
Near South Side holiday homes
We found 1,563 holiday rentals — enter your dates for availability
Discover a selection of 5 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:25 Jul - 1 Aug
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is NZ$68,819
NZ$68,819
NZ$9,831 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment

9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,663
NZ$11,663
NZ$1,666 per night
includes taxes & fees
Image gallery for Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago

9.69.6 out of 10 rating
Exceptional
(37 reviews)
Kasa | Relaxing 2 BD + Steps to the South Loop | Chicago
Chicago, Illinois
8% off
Price is NZ$10,149
NZ$10,149
NZ$1,450 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,386
NZ$5,386
NZ$769 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes

1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
8% off
Price is NZ$15,761
NZ$15,761
NZ$2,252 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking

1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,698
NZ$16,698
NZ$2,385 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

9.89.8 out of 10 rating
Exceptional
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,646
NZ$7,646
NZ$1,092 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views

8.88.8 out of 10 rating
Excellent
(20 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$11,092
NZ$11,092
NZ$1,585 per night
includes taxes & fees
Image gallery for 2BR Designer Loft: Modern Luxe in City Center

1010 out of 10 rating
Exceptional
(5 reviews)
2BR Designer Loft: Modern Luxe in City Center
Chicago, Illinois
8% off
Price is NZ$9,370
NZ$9,370
NZ$1,339 per night
includes taxes & fees
Image gallery for Kasa | Family Friendly 3 BD + Game Room Access | Chicago

9.69.6 out of 10 rating
Exceptional
(14 reviews)
Kasa | Family Friendly 3 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$13,934
NZ$13,934
NZ$1,991 per night
includes taxes & fees
Image gallery for Kasa | Inviting 1 BD + Game Room Access | Chicago

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Kasa | Inviting 1 BD + Game Room Access | Chicago
Chicago, Illinois
8% off
Price is NZ$8,116
NZ$8,116
NZ$1,159 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago

9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,386
NZ$5,386
NZ$769 per night
includes taxes & fees
Image gallery for Kasa | Classic 2 BD + Near Grant Park | Chicago

1010 out of 10 rating
Exceptional
(6 reviews)
Kasa | Classic 2 BD + Near Grant Park | Chicago
Chicago, Illinois
8% off
Price is NZ$10,149
NZ$10,149
NZ$1,450 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago

9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,556
NZ$4,556
NZ$651 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,556
NZ$4,556
NZ$651 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

9.49.4 out of 10 rating
Exceptional
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$8,594
NZ$8,594
NZ$1,228 per night
includes taxes & fees
Image gallery for Chic Corner 2BR in Streeterville | Roof Deck | Lake Views

9.69.6 out of 10 rating
Exceptional
(27 reviews)
Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$7,812
NZ$7,812
NZ$1,116 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago

1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,386
NZ$5,386
NZ$769 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,601
NZ$4,601
NZ$657 per night
includes taxes & fees
Image gallery for Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests

9.29.2 out of 10 rating
Wonderful
(10 reviews)
Skyline Duplex Penthouse w private rooftop & optional parking for up to 8 guests
Chicago, IL
12% off
Price is NZ$14,680
NZ$14,680
NZ$2,097 per night
includes taxes & fees
Image gallery for Cozy Pilsen Depa

1010 out of 10 rating
Exceptional
(23 reviews)
Cozy Pilsen Depa
Chicago, IL
8% off
Price is NZ$6,529
NZ$6,529
NZ$933 per night
includes taxes & fees
Image gallery for Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!

9.89.8 out of 10 rating
Exceptional
(82 reviews)
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Chicago, IL
8% off
Price is NZ$17,219
NZ$17,219
NZ$2,460 per night
includes taxes & fees
Image gallery for 3BR/2BA Luxury Glass Apartment | Amazing Views

9.89.8 out of 10 rating
Exceptional
(34 reviews)
3BR/2BA Luxury Glass Apartment | Amazing Views
Chicago, Illinois
7% off
Price is NZ$14,201
NZ$14,201
NZ$2,029 per night
includes taxes & fees
Image gallery for Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

1010 out of 10 rating
Exceptional
(18 reviews)
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
Chicago, IL
7% off
Price is NZ$4,032
NZ$4,032
NZ$576 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find properties near top attractions in Near South Side
Map Attractions

4
Field Museum of Natural History

5
Northerly Island Natural Area

6
Adler Planetarium and Astronomy Museum
Find the best place to stay - Near South Side
Sonder South Wabash
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
482 reviews(482 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
736 reviews(736 reviews)
McCormick 2B/2Ba Large unit/8 guests w Opt Parking
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Sleeps 12 · 5 bedrooms · 3 bathrooms
South Loop 3 Bedroom Apt
Sleeps 8 · 3 bedrooms · 1 bathroom
7.87.8 out of 10
Goodgood
McCormick 6B/4Ba Luxury Suite for groups of up to 12 guests w/ optional parking
Sleeps 12 · 6 bedrooms · 4 bathrooms
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore 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.