Near South Side holiday lettings

We found 1,644 holiday rentals — enter your dates for availability

Discover a selection of 20 homes, 197 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:3 Oct - 10 Oct

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.

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.

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

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.

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 accommodation in Near South Side?
Apartments are the most popular style of holiday rental in Near South Side, according to our data. Even if you have something different in mind, Vrbo 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 rental 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 Vrbo holiday rentals offer incredible value.
How much does it cost to rent a beach house in Near South Side?
The average price for a holiday rental 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 Vrbo 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 rentals in Near South Side?
Yes. There are. You'll have your pick of 90 holiday rentals that cater to pets in Near South Side. Several of our pet-friendly holiday rentals 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 Vrbo.
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 Vrbo, and then spend carefree days splashing about in a swimming pool that's all your own.
What are popular rental amenities in Near South Side?
The most popular rental 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, Vrbo holiday properties provide the best amenities for chilling out with the people you cherish the most.
Are there large group holiday rentals 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, Vrbo will help you find a comfy space to match the occasion.
Are there holiday rentals in Near South Side that welcome kids?
With 90 family-friendly holiday rentals 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 rentals in Near South Side?
Yes, you can take your pick from 30 one-bedroom rentals in Near South Side. Whether you're on the lookout for a cosy chalet or a cabin, Vrbo'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 rentals 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 rentals with WiFi in Near South Side?
Near South Side has 31 holiday rentals 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 Vrbo homes will keep you online.
How can I find holiday rentals with air conditioning in Near South Side?
You'll find 85 holiday rentals 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 rental in Near South Side?
We recommend you check with the Near South Side holiday property you want on Vrbo as the minimum age differs. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Near South Side for?
The length of time you can rent a holiday rental 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.

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