Near South Side holiday lettings

We found 1,513 holiday rentals — enter your dates for availability

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.

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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

What is the most popular type of holiday rental in Near South Side?
In Near South Side, apartments are the most popular type of holiday rental, with around 165 available in this vibrant neighbourhood. These apartments typically feature modern amenities such as fully equipped kitchens, spacious living areas, and convenient access to local attractions like the Museum Campus and the historic Prairie Avenue. For those seeking more space, there are about 27 holiday houses that cater to families or groups, offering multiple bedrooms, private gardens, and outdoor seating areas for relaxation. Additionally, there are 11 condominiums available, which often include shared amenities such as fitness centres and pools.
Are there any beach house rentals in Near South Side?
In Near South Side, Illinois, there are several beach house rentals available, offering a great experience close to the waterfront. These properties typically feature spacious interiors with multiple bedrooms, fully equipped kitchens, and living areas designed for relaxation after a day of exploring the nearby attractions. Many rentals also boast outdoor spaces such as decks or patios, great for enjoying the views of the city skyline or the lake. The area is conveniently located near points of interest like the Museum Campus, which includes the Field Museum and the Shedd Aquarium, making it an ideal spot for families and groups seeking both leisure and culture during their stay.
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?
May is the most popular time to visit Near South Side, Illinois, when the city comes alive with vibrant energy and numerous outdoor events. This period falls within the peak season, which runs from April to June, drawing in visitors eager to experience the rich culture, art, and culinary delights the area has to offer. With comfortable temperatures in the mid-teens to low 20s Celsius, it's an ideal time for sightseeing, strolling through parks, and enjoying al fresco dining.

During May, travellers can take advantage of various festivals, including the renowned Chicago Memorial Day Parade, which showcases the city's community spirit. The pleasant weather also makes it great for exploring nearby attractions, such as the Field Museum or the stunning Grant Park, all within walking distance.

If you're looking for a more budget-friendly option, consider visiting in December. While this month may be quieter in terms of tourist traffic, it offers a unique charm with festive decorations and holiday events that create a warm, friendly space.
Are there any remote work holiday rentals in Near South Side?
In the Near South Side of Illinois, there are numerous remote work-friendly holiday rentals available, with around 165 options for travellers to consider. This area is well-suited for those who need to balance work and leisure, featuring properties that provide essential amenities for a productive stay. Many rentals come equipped with Wi-Fi, dedicated office spaces, and meeting rooms, ensuring that guests have a comfortable environment to work from. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
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?
In Near South Side, visitors can explore a range of attractions that highlight the area's rich cultural and historical significance. The Museum Campus is a major draw, home to renowned institutions such as the Field Museum, the Shedd Aquarium, and the Adler Planetarium, all of which offer engaging experiences for families and solo travellers alike.

Additionally, Grant Park, often referred to as Chicago's "front yard," provides expansive green spaces, walking paths, and hosts various festivals throughout the year. The area is also close to Soldier Field, where sports enthusiasts can catch a Chicago Bears game or attend special events.
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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
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.

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