Near South Side vacation rentals

We found 1,547 vacation rentals — enter your dates for availability

Discover a selection of 10 homes, 188 apartments, and other vacation rentals in Near South Side that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as a hot tub and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Near South Side

Showing deals for:Apr 24 - May 1

Image gallery for Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Living area
9.2 out of 10, Wonderful, (63 reviews)
Wonderful
(63 reviews)

Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

Chicago

9% off
Price is $505
$3,534 for 7 nights
All fees included
Insta Worthy ^Prime Spot ^Patio ^Parking ^Fireplace

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Find out more about Near South Side

Why visit Near South Side

  • Cultural Experiences: Immerse yourself in the rich history and vibrant culture of Near South Side, showcasing a blend of modern charm and tradition.
  • Urban Parks: Enjoy the beautiful green spaces that offer relaxation and recreational activities for families and individuals alike.
  • Iconic Skyscrapers: Marvel at the stunning architecture of the city's iconic buildings that define Chicago's skyline.
  • Family-Friendly Activities: Discover a variety of attractions perfect for all ages, ensuring a fun-filled vacation.
  • Diverse Accommodation: Choose from stylish apartments and cozy homes, providing comfortable stays in a vibrant neighborhood.

Popular types of accommodation around Near South Side

Discover the perfect vacation rental in Near South Side with Vrbo. Whether you're looking for stylish apartments, cozy houses, or modern condos, we have a variety of options to suit your needs. Our travelers often explore south Chicago apartments and affordable rental options, ensuring a comfortable stay without breaking the bank. Dive into the vibrant culture of the South Side while enjoying the reassurance and transparency that comes with booking through our platform.

  • Apartments: The top choice for visitors to Near South Side, offering spacious and convenient living spaces for all types of travelers.
  • Houses: A popular option for families and groups, providing a home-like atmosphere with more privacy.
  • Condos: A favored selection for those seeking modern amenities and a central location, ideal for a city escape.
  • Cottages: These quaint and cozy retreats are perfect for a relaxing getaway.
  • Villas: An upscale choice, offering luxury accommodations for a lavish experience.**

Top attractions in and around Near South Side

Near South Side in Chicago is perfect for family, business, or entertainment-themed vacations. Visitors can explore a variety of attractions, including urban parks, iconic skyscrapers, and historic buildings. This vibrant area offers cultural experiences and family-friendly activities, making it an ideal destination for travelers seeking to immerse themselves in the city's rich history and modern charm.

  • McCormick Place: As one of the largest convention centers in North America, McCormick Place offers a dynamic atmosphere with world-class events, exhibitions, and conferences, all while showcasing stunning views of Lake Michigan.
  • Michigan Avenue: Known as the Mag Mile, this bustling street features premier shopping, dining, and iconic architecture, embodying the vibrant energy of Chicago's urban landscape.
  • Millennium Park: A beloved urban oasis, Millennium Park features beautiful gardens, art installations, and the famous Cloud Gate sculpture, perfect for family outings and outdoor activities.

Things to do recommended for couples

For a romantic getaway in Near South Side, enjoy live music at the House of Blues, only 2 miles away, or savor a meal at the Historic Michael Jordan Restaurant, also 2 miles away, perfect for a cozy dinner. Don't miss the energetic vibes.

Things to do recommended for families

Families visiting Near South Side can catch a game at Wrigley Field, relax at the Northerly Island Natural Area, or enjoy wellness activities at The East Bank Club, all offering fun and engaging experiences for travelers of all ages.

Things to do recommended for groups

Experience the vibrant culture at the Chicago Theatre, just 2 miles away, and enjoy a night of laughter at The Second City, 4 miles distant. For shopping enthusiasts, visit the Chicago Place Mall, located 3 miles away, offering a blend of family-friendly vibes and city excitement.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When you're traveling with a group, family, pets, or planning a longer stay, it's important to prioritize your needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Near South Side with a group: Think about how many bedrooms you require, along with additional amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Near South Side with young kids: Traveling with little ones can present some challenges. It's important to prioritize their comfort and safety, along with suitable amenities, 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 vacation isn’t truly a family affair without their furry companion. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that every member of your family feels at home.
  • Planning for a long term stay visiting Near South Side: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Near South Side

Near South Side, Chicago, offers a vibrant blend of urban life and scenic beauty, making it an ideal destination for families and business travelers alike. Explore the friendly neighborhoods, immerse yourself in the local culture, and enjoy the diverse entertainment options. Nearby areas also provide a welcoming atmosphere perfect for those seeking a family-friendly experience or a bustling city vibe. Discover the charm of South Chicago and the rich tapestry of this remarkable region.

