South Side holiday rentals

We found 2,315 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – South Side

Showing deals for:13 Nov - 20 Nov

Interior
Terrace/patio
Living area
Living area
Wonderful
(12 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
AU$11,773
for 7 nights, 1 apartment
AU$1,682 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Outdoors at night
River North Luxury Living
The building
Interior
Exceptional
(104 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago

7% off
AU$4,585
for 7 nights, 1 apartment
AU$655 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Living area
Interior
Room
Private kitchen
Exceptional
(8 reviews)

Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!

Chicago

7% off
AU$5,709
for 7 nights, 1 home
AU$816 per night
includes taxes & fees
Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
Dining
Interior
Living area
Private kitchen
Exceptional
(35 reviews)

Lux Home in Chicago 7mins Downtown

Chicago

7% off
AU$6,608
for 7 nights, 1 home
AU$944 per night
includes taxes & fees
Lux Home in Chicago 7mins Downtown
Interior
Interior
Private kitchen
Interior
Exceptional
(6 reviews)

EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath

Evanston

8% off
AU$12,826
for 7 nights, 1 home
AU$1,832 per night
includes taxes & fees
EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath
Living area
Room
Interior
Dining
Very good
(11 reviews)

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

Chicago

7% off
AU$2,436
for 7 nights, 1 apartment
AU$348 per night
includes taxes & fees
South Shore Chicago Condo-1 Block to Lake-WiFi-AC-Elevator-420 Friendly
Living area
Private kitchen
Room
Property grounds
Exceptional
(74 reviews)

Private Historic Coach House Wicker Park

Chicago

7% off
AU$3,373
for 7 nights, 1 home
AU$482 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Private kitchen
Living area
Living area
Dining
Exceptional
(55 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
AU$3,698
for 7 nights, 1 apartment
AU$528 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Convenient on-premis laundry room with coin operated washer and dryer
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
7 minutes drive to downtown and Millenium Park
Bedroom #1 w 2 full size beds plus a desk
Wonderful
(20 reviews)

1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
AU$2,700
for 7 nights, 1 apartment
AU$386 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Dining room area
3 bedroom unit is top floor of historic greystone
Living room area opens into dining room & kitchen
Living room area
Exceptional
(96 reviews)

Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.

Chicago

7% off
AU$6,352
for 7 nights, 1 home
AU$907 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Bedroom 1
Private kitchen
Exterior
Dining
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
AU$6,707
for 7 nights, 1 home
AU$958 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Miscellaneous
Living area
Point of interest
Room
Exceptional
(12 reviews)

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

11% off
AU$4,876
for 7 nights, 1 home
AU$697 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Room
Interior
Interior
Private kitchen
Exceptional
(10 reviews)

Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!

Chicago

7% off
AU$2,988
for 7 nights, 1 apartment
AU$427 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Private kitchen
Belmont Harbor
Living area
Exterior
Exceptional
(190 reviews)

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Chicago

14% off
AU$5,603
for 7 nights, 1 home
AU$800 per night
includes taxes & fees
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Exterior
Property grounds
Living area
Very good
(30 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
AU$1,223
for 7 nights, 1 apartment
AU$175 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
Doorman building with grand lobby
Restored grand lobby with work tables, club seating, and stained glass ceiling
Heritage Outpost cafe in lobby
Craft cocktail bar in lobby
Exceptional
(14 reviews)

Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking

Chicago

7% off
AU$2,723
for 7 nights, 1 apartment
AU$389 per night
includes taxes & fees
Newly Renovated 1 BR in Art Deco Architectural Gem, Steps to L & Free Parking
Interior
Living area
Interior
Room
Exceptional
(6 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
AU$4,466
for 7 nights, 1 apartment
AU$638 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Downstairs living room
Downstairs living area
Upstairs queen bedroom 2
Kitchen (upstairs)
Exceptional
(97 reviews)

Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

Chicago

7% off
AU$12,379
for 7 nights, 1 apartment
AU$1,768 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Exterior
Hot tub available for $50 first night..
Room
Exceptional
(106 reviews)

Lg Studio Apt. No cleaning fee. Obama Center 10 mins.

Chicago

8% off
AU$1,586
for 7 nights, 1 apartment
AU$227 per night
includes taxes & fees
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
Interior
Private kitchen
Interior
Interior
Wonderful
(49 reviews)

Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!

Chicago

8% off
AU$6,145
for 7 nights, 1 home
AU$878 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Private kitchen
Interior
Dining
Exterior
Exceptional
(13 reviews)

Spacious Duplex - 4BD/3BA - Sleeps 12!

