Near South Side vacation rentals

We found 1,490 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:May 29 - Jun 5

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

9% off
Price is $3,435
$24,042 for 7 nights
All fees included
Private, Discreet, Luxury Chicago Gold Coast Mansion, Event-Capable.

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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 vacation rental option, with about 166 available throughout the area. These apartments are conveniently located near attractions such as the Museum Campus and Soldier Field, offering guests easy access to local culture and events. Most units come equipped with modern amenities, including fully equipped kitchens, comfortable living spaces, and some even feature balconies for enjoying views of the city.

Additionally, there are several vacation houses and condos available, providing alternative options for travelers seeking more space or a different ambiance. These properties typically come with amenities such as outdoor areas, spacious living rooms, and multiple bedrooms, suiting families or groups looking for a home-like experience.
Are there any beach house rentals in Near South Side?
In Near South Side, several beach house rentals are available, primarily appealing to travelers seeking unique accommodations near the waterfront. These properties are often equipped with essential amenities such as fully stocked kitchens, comfortable living spaces, and outdoor areas for relaxation. While Near South Side is more urban in nature, visitors can enjoy nearby parks and access to Lake Michigan.
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, which allow guests to prepare their own meals during their stay. Many rentals also feature coffee and tea makers for a convenient morning routine. Fitness facilities are available in several properties, suiting those looking to maintain their exercise regimen while traveling. Onsite parking is another common amenity, providing ease of access for guests with vehicles. Additionally, many rentals offer travel cribs, making them family-friendly and accommodating for those traveling with young children.
Can I find family house rentals in Near South Side?
In the Near South Side area of Chicago, there are numerous family-friendly house rentals available—around 104 options for travelers to choose from. This vibrant neighborhood offers easy access to attractions such as the Museum Campus, where families can explore the Field Museum, Shedd Aquarium, and Adler Planetarium. Many of these homes provide spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces for children to play.

Visitors can also expect amenities like Wi-Fi, air conditioning, and laundry facilities, ensuring a comfortable stay. The proximity to parks and recreational areas encourages outdoor activities, making it an ideal location for families looking to enjoy both the city's cultural offerings and family-friendly environments.
Can I rent a vacation home with a pool or hot tub in Near South Side?
In the Near South Side of Chicago, there are several vacation homes available for rent that feature pools and hot tubs, with around 45 options to choose from. This vibrant area is known for its proximity to downtown attractions, cultural sites, and beautiful parks. Travelers can expect a range of amenities in these rentals, including private pools, relaxing hot tubs, spacious outdoor areas, and fully equipped kitchens, making them ideal for both relaxation and entertaining.
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.
Can I book pet-friendly vacation rentals in Near South Side?
Yes, there are numerous pet-friendly vacation rentals available in the Near South Side of Chicago, with around 60 options to choose from. This vibrant neighborhood offers a mix of modern amenities and easy access to local attractions. Travelers can expect rentals that feature spacious living areas, fully equipped kitchens, and outdoor spaces, making them suitable for both pets and their owners.

The Near South Side is conveniently located near several parks, such as Grant Park and the expansive Burnham Park, which are great for walks and outdoor activities with pets. Additionally, the area is close to pet-friendly cafes and shops, enhancing the overall experience for those traveling with their furry companions.
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 peak season from April to June, with May being particularly popular. This vibrant time of year draws travelers eager to explore the rich cultural offerings and lively option of the area. With pleasant temperatures typically ranging from the low 50s to mid-70s Fahrenheit, it's an ideal climate for outdoor activities, sightseeing, and enjoying the local parks.

During this peak season, you can immerse yourself in the neighborhood's art scene, visit iconic museums, and partake in various festivals that celebrate music and food. The bustling streets come alive with both locals and visitors, creating an engaging experience that showcases the best of Near South Side.

For those seeking a more budget-friendly option, consider planning your visit in December. Although this is a quieter month, it offers unique opportunities to enjoy the festive holiday decorations and cozy winter activities, all while experiencing the charm of the neighborhood in a more relaxed setting.

Ultimately, the best time to book a vacation rental in Near South Side will depend on whether you prefer the lively energy of the peak season or the peaceful ambiance of the quieter months.
Are there any remote work vacation rentals in Near South Side?
In the Near South Side area of Illinois, there are numerous remote work vacation rentals available, with around 123 options to choose from. This vibrant neighborhood is conveniently located near downtown Chicago, providing easy access to a variety of amenities and attractions. Many of the rentals in this area come equipped with essential remote work amenities such as high-speed Wi-Fi, dedicated workspaces, and even printers in some units, making it ideal for those looking to blend work and leisure.

Travelers can expect a range of accommodations, from modern apartments with open floor plans to cozy homes with inviting living spaces. Many properties also feature fully equipped kitchens, allowing for convenient meal preparation during extended stays. The Near South Side is close to points of interest like Grant Park, the Field Museum, and the Museum Campus, making it easy to explore cultural landmarks during downtime. 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, Illinois, United States of America?
In the Near South Side of Illinois, visitors can explore several top attractions that highlight the area's cultural and historical significance. The Museum Campus is a key highlight, where travelers can find the Field Museum, Shedd Aquarium, and Adler Planetarium, all within walking distance and offering a wealth of educational experiences.

The historic Soldier Field, home to the Chicago Bears, is also located in this neighborhood, providing opportunities for sports enthusiasts to catch a game or tour the stadium.

For those interested in the arts, the nearby Chicago Women's Park and Gardens offers a serene escape, featuring beautiful landscapes and sculptures, while the historic Prairie Avenue District showcases stunning architecture and homes from the late 19th century.
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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