  • Chicago: As the third-largest city in the United States, Chicago is a vibrant urban hub rich in culture and history. Located in the heart of the Midwest, Near South Side is part of this iconic city known for its stunning architecture and diverse neighborhoods. Travelers flock to Chicago for family-friendly activities, outdoor adventures, and city-themed experiences. Must-see attractions include the historic Soldier Field, the bustling shopping district on State Street, and world-renowned theaters. Enjoy a day at Millennium Park, catch a game at Wrigley Field, or indulge in the local culinary scene, all within easy reach.
  • Downtown Chicago: Just 2 miles from Near South Side, Downtown Chicago is the bustling core of the city. Known for its iconic skyline, this neighborhood offers an array of family-friendly, outdoor, and city-themed experiences. Visitors can explore the expansive shopping options along the Magnificent Mile, enjoy live performances at the Chicago Theatre, and take in the views from the Willis Tower Skydeck. The area is also home to major sports venues, making it a perfect spot for sports enthusiasts and entertainment seekers alike.
  • Prairie District: Located a mere 0.3 miles from Near South Side, the Prairie District is a charming neighborhood that blends family, entertainment, and business experiences. This area is known for its close proximity to event venues and convention centers, making it ideal for both leisure and business travelers. Explore the local theaters and enjoy a night out at the nearby arena entertainment facilities. The district is also home to beautiful parks and scenic views, providing a peaceful escape amidst the city buzz.

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

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Unlock savings with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll earn OneKeyCash on the full booking amount. Being the organizer truly has its rewards. Enroll in our One Key rewards program to unlock exclusive member discounts and earn OneKeyCash on eligible stays. Sign up today and begin your journey to savings.

Vrbo Trips: Planning made easy

Vrbo's user-friendly Trip Board offers you a dedicated space to plan exciting new getaways, pick up right where you left off, or manage and organize your travel plans. You can easily find the properties you’ve saved and booked in the sections for Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Near South Side?
In Near South Side, apartments are the most popular type of vacation rental, with approximately 173 available throughout the area. These apartments are typically located in vibrant neighborhoods close to attractions like the Museum Campus and the historic architecture of the area. Most rooms come with modern amenities, including fully equipped kitchens, comfortable living spaces, and often access to fitness centers or rooftop terraces for enjoying views of the Chicago skyline. For those seeking more space, there are around 19 vacation houses available, which generally feature multiple bedrooms, private yards, and outdoor seating areas—ideal for families or larger groups.
Are there any beach house rentals in Near South Side?
In Near South Side, Illinois, there are about 19 beach house rentals available, primarily situated near the waterfront and local parks. These vacation homes generally feature spacious layouts with multiple bedrooms, fully equipped kitchens, and living areas designed for relaxation. Many properties boast outdoor spaces such as patios or balconies, allowing guests to enjoy views of the lake and city skyline.
How much does it cost to rent a vacation home in Near South Side?
Prices for vacation 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 vacation 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.
What are popular rental amenities in Near South Side?
In Near South Side, popular vacation rental amenities include fully equipped kitchens, allowing travelers to prepare their own meals. Many rentals also feature coffee and tea makers for a cozy start to the day. Guests can enjoy outdoor spaces, as many properties come with patios, superb for relaxing or entertaining. For those looking to maintain their fitness routine, several rentals offer access to fitness facilities. Additionally, onsite parking is commonly available, making it convenient for guests with vehicles.
Are there any family house rentals in Near South Side?
In the Near South Side of Illinois, travelers will find a variety of family-friendly house rentals, with around 130 options available. This vibrant area offers easy access to attractions like Grant Park, where families can enjoy outdoor activities, and the Field Museum, superb for a day of exploration and learning.