Chicago

7% off
AU$4,748
for 7 nights, 1 apartment
AU$678 per night
includes taxes & fees
Spacious Duplex - 4BD/3BA - Sleeps 12!
Room
Exterior
Private kitchen
Dining
Exceptional
(34 reviews)

Lincoln Park Charm Near Everything + On site Parking Spot Included

Chicago

7% off
AU$8,691
for 7 nights, 1 apartment
AU$1,242 per night
includes taxes & fees
Lincoln Park Charm Near Everything + On site Parking Spot Included
Room
Living area
Interior
Dining
Exceptional
(22 reviews)

Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base

Chicago

7% off
AU$2,502
for 7 nights, 1 apartment
AU$357 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Upscale kitchen with an equally spacious dining room
5 minutes drive to McCormick Place (0.9 miles)
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
Bedroom #1 with 2 double beds and an in-suite bathroom
Wonderful
(7 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
AU$3,345
for 7 nights, 1 apartment
AU$478 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Explore the lakeside setting in South Side

Come and experience South Side and its museums, architecture and art galleries. Revered for its skyscrapers, aquarium and lake, this city is both cosmopolitan and scenic. Take in top local attractions such as McCormick Place and Lake Michigan. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around South Side

Do you want to find top things to see and do in the city? Venture out of your holiday home and experience everything that South Side has to offer. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Lincoln Park Zoo (8.1 mi / 13 km)
  • Oak Brook Golf Course (16.7 mi / 26.8 km)
  • Ravisloe Country Club (17.1 mi / 27.6 km)
  • The Dome at the Parkway Bank Sports Complex (18.3 mi / 29.4 km)
  • Cog Hill Golf & Country Club (19.9 mi / 32.1 km)
  • Orland Park Sportsplex (20.5 mi / 32.9 km)

Exploring the natural landscape of South Side

Whether you're looking for adventure or just want to appreciate the scenery, South Side is a great spot to appreciate mother nature. Here are some of the area’s most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Millennium Park (5.4 mi / 8.7 km)
  • Grant Park (4.7 mi / 7.6 km)
  • Washington Park (0.7 mi / 1.1 km)
  • Midway Plaisance (1.3 mi / 2.1 km)
  • Jackson Park (2.4 mi / 3.9 km)
  • Northerly Island (3.8 mi / 6.2 km)

Travelling to and around South Side

The nearest airport is in Chicago Midway Airport (MDW), located 6.9 mi (11.1 km) from the city centre.

If you prefer to travel by train, Chicago 47th Street Station (Kenwood), Chicago 51st-53rd Street Station (Hyde Park) and Chicago 55th-56th-57th Street Station are the main stations in the city. You can get around South Side by jumping on the metro at 51st Station, 47th Station (Green Line) or Garfield Station (Green Line).

Frequently asked questions

What is the best area to stay in South Side when booking a holiday home?
Among the more desired neighbourhoods to find a South Side holiday home is Essex. When you book your Stayz holiday property, you'll have the entire place to yourselves. So you won't have to share it with anybody other than your group.
What is the most popular type of holiday home accommodation in South Side?
Apartments are the most popular kind of holiday home in South Side, according to our data. Even if you have a different idea about what you'd like, Stayz has holiday homes in a variety of shapes and sizes. Browse our options to find your ideal fit.
How much does it cost to rent a holiday home in South Side?
Several factors affect how much you pay for a holiday home in South Side, including the type of property, length of stay and season. Still, all of our holiday homes have something in common — incredible value. Simply enter your travel dates to find your ideal match.
How much does it cost to rent a beach house in South Side?
When you travel and the style and size of the property will determine the cost of your beachside escape. Enter your South Side travel dates to view your available options on Stayz. Did someone just say "private pool"? Use our filters to select the amenities and features you need.
What are popular home amenities in South Side?
When it comes to home amenities that people look for in South Side, a microwave oven, a fridge and a dryer are at the top of the list. With Stayz holiday homes, you'll enjoy choices to fit your taste and style, whether you're taking a trip with relatives, friends or even pets.
Are there large group holiday homes in South Side?
You can pick from 14 holiday properties in South Side that can accommodate 10 or more guests. Whether you're planning a family trip or a special event, there's plenty of room to get your group together under the same roof.
What are the top attractions for families in South Side?
Keep the kids busy at these fun family-friendly attractions in South Side:
  • Jackson Park
  • Guaranteed Rate Field
  • Abbott Park
Can I find two-bedroom holiday homes in South Side?
Select from 26 two-bedroom homes in South Side. Put the kids in the second room or fill it with a couple of your best friends. There's a comfy spot for whoever's lucky enough to be joining in on the fun.
Are there holiday homes with WiFi in South Side?
South Side has 105 holiday homes with WiFi, so you can stay connected during your trip. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming TV shows with the family to catching up on social media, these Stayz homes will keep you online.
How old do you have to be to rent a holiday home in South Side?
The minimum required age is normally 16, 18 or 21. It can change between properties on Stayz, so look at the rules of your chosen South Side stay before you book.
How long can I rent a holiday home in South Side for?
The amount of time you can book a South Side holiday home for depends on each property. Simply put in your travel dates to browse available options offering longer term stays. They have all you need to make your extended holiday more enjoyable and convenient, like air conditioning and kitchens. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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