Near South Side holiday lettings

We found 1,490 holiday rentals — enter your dates for availability

Discover a selection of 10 homes, 188 apartments 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:29 May - 5 Jun

Image gallery for Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

Interior
10 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)

Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

Chicago

7% off
Price is £21,678
for 7 nights, 1 home
£3,097 per night
includes taxes & fees
Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

Find spaces that suit your style

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    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Near South Side

  • Cultural experiences: Immerse yourself in the vibrant local culture with museums, galleries, and historic sites that reflect Chicago's rich heritage.
  • Urban parks: Enjoy leisurely strolls in lush parks, perfect for families and those seeking a respite from city life.
  • Iconic architecture: Marvel at the stunning skyscrapers and historic buildings that define the Chicago skyline.
  • Family-friendly activities: Engage in a variety of activities suitable for all ages, ensuring a memorable holiday for everyone.
  • Convenient accommodation: Choose from a range of comfortable lodgings, including apartments and holiday homes, tailored to your needs.

Popular types of accommodation around Near South Side

Planning a getaway to Near South Side? The excitement begins with selecting the perfect place to stay. Explore an array of popular accommodations, including apartments, private holiday homes, and condos. Whether you're searching for house rentals or homes for rent in Chicago, you're sure to find the ideal option that suits your needs and budget. Dive into your adventure with confidence and comfort!

  • Flats: The top choice for visitors in Near South Side, offering a home-like atmosphere with modern amenities.
  • Private Holiday Homes: A popular selection for families and groups seeking more space and privacy during their stay.
  • Condos: These stylish and comfortable units provide a convenient option for those wanting a blend of hotel-like services and home comforts.
  • Cottages: A delightful choice, perfect for those seeking a quaint and charming retreat.
  • Villas: Ideal for a luxurious getaway, offering ample space and upscale features for a memorable experience.**

Top attractions in and around Near South Side

Near South Side in Chicago is an excellent destination for family, business, and entertainment-themed holidays. Visitors can explore a variety of attractions, including urban parks, iconic skyscrapers, and historic buildings. This vibrant area caters to travellers seeking cultural experiences, family-friendly activities, and the dynamic essence of city life. Whether you're enjoying a leisurely stroll or delving into the local history, Near South Side has something for everyone.

  • McCormick Place: A premier convention centre, McCormick Place is known for its impressive scale and modern facilities, perfect for business events and conferences. Its dynamic atmosphere makes it a hub of activity, attracting professionals and visitors alike.
  • Grant Park: This expansive urban park is ideal for families and outdoor enthusiasts, featuring beautiful gardens, walking paths, and recreational areas. It serves as a serene escape in the city, often hosting events and festivals.
  • Chicago Riverwalk: A picturesque waterfront promenade, the Chicago Riverwalk offers stunning views and a variety of dining and entertainment options, making it a delightful spot for families and leisurely strolls along the river.

Things to do recommended for couples

For a romantic getaway in Near South Side, explore the vibrant House of Blues for an energetic concert or indulge in a meal at the Historic Michael Jordan Restaurant, perfect for couples. If you fancy a bit more distance, the Aragon Ballroom offers captivating music experiences just 5.0km away.

Things to do recommended for families

Your family will have a splendid time exploring Soldier Field, soaking in the sports atmosphere, and enjoying the natural beauty at Northerly Island Natural Area for some relaxation. Don't miss a visit to The East Bank Club, a wonderful place for wellness and leisure, just 1.9km away.

Things to do recommended for groups

Experience the vibrant culture of Chicago at the Chicago Theatre, just 1.2km away, or enjoy a night of laughter at Second City, located 2.5km from Near South Side. For shopping enthusiasts, Chicago Place Mall, 1.9km away, offers a delightful retail experience for the whole group.

What do I need to keep in mind when booking a vacation around Near South Side

Regardless of whether you're travelling with a group, as a family, bringing your pets, or seeking extended stays, it's important to apply the appropriate filters based on your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Near South Side with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Near South Side with young kids: Traveling with young children can present its challenges. It's important to prioritise their comfort and safety, as well as access to suitable facilities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Near South Side: For many families, a holiday isn't truly fulfilled without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and beds, ensuring that all members of the family feel comfortable and at home.
  • Planning for a long term stay visiting Near South Side: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Near South Side

Exploring Near South Side, Chicago offers a delightful mix of urban charm and family-friendly attractions. Visitors can immerse themselves in the vibrant local culture, enjoy stunning scenery, and experience the warmth of friendly locals. Don't miss the nearby South Chicago neighbourhood, where business and entertainment blend seamlessly, providing endless opportunities for adventure and relaxation. Whether you're here for leisure or work, Near South Side is a perfect base for discovering the rich tapestry of Chicago's South Side.

  • Chicago: Chicago is a bustling metropolis located approximately 1.2km from the Near South Side. Renowned for its vibrant culture, the city offers a plethora of attractions for families and outdoor enthusiasts alike. Visitors can indulge in extensive shopping experiences, catch an exhilarating game at the local sports facilities, or explore various educational venues. Iconic landmarks like stadiums and tourist precincts are easily accessible, making Chicago a fantastic destination for those seeking an urban adventure.
  • Downtown Chicago: Downtown Chicago, situated just 1.2km from the Near South Side, is the city's dynamic core. This neighbourhood is perfect for families and city explorers, offering a wide array of activities, including shopping, theatre performances, and visits to arena entertainment facilities. The area boasts impressive landmarks, such as sports stadiums and tourist precincts, ensuring that visitors have an unforgettable experience filled with excitement and culture.
  • The Loop: The Loop, also located around 1.2km from the Near South Side, serves as a central hub for those looking to immerse themselves in the city's urban landscape. Families and outdoor lovers will appreciate the diverse offerings, from vibrant shopping areas to engaging theatre shows. The Loop is home to notable attractions such as urban parks and stadiums, providing ample opportunities for relaxation and entertainment in the heart of Chicago.

Best time to go to Near South Side

If you're planning a trip to Near South Side, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April to May and July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyLowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyHighAverage
May57.0°F (13.9°C)Light RainMostly SunnyHighAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnyHighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverageSlightly High
September67.1°F (19.5°C)Light RainMostly SunnyAverageAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnyLowAverage
December33.1°F (0.6°C)Light RainMostly CloudyLowAverage

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming holiday? Being flexible with your travel dates can make a significant difference, as prices often vary. Additionally, opting for a longer stay typically leads to substantial savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board provides you with a dedicated space to plan new getaways, pick up from where you last stopped, or review and organise your travel arrangements. You can easily access properties you've saved or booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

How much does it cost to rent a holiday home in Near South Side?
Prices for holiday rentals 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Near South Side to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Near South Side holiday house rentals?
You can find great discounts on house rentals in Near South Side on Vrbo, 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.
Are there any Near South Side holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals 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 on Vrbo 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.
Can I find long-stay holiday rentals in Near South Side?
A long-stay holiday rental 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
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.
How early should I book a Near South Side holiday rental?
Book your Near South Side holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
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.
Can I change or cancel my Near South Side home rental booking on Vrbo?
To find Near South Side holiday rentals with free cancellation, just use Vrbo'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". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo 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, Vrbo 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 Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Near South Side holiday rental prices shown on Vrbo?
Vrbo 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.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, 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.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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