Near South Side holiday homes

We found 1,499 holiday rentals — enter your dates for availability

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October 2025

November 2025

Discover a selection of 187 apartments, 11 flats 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:16 Jan - 23 Jan

Loft Living Space with Deep, Comfortable Sofa, Smart Flat Screen TV & Fireplace

Exceptional

(53 reviews)

Luxury House in the heart of Old Town with Parking

Chicago, IL

11% off

for 7 nights, 1 home

NZ$3,251 per night

includes taxes & fees

Exceptional

(92 reviews)

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

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$815 per night

includes taxes & fees

The apartment is flooded with beautiful light from multiple sides

Exceptional

(56 reviews)

Chic Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$461 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(61 reviews)

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$484 per night

includes taxes & fees

Huge, well designed condo that provides plenty of space and comfort!

Exceptional

(16 reviews)

River North 3BR/2BA: HUGE, Parking, Center Chicago

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$1,395 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(31 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$478 per night

includes taxes & fees

Enter into our large 1800 sq. ft. condo, featuring a game room. Perfect for you!

Exceptional

(30 reviews)

City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

Chicago, IL

11% off

for 7 nights, 1 apartment

NZ$1,272 per night

includes taxes & fees

Living Room / Dining Room with Fully stocked kitchen

Living Room has pullout couch (denim colored sofa)

Exceptional

(8 reviews)

Historic and Unique Brownstone in Gold Coast - 3

Chicago, IL

13% off

for 7 nights, 1 apartment

NZ$240 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Near South Side

McCormick Place

Find the best place to stay - Near South Side

McCormick 2B/2Ba for up to 8 guests w Opt Parking

Sleeps 8 · 2 bedrooms · 2 bathrooms

McCormick Place Skyline view 2b/2b unit with optional parking for up to 8 guests

Sleeps 8 · 2 bedrooms · 2 bathrooms

2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct

Sleeps 4 · 2 bedrooms · 2 bathrooms

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

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.