
Other spaces
Workspace, Balcony, Kitchen
Massive 4 Bedroom 3 Bath Condo 2 blocks from Beach

No reviews

·
South Shore
·
4 br
·
Sleeps 12
·
Free Parking · Hardwood Floor · Air Conditioning ·
From
$646/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Free Parking
Hardwood Floor
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Showing 1 - 10 of 10 results
Expand your search criteria to see more vacation rentals near South Shore.

Explore more stays nearby

Get the Woodlawn Experience! Steps away from UofC and Chicago's Lakefront.
10

Excellent

·
Woodlawn
·
3 br
·
Outdoor Space · Workspace · Air Conditioning ·
From
$253/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Workspace, Kitchen
NEW! Cozy Chicago Condo: Close to Parks & Downtown

No reviews

·
Woodlawn
·
3 br
·
Central Heat · Ceiling Fan · Dishwasher ·
From
$314/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Central Heat
Ceiling Fan
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Located Near Hospitals,, Grant Park and Museums

No reviews

·
Woodlawn
·
3 br
·
Fitness Center · Air Conditioning · Furnished ·
From
$190/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Fitness Center
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
University of Chicago Luxury Two Bedroom Condo

No reviews

·
Woodlawn
·
2 br
·
Free Parking · Fitness Center · Air Conditioning ·
From
$262/night
Check availability
Property
Condo · 2 Beds · 1 bath
Amenities
Free Parking
Fitness Center
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Wheelchair Accessible
Other spaces
Kitchen
Modern 3 bedroom loft University Of Chicago
9.3

Excellent

·
Woodlawn
·
3 br
·
In Unit Laundry · Furnished · Kitchen ·
From
$323/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
In Unit Laundry
Furnished
Wifi
Other spaces
Kitchen
NEW! Charming Chicago Apartment

No reviews

·
Chatham
·
4 br
·
Central Heat · Ceiling Fan · Dishwasher ·
From
$374/night
Check availability
Property
Apartment · 4 Beds · 2 baths
Amenities
Central Heat
Ceiling Fan
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
2 bedrooms with an extra King bedroom available for extra $

No reviews

·
Woodlawn
·
3 br
·
Outdoor Space · Workspace · Dishwasher ·
From
$272/night
Check availability
Property
House · 3 Beds · 3 baths
Amenities
Dishwasher
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Residents Lounge
Other spaces
Workspace, Kitchen
Stylish Condo

No reviews

·
Woodlawn
·
2 br
·
On Site Laundry · In Unit Laundry · Furnished ·
From
$200/night
Check availability
Property
Condo · 2 Beds · 2 baths
Amenities
On Site Laundry
In Unit Laundry
Furnished
Wifi

The best of Zumper, delivered

Be the first to hear about new listings matching your search.

Email
By clicking submit, I accept Zumper's Terms and Conditions, Privacy Policy, and Community Values.
Luxury 3x2 unit minutes to the University Of Chicago & Lake Shore Drive

No reviews

·
Woodlawn
·
3 br
·
Beach · Lake · Waterfront ·
From
$200/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Beach
Lake
Waterfront
Free Parking
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Chic 3b/2.5bath duplex in the heart of Woodlawn

No reviews

·
Woodlawn
·
3 br
·
Dishwasher · Air Conditioning · Furnished ·
From
$362/night
Check availability
Property
Apartment · 3 Beds · 3 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Stylish | Modern Design | Windy City Retreat

No reviews

·
Woodlawn
·
3 br
·
Sleeps 4
·
Fireplace · Workspace · Dishwasher ·
From
$135/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
Fireplace
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Workspace, Kitchen
LONG STAY,4BED,UC 2MI,FREE PRKG,DWTN 15MIN
9.5

Excellent

·
Grand Crossing
·
8 br
·
Sleeps 8
·
Lake · Waterfront · Walk In Closets ·
From
$169/night
Check availability
Property
Apartment · 8 Beds · 1 bath
Amenities
Lake
Waterfront
Walk In Closets
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Workspace, Kitchen
Large ultra modern 3BR/1BA near Univ of Chicago
9.8

Excellent

·
Woodlawn
·
3 br
·
Sleeps 10
·
On Site Laundry · Beach · Lake ·
From
$216/night
Check availability
Property
Apartment · 3 Beds · 1 bath
Amenities
On Site Laundry
Beach
Lake
Waterfront
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
LONG STAY, 4 bd, Free Park, DWTN 15min, UofC 3 mls
10

Excellent

·
Grand Crossing
·
4 br
·
High Ceilings · Walk In Closets · Air Conditioning ·
From
$196/night
Check availability
Property
Condo · 4 Beds · 1 bath
Amenities
High Ceilings
Walk In Closets
Air Conditioning
Furnished
In Unit Laundry
Oven
Wifi
Other spaces
Kitchen
Home > Illinois Vacation Rentals > Chicago Vacation Rentals > South Shore Vacation Rentals
Updated: March 19, 2023

Learn about vacation rentals in

South Shore

Browse 10 vacation rentals near South Shore in Chicago, Illinois. If you’re interested in touring around Chicago, and you want to stay in the South Shore neighborhood, use our interactive map to find your next rental. You can see pictures of South Shore vacation rentals, view amenities and features, browse by property types, and more. Whether you’re looking for a South Shore staycation, weekend getaway, or a long vacation, we’ve got you covered. The lowest vacation rental price in South Shore is $115 per night and goes up to as much as $646 per night. Use the date filters at the top to select your travel dates and view availability.
8 of the vacation rentals near South Shore are apartments or condos. The average bathroom count for this property type is 2. The median price for these vacation units is $251 per night. There are currently 4 vacation units under this price. 2 of the vacation rentals near South Shore are houses. The average bathroom count for a vacation house near South Shore is 4. The average price for vacation houses near South Shore is $256 per night. There are 1 vacation homes under this price. The most common amenities for vacation rentals near South Shore are: furnished, wifi, and kitchen. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

2 bed rentals

3 available

3 bed rentals

2 available

4+ bed rentals

5 available

Getting around South Shore

Walking

7/10
Grab your reusable bags–many shops and stores are within walking distance.

Car

7/10
This area is close to freeways and has adequate parking options.

Transit

8/10
Popular public transit options are just a short walk from this location.

Points of interest in South Shore

Groceries

8/10
At least one grocery store within a 15-minute walk

Shopping

5/10
Variety of shops within walking distance

Cafes

3/10
Few or no cafés within walking distance

Restaurants

5/10
Some restaurants within walking distance

Parks

9/10
Large amount of park space nearby

Nightlife

2/10
Few or no bars within walking distance

Vacation Rentals in South Shore, IL FAQ

How many vacation rentals in South Shore are available?

There are currently 10 vacation rentals in South Shore available. Choose from nightly rentals, monthly rentals, weekend rentals, and weekly rentals to find your perfect stay in South Shore.

What types of vacation rental properties are available in South Shore, IL?

As of March 19, 2023, there are 2 vacation houses for rent in South Shore and 8 vacation condos and apartments for rent in South Shore, IL. Check each listing to view photos and get more details about pricing and available amenities.

Are there any vacation rentals in South Shore, IL with more than 1 bedroom?

Yes, there are 10 South Shore vacation rentals with more than 1 bedroom. To view a more detailed amenity list, click on the available properties on Vacations by Zumper.

How many pet friendly South Shore vacation rentals are available?

As of March 19, 2023, there are 1 pet friendly vacation rentals in South Shore, Illinois available. For more information about pet policies regarding dogs and cats, view the property listing or contact the leasing agent.

City Vacation Rentals In Illinois

Vacation Rentals Zion, IL