
Near South Side holiday homes
We found 1,569 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:1 Aug - 8 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$87,081
NZ$87,081
NZ$12,440 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$104,981
NZ$104,981
NZ$14,997 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago

9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
8% off
Price is NZ$14,862
NZ$14,862
NZ$2,123 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$11,421
NZ$11,421
NZ$1,632 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)

1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$14,824
NZ$14,824
NZ$2,118 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$5,425
NZ$5,425
NZ$775 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago

9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,593
NZ$4,593
NZ$656 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
7% off
Price is NZ$13,128
NZ$13,128
NZ$1,875 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$15,997
NZ$15,997
NZ$2,285 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$8,985
NZ$8,985
NZ$1,284 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$11,788
NZ$11,788
NZ$1,684 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$15,526
NZ$15,526
NZ$2,218 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$9,680
NZ$9,680
NZ$1,383 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$5,425
NZ$5,425
NZ$775 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$4,593
NZ$4,593
NZ$656 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$4,593
NZ$4,593
NZ$656 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$5,425
NZ$5,425
NZ$775 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
8% off
Price is NZ$9,625
NZ$9,625
NZ$1,375 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$5,303
NZ$5,303
NZ$758 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
11% off
Price is NZ$13,127
NZ$13,127
NZ$1,875 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$6,324
NZ$6,324
NZ$903 per night
includes taxes & fees
Image gallery for 3BR/2BA Luxury Glass Apartment | Amazing Views

9.89.8 out of 10 rating
Exceptional
(35 reviews)
3BR/2BA Luxury Glass Apartment | Amazing Views
Chicago, Illinois
7% off
Price is NZ$14,028
NZ$14,028
NZ$2,004 per night
includes taxes & fees
Image gallery for 3/2 apt. w/ Rooftop | West Loop Chicago

8.68.6 out of 10 rating
Excellent
(16 reviews)
3/2 apt. w/ Rooftop | West Loop Chicago
Chicago, IL
11% off
Price is NZ$6,300
NZ$6,300
NZ$900 per night
includes taxes & fees
Image gallery for Toca Bella ~ 7mins to Downtown

1010 out of 10 rating
Exceptional
(11 reviews)
Toca Bella ~ 7mins to Downtown
Chicago, IL
7% off
Price is NZ$3,989
NZ$3,989
NZ$570 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
483 reviews(483 reviews)
Sentral Michigan Avenue
Sleeps 4 · 2 bedrooms
9.29.2 out of 10
Wonderfulwonderful
737 reviews(737 reviews)
McCormick Place Luxurious 5 bed/3 bath HUGE Suite for groups/up to 12 guests
Sleeps 12 · 5 bedrooms · 3 bathrooms
McCormick 2B/2Ba Large unit/8 guests w Opt Parking
Sleeps 8 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
South Loop 3 Bedroom Apt
Sleeps 8 · 3 bedrooms · 1 bathroom
7.87.8 out of 10
Goodgood
HUGE 5BR with Optional Parking/Pool table/sleeps 10
Sleeps 8 · 5 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
- 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.