Near South Side vacation rentals

We found 1,496 vacation rentals — enter your dates for availability

Discover a selection of 8 homes 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:Jul 3 - Jul 10

Image gallery for Archer #2 | New 3 Bedroom near McCormick Place, Wintrust Arena, Chinatown

Living area
9.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)

Archer #2 | New 3 Bedroom near McCormick Place, Wintrust Arena, Chinatown

Chicago

8% off
Price is $300
$2,098 for 7 nights
All fees included
Archer #2 | New 3 Bedroom near McCormick Place, Wintrust Arena, Chinatown

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Find out more about Near South Side

Why visit Near South Side

  • Iconic Attractions: Discover famous landmarks in downtown Chicago, including the stunning skyline and historic buildings.
  • Urban Parks: Enjoy family-friendly activities and relaxation in beautiful urban parks throughout the area.
  • Cultural Experience: Immerse yourself in the rich cultural offerings and vibrant atmosphere of the Near South Side.
  • Welcoming Neighborhoods: Explore charming neighborhoods like South Shore and Chatham, known for their friendly locals.
  • Diverse Accommodations: Choose from a variety of vacation rentals for a comfortable and memorable stay.

Popular types of accommodation around Near South Side

Planning a getaway to Near South Side? You're in for a treat. This vibrant area offers a variety of popular vacation rentals, including cozy studio apartments, spacious one-bedroom units, and inviting condos. Whether you're looking for a fully-equipped private vacation home or a stylish il apartment, you'll find the perfect place to unwind. Dive into your options and enjoy a memorable stay in Near South Side.

  • Apartments: A favored choice among travelers, apartments offer a comfortable and convenient home base to explore Near South Side.
  • Houses: Perfect for families or groups, these homes provide ample space and privacy for a relaxing stay.
  • Condos: Stylish and often centrally located, condos are a great option for visitors seeking modern amenities.
  • Cottages: These quaint retreats provide a cozy atmosphere, ideal for a peaceful getaway.
  • Villas: Luxurious villas offer an upscale experience with spacious living areas and beautiful surroundings.**

Top attractions in and around Near South Side

Near South Side in Chicago offers a perfect blend of family-friendly activities, entertainment, and business opportunities. Visitors can explore urban parks, iconic skyscrapers, and historic buildings while enjoying a rich cultural experience. Don't miss the stunning Chicago skyline and the vibrant Chicago Loop. Consider renting accommodations by neighborhood for a more immersive stay, and be sure to request local tours to fully appreciate everything Near South Side has to offer.

  • Field Museum of Natural History: A fascinating natural history museum showcasing diverse exhibits, from ancient fossils to cultural artifacts. It’s perfect for families and those eager to explore the wonders of our planet.
  • Michigan Avenue: Known as the Magnificent Mile, this bustling street features upscale shopping, dining, and stunning architecture, embodying the vibrant city life of Chicago.
  • Navy Pier: A lively waterfront destination offering stunning lake views, entertainment, and dining, making it a great spot for enjoying urban scenery and friendly interactions.

Things to do recommended for couples

Planning a romantic getaway in Near South Side? