South Side holiday homes

We found 2,391 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – South Side

Showing deals for:1 Jan - 8 Jan

Interior
Our downtown Townhouse is in an amazing location
Dining
It is huge! With lots of areas for relaxing and entertaining
Exceptional
(92 reviews)

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$12,485
for 7 nights, 1 home
NZ$1,784 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
The building
River North Luxury Living
Outdoors at night
French Bistro and Wine Bar - right downstairs
Exceptional
(106 reviews)

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

Chicago

7% off
NZ$6,674
for 7 nights, 1 apartment
NZ$953 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Interior
Interior
Private kitchen
Room
Exceptional
(9 reviews)

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

Chicago

7% off
NZ$7,483
for 7 nights, 1 home
NZ$1,069 per night
includes taxes & fees
Near Lakefront! Minutes from the beach, Obama museum campus and 2 golf courses!!
Interior
Interior
Terrace/patio
Interior
Exceptional
(6 reviews)

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

Evanston

8% off
NZ$16,098
for 7 nights, 1 home
NZ$2,300 per night
includes taxes & fees
EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath
Dining
Living area
Room
Kitchen
Exceptional
(31 reviews)

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

Chicago

7% off
NZ$2,790
for 7 nights, 1 apartment
NZ$399 per night
includes taxes & fees
Sunny 2-Bedroom Logan Square Apartment – Your Perfect Chicago Base
Bedroom 3 w/ Queen Bed
Top floor kitchen and dining area
2 spots come with the unit- occupied by the van and SUV in this photo.
Dining Area
Exceptional
(34 reviews)

The Exclusive- 7 Bed, 6 Bath Retreat

Chicago

5% off
NZ$10,464
for 7 nights, 1 apartment
NZ$1,495 per night
includes taxes & fees
The Exclusive- 7 Bed, 6 Bath Retreat
Living room area
3 bedroom unit is top floor of historic greystone
View of Robey Hotel from back deck
Living room area opens into dining room & kitchen
Exceptional
(101 reviews)

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

Chicago

7% off
NZ$10,481
for 7 nights, 1 home
NZ$1,497 per night
includes taxes & fees
Wicker Park 3 Bedroom. Top floor Historic Greystone. Near Damen El Stop.
Living Room with 60 in Smart TV
Chef kitchen with Sub-Zero refrigerator, Wolf stove, Bosch dishwasher.
Bedroom 1 - King Bed
Living Room with 60 in Smart TV
Exceptional
(92 reviews)

Stunning Lincoln Park Single-Family House with Fantastic Game Room

Chicago

11% off
NZ$11,905
for 7 nights, 1 home
NZ$1,701 per night
includes taxes & fees
Stunning Lincoln Park Single-Family House with Fantastic Game Room
Interior
Room
Interior
Terrace/patio
Exceptional
(75 reviews)

Private Historic Coach House Wicker Park

Chicago

6% off
NZ$4,261
for 7 nights, 1 home
NZ$609 per night
includes taxes & fees
Private Historic Coach House Wicker Park
Room
Living area
Private kitchen
Dining
Exceptional
(114 reviews)

Wrigley Field/Lakeview -Entire Home- Large Groups!

Chicago

11% off
NZ$9,752
for 7 nights, 1 home
NZ$1,393 per night
includes taxes & fees
Wrigley Field/Lakeview -Entire Home- Large Groups!
Bedroom 1
Private kitchen
Living area
Exterior
Wonderful
(22 reviews)

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Chicago

7% off
NZ$8,135
for 7 nights, 1 home
NZ$1,162 per night
includes taxes & fees
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago
Terrace/patio
Living area
Living area
Dining
Exceptional
(57 reviews)

Cozy two bedroom close to Wrigley Field

Chicago

15% off
NZ$5,248
for 7 nights, 1 apartment
NZ$750 per night
includes taxes & fees
Cozy two bedroom close to Wrigley Field
Room
Interior
Dining
Living area
Exceptional
(38 reviews)

Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10

Chicago

7% off
NZ$10,601
for 7 nights, 1 home
NZ$1,514 per night
includes taxes & fees
Lincoln Park 3BR Townhome • Rooftop • King Suite • Sleeps 10
Fun Mirror Wall Upstairs
Downstairs living area
Downstairs living room
Kitchen (upstairs)
Exceptional
(99 reviews)

