Near South Side holiday homes

We found 1,419 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:15 Jan - 22 Jan

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

Historic luxury townhouse on Chicago's Gold Coast

Chicago

5% off
NZ$8,994
for 7 nights, 1 home
NZ$1,285 per night
includes taxes & fees
Historic luxury townhouse on Chicago's Gold Coast
French Bistro and Wine Bar - right downstairs
River North Luxury Living
Outdoors at night
The building
Exceptional
(107 reviews)

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

Chicago

7% off
NZ$6,067
for 7 nights, 1 apartment
NZ$867 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City
Exterior
Private kitchen
Living area
Dining
Wonderful
(24 reviews)

Chicago Grand Retreat - 6BR Near Downtown

Chicago

7% off
NZ$7,022
for 7 nights, 1 home
NZ$1,003 per night
includes taxes & fees
Chicago Grand Retreat - 6BR Near Downtown
Upstairs queen bedroom 2
Downstairs living area
Fun Mirror Wall Upstairs
Kitchen (upstairs)
Exceptional
(101 reviews)

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

Chicago

7% off
NZ$18,107
for 7 nights, 1 apartment
NZ$2,587 per night
includes taxes & fees
Luxurious Duplex Penthouse in the Heart of Chicago ~ Outstanding Location!
Room
Property grounds
Interior
Private kitchen
Exceptional
(8 reviews)

3bed/1 bath Retreat - 10 min from Downtown

Chicago

7% off
NZ$3,871
for 7 nights, 1 apartment
NZ$553 per night
includes taxes & fees
3bed/1 bath Retreat - 10 min from Downtown
Private kitchen
Living area
Interior
Room
Wonderful
(9 reviews)

The En Bronze ~ 7mins To Dining & Downtown Chicago

Chicago

7% off
NZ$7,445
for 7 nights, 1 apartment
NZ$1,064 per night
includes taxes & fees
The En Bronze ~ 7mins To Dining & Downtown Chicago
Enjoy your stay in the well appointed living room with a 55" Roku Smart TV
5 minutes drive to McCormick Place (0.9 miles)
Bedroom #1 with 2 double beds and an in-suite bathroom
Upscale kitchen with an equally spacious dining room
Wonderful
(9 reviews)

23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown

Chicago

7% off
NZ$4,264
for 7 nights, 1 apartment
NZ$609 per night
includes taxes & fees
23rd St - Modern 2 Bedroom with Parking - near McCormick Place, Chinatown
Bedroom #4 with a double and single bed
Living area
Well stocked kitchen with Keurig coffee maker, microwave, water filter and more
Close to the beautiful Ping Tom Park and a short water taxi ride to downtown
Exceptional
(22 reviews)

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

Chicago

7% off
NZ$6,513
for 7 nights, 1 apartment
NZ$930 per night
includes taxes & fees
1 #33 - 4 Bedroom / 2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
Dining
Living area
Room
Private kitchen
Wonderful
(9 reviews)

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

Chicago

7% off
NZ$3,733
for 7 nights, 1 apartment
NZ$533 per night
includes taxes & fees
Great Location. 5min to McCormick place. Downtown. Chinatown
Living area
Living area
Exterior
Room
Exceptional
(14 reviews)

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

Chicago

7% off
NZ$5,667
for 7 nights, 1 apartment
NZ$810 per night
includes taxes & fees
Cozy apartment near zoo, DePaul, Oz Park and much more!

  • 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

When is the best time to visit Near South Side for a holiday rental?
The best time to visit Near South Side, Illinois, is during the peak season from April to June, with May being particularly popular. This vibrant period attracts travellers keen to explore the area's rich cultural offerings, including art galleries, museums, and music festivals that come alive in the warmer weather. With temperatures ranging from 10 to 25 degrees Celsius, outdoor activities become a pleasure, allowing visitors to stroll through parks or dine al fresco at local eateries.May stands out as an ideal month for sightseeing, as the neighbourhood blossoms with events and festivities, making it an exciting time for both families and solo travellers. The allure of the nearby lakeshore adds an extra dimension, inviting leisurely walks and scenic views that enhance your holiday experience.For those looking for a more budget-friendly option, December offers a quieter atmosphere, superb for exploring the local charm without the crowds. The holiday lights and decorations create a festive ambience, allowing visitors to enjoy a different side of Near South Side.Ultimately, your choice depends on whether you prefer the bustling energy of spring and early summer or the peaceful charm of winter.
What are the top attractions in Near South Side, Illinois, United States of America?
In the Near South Side of Illinois, visitors can discover a range of attractions that highlight the area's vibrant culture and history. The Museum Campus is a major draw, featuring renowned institutions such as the Field Museum, the Shedd Aquarium, and the Adler Planetarium, all offering engaging exhibits and beautiful views of Lake Michigan.Nearby, the historic Prairie Avenue District showcases stunning architecture and offers a glimpse into Chicago's past, including the former home of the renowned architect Frank Lloyd Wright.For those interested in sports, the area is close to Guaranteed Rate Field, home to the Chicago White Sox, providing a lively option during the baseball season.Additionally, Grant Park, located to the north, features expansive green spaces and hosts various festivals and events throughout the year, making it a great spot for leisurely strolls and picnics.
Are all fees included in the Near South Side holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Near South Side holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Near South Side with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Near South Side holiday homes?
You can find great discounts on holiday homes in Near South Side on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Near South Side holiday home booking on Bookabach?
To find Near South Side holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Near South Side?
A long-stay holiday home in Near South Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Near South Side holiday home?
Book your Near South Side holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Near South Side?
Prices for holiday homes in Near South Side vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Near South Side to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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