Many of these homes feature spacious living rooms and fully equipped kitchens, allowing families to prepare meals together and enjoy quality time. Some properties also boast amenities such as private outdoor spaces, ideal for kids to play and for parents to relax.
Can I rent a vacation home with a pool or hot tub in Near South Side?
In Near South Side, Illinois, travelers will find a range of vacation homes available for rent that feature both pools and hot tubs, with around 40 options to choose from. This vibrant neighborhood offers a mix of urban convenience and recreational opportunities. Many properties come equipped with private pools and hot tubs, superb for relaxation after a day of exploring the city.

Expect amenities such as spacious living areas, fully equipped kitchens, and outdoor patios ideal for entertaining or enjoying family time. Some rentals may also include features like barbecue grills and cozy fire pits, enhancing the overall experience.
Are there any Near South Side vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Near South Side with parking available—perfect for families or travelers 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.
Are there pet-friendly vacation rentals in Near South Side?
In the Near South Side of Chicago, travelers will find a variety of pet-friendly vacation rentals available, with options that cater to different preferences and group sizes. Many of these rentals come equipped with modern amenities such as fully equipped kitchens, spacious living areas, and access to laundry facilities, ensuring a comfortable stay. The area is known for its proximity to attractions like Grant Park and the Museum Campus, which includes the Field Museum and the Shedd Aquarium, making it a great choice for those looking to explore the city with their pets.

Additionally, the nearby Burnham Park offers ample green space for walks and playtime, and there are several pet-friendly cafes and shops in the vicinity, enhancing the overall experience for pet owners.
Can I find long-stay vacation rentals in Near South Side?
A long-stay vacation rental in Near South Side is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Near South Side for a vacation rental?
The best time to visit Near South Side, Illinois, is during the vibrant spring months of April to June, with May being particularly popular for vacation rentals. This season is bustling with activities, as the city comes alive with festivals, art shows, and outdoor events, making it an ideal time for travelers seeking both adventure and cultural experiences.

During these months, the weather is generally pleasant, with temperatures ranging from the mid-50s to the low 80s Fahrenheit. This comfortable climate is superb for exploring the area's attractions, such as the iconic Grant Park, the stunning architecture along Michigan Avenue, and the lively atmosphere of the local markets. Whether you're strolling through the parks or enjoying an outdoor dining experience, you'll find plenty to keep you engaged.

For those looking for a more budget-friendly option, December offers a unique charm with festive decorations and holiday events. It's a quieter time to explore the Near South Side, allowing you to appreciate its offerings without the hustle and bustle of peak season.

Ultimately, your choice of when to visit Near South Side will depend on whether you prefer the energetic atmosphere of spring or the cozy, festive vibe of winter.
Are there any remote work vacation rentals in Near South Side?
In the Near South Side area of Illinois, travelers looking for remote work vacation rentals will find a variety of options, with around 141 available in the vicinity. This neighborhood, known for its proximity to downtown Chicago and cultural attractions, provides a conducive environment for remote work. Many rentals come equipped with essential amenities such as high-speed Wi-Fi, dedicated office spaces, desks, and comfortable chairs, allowing for a productive work environment. Some properties may even feature additional perks like laptop workspaces, computer monitors, and access to conference rooms or business centers.

The Near South Side is conveniently located near points of interest such as the Museum Campus, which includes the Field Museum and Shedd Aquarium, providing opportunities for relaxation and inspiration after work hours. Additionally, the area's vibrant dining scene and parks, such as Grant Park, enhance the overall experience for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Near South Side vacation rental?
Book your Near South Side vacation 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 vacation 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 several top attractions. The Museum Campus is a highlight, featuring the Field Museum, Shedd Aquarium, and Adler Planetarium, all within walking distance of one another. This area is great for those looking to immerse themselves in science, history, and marine life.

Grant Park, often referred to as "Chicago's front yard," is another significant attraction, offering vast green spaces, walking paths, and cultural landmarks like the Art Institute of Chicago. The nearby historic Buckingham Fountain is also a popular photo spot.

For sports enthusiasts, the United Center, located just northwest of the neighborhood, hosts Chicago Bulls and Blackhawks games. Additionally, the area is close to the vibrant entertainment and dining options of the South Loop, making it a convenient location for visitors seeking both culture and nightlife.
Can I change or cancel my Near South Side home rental booking on Vrbo?
To find Near South Side vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.Vrbo also offers support via live chat through our Help Center, 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 organizing 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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