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

Chicago

7% off
NZ$17,777
for 7 nights, 1 apartment
NZ$2,540 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Interior
Private kitchen
Interior
Dining
Wonderful
(50 reviews)

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

Chicago

7% off
NZ$6,870
for 7 nights, 1 home
NZ$981 per night
includes taxes & fees
Gorgeous 5 BDR/ 4BA in Logan Square w/Parking!
Dining
Living area
Living area
Interior
Exceptional
(14 reviews)

Wicker Park: Cozy Fireplace, Grand Piano

Chicago

25% off
NZ$7,127
for 7 nights, 1 apartment
NZ$1,018 per night
includes taxes & fees
Wicker Park: Cozy Fireplace, Grand Piano
Living area
Interior
Interior
Private kitchen
Exceptional
(12 reviews)

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

Chicago

7% off
NZ$3,746
for 7 nights, 1 apartment
NZ$535 per night
includes taxes & fees
Peaceful Living-2Bdrm/2Bath w/Private Parking, WiFi-Work Station-Wicker Park!
Terrace/patio
Exterior
Interior
Dining
Exceptional
(14 reviews)

Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12

Chicago

7% off
NZ$9,461
for 7 nights, 1 apartment
NZ$1,352 per night
includes taxes & fees
Spacious 6BR South Loop Luxury Suite Near McCormick Place & Soldier Field for 12
Games room
Exterior
Living area
Private kitchen
Very good
(33 reviews)

Peaceful place Great location food markets transportation downtown lake Michigan

Chicago

7% off
NZ$1,869
for 7 nights, 1 apartment
NZ$267 per night
includes taxes & fees
Peaceful place Great location food markets transportation downtown lake Michigan
Living area
Dining
Living area
Room
Exceptional
(7 reviews)

The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.

Chicago

6% off
NZ$13,610
for 7 nights, 1 apartment
NZ$1,944 per night
includes taxes & fees
The Dakin Estate: A refined 4BR Art Deco speakeasy duplex in Wrigleyville. Featuring curated interiors, elevated finishes, and a private entertainment lounge just minutes from Wrigley Field, dining, nightlife, and Chicago’s iconic attractions.
Outdoor dining
Property grounds
Room
Exterior detail
Exceptional
(30 reviews)

2BD/1 BA with summer patio in quiet Roscoe Village

Chicago

7% off
NZ$2,608
for 7 nights, 1 apartment
NZ$373 per night
includes taxes & fees
2BD/1 BA with summer patio in quiet Roscoe Village
Interior
Rush Medical Center one of the best in the nation
Fully Equipped Kitchen
Bar (on property)
Exceptional
(373 reviews)

Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Chicago

7% off
NZ$2,630
for 7 nights, 1 apartment
NZ$376 per night
includes taxes & fees
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Room
Living area
Games room
Games room
Exceptional
(9 reviews)

Elite 4BR Art Deco suite. Garage included.

Chicago

7% off
NZ$11,061
for 7 nights, 1 apartment
NZ$1,580 per night
includes taxes & fees
Elite 4BR Art Deco suite. Garage included.
Sunny Bay Window
Polk Street
Room 2  Queen bed  black out curtains vintage snd Original art and a TV
Stop by say Hello to Dave our neighbor at his newest hipest Italian eatery
Exceptional
(314 reviews)

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago

7% off
NZ$3,477
for 7 nights, 1 apartment
NZ$497 per night
includes taxes & fees
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
  • 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:

  • Harborside International Golf Center (7.8 mi / 12.5 km)
  • Lincoln Park Zoo (8.1 mi / 13 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)
  • Seven Bridges Golf Club (24 mi / 38.7 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)
  • Jackson Park (2.4 mi / 3.9 km)
  • Northerly Island (3.8 mi / 6.2 km)
  • Burnham Park (4 mi / 6.4 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 Bookabach 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, Bookabach 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 Bookabach. 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 Bookabach 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 Bookabach 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 Bookabach, 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.

More holiday ideas