Near South Side holiday homes

We found 1,407 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Near South Side that are perfect for your trip. Holiday rentals provide the amenities that you need and want for you and your friends, family or even pets, such as cable TV and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Near South Side

Showing deals for:27 Nov - 4 Dec

Living area
Terrace/patio
Private kitchen
Interior
Exceptional
(13 reviews)

6BD/5BTH + Roofdeck - Downtown Chicago!

Chicago

8% off
NZ$14,419
for 7 nights, 1 apartment
NZ$2,060 per night
includes taxes & fees
6BD/5BTH + Roofdeck - Downtown Chicago!
Miscellaneous
Living area
Point of interest
Room
Exceptional
(14 reviews)

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

Chicago

11% off
NZ$5,915
for 7 nights, 1 home
NZ$845 per night
includes taxes & fees
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown
Downstairs living room
Downstairs living area
Kitchen (upstairs)
Upstairs queen bedroom 2
Exceptional
(98 reviews)

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

Chicago

7% off
NZ$16,281
for 7 nights, 1 apartment
NZ$2,326 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Living area
Exterior
Room
Hot tub available for $50 first night..
Exceptional
(106 reviews)

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

Chicago

8% off
NZ$1,827
for 7 nights, 1 apartment
NZ$261 per night
includes taxes & fees
Lg Studio Apt. No cleaning fee. Obama Center 10 mins.
Private kitchen
Living area
Interior
Room
Exceptional
(6 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
NZ$5,418
for 7 nights, 1 apartment
NZ$774 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Private kitchen
Spacious Living Room with Roku TV, sofa bed, smart thermostat, etc
Bedroom #1 w 2 full size beds plus a desk
7 minutes drive to downtown and Millenium Park
Wonderful
(24 reviews)

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

Chicago

7% off
NZ$3,185
for 7 nights, 1 apartment
NZ$455 per night
includes taxes & fees
1 #12 - 2 Bedroom / 1 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Interior
Private kitchen
Private kitchen
Room
Exceptional
(8 reviews)

Chic 1-bedroom apartment,15mims from downtown

Chicago

7% off
NZ$1,980
for 7 nights, 1 apartment
NZ$283 per night
includes taxes & fees
Chic 1-bedroom apartment,15mims from downtown
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
5 minutes drive to McCormick Place (0.9 miles)
Upscale kitchen with an equally spacious dining room
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
NZ$3,979
for 7 nights, 1 apartment
NZ$568 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Exterior
Living area
Living area
Private kitchen
Exceptional
(14 reviews)

Cozy apartment near zoo, DePaul, Oz Park and much more!

Chicago

7% off
NZ$5,302
for 7 nights, 1 apartment
NZ$757 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!
Private kitchen
Living area
Room
Dining
Wonderful
(8 reviews)

Great Location. 5min to McCormick place. Downtown. Chinatown

Chicago

7% off
NZ$3,485
for 7 nights, 1 apartment
NZ$498 per night
includes taxes & fees
Great Location. 5min to McCormick place. Downtown. Chinatown
Interior
Property grounds
Room
Interior
Exceptional
(6 reviews)

3bed/1 bath Retreat - 10 min from Downtown

Chicago

8% off
NZ$3,613
for 7 nights, 1 apartment
NZ$516 per night
includes taxes & fees
3bed/1 bath Retreat - 10 min from Downtown
Bedroom #4 with a double and single bed
Living area
Interior
Well stocked kitchen with Keurig coffee maker, microwave, water filter and more
Exceptional
(19 reviews)

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

Chicago

7% off
NZ$6,092
for 7 nights, 1 apartment
NZ$870 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Interior
Exterior
Room
Private kitchen
Wonderful
(15 reviews)

1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Chicago

7% off
NZ$5,935
for 7 nights, 1 apartment
NZ$848 per night
includes taxes & fees
1 #31 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

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    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday home accommodation in Near South Side?
Apartments are the most popular style of holiday home in Near South Side, according to our data. Even if you have something different in mind, Bookabach has properties in a variety of shapes and sizes. Look over our options to find your ideal fit.
How much does it cost to rent a holiday home in Near South Side?
Length of stay, season and property type are some of the conditions that can influence the price of a holiday home. Simply enter your dates of travel to find your dream escape. From cosy country cottages to expansive luxury villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Near South Side?
The average price for a holiday home close to the beach in Near South Side depends on when you're visiting the area and the style and size of property you want. Find prices quickly and easily on Bookabach by entering your preferred travel dates. Then use the filters to select the number of bedrooms and amenities that you prefer, such as WiFi, air conditioning and a hot tub.
Are there pet-friendly holiday homes in Near South Side?
Yes. There are. You'll have your pick of 90 holiday homes that cater to pets in Near South Side. Several of our pet-friendly holiday homes even have a garden for your four-legged fur baby to run around in, complimentary treats, doggie beds and proximity to parks or green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Bookabach.
Can I rent a house with a pool in Near South Side?
Add an extra element of fun to your getaway by booking your crew into one of the 31 houses with a private pool in Near South Side. Use our handy search filter to find the kind of property you want on Bookabach, and then spend carefree days splashing about in a swimming pool that's all your own.
What are popular home amenities in Near South Side?
The most popular home amenities guests are looking for in Near South Side include nearby museums, a lake view and a nearby river. Whether you're holidaying with family, buddies or even pets, Bookabach holiday properties provide the best amenities for chilling out with the people you cherish the most.
Are there large group holiday homes in Near South Side?
With 36 Near South Side holiday homes that can host five or more people, you can bring a few extra family members or pals along. Whether you're planning an informal gathering or a birthday party, Bookabach will help you find a comfy space to match the occasion.
Are there holiday homes in Near South Side that welcome kids?
With 90 family-friendly holiday homes to choose from in Near South Side, now is a great time to introduce your children to the joys of travel. Just check our "Properties good for families" filter box to browse stays packed with amenities ideal for families on the move, such as multiple bedrooms, swimming pools, hot tubs and entertainment areas.
What are the top attractions for families in Near South Side?
Keep your kids entertained at these popular family-friendly attractions in Near South Side:
  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium
Are there one-bedroom holiday homes in Near South Side?
Yes, you can take your pick from 30 one-bedroom homes in Near South Side. Whether you're on the lookout for a cosy chalet or a cabin, Bookabach's one-bedroom properties are just right if you don't need lots of space. One of the major perks of having your own digs? You'll never need to share your trip with strangers.
Can I find two-bedroom holiday homes in Near South Side?
You can select from 34 two-bedroom holiday homes in Near South Side. Put the kids in the second room or maybe fill it with a couple of your nearest and dearest friends. There's a comfy spot for whoever's fortunate enough to be coming along.
Are there holiday homes with WiFi in Near South Side?
Near South Side has 31 holiday homes with WiFi, so you'll be able to stay connected during your holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with the family to scrolling social media, these Bookabach homes will keep you online.
How can I find holiday homes with air conditioning in Near South Side?
You'll find 85 holiday homes with air conditioning in Near South Side giving you that cooling breeze and extra comfort level. Just enter your preferred travel dates and then make use of our filters to help you book stays with air conditioning.
How old do you have to be to rent a holiday home in Near South Side?
We recommend you check with the Near South Side holiday property you want on Bookabach as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Near South Side for?
The length of time you can rent a holiday home in Near South Side depends on the property. Just enter your desired travel dates to view a list of options offering extended stays. With many amenities like air conditioning and full kitchens, as well as some offering discounted weekly or monthly prices, you're sure to find the perfect place to call your home away from home in Near South Side.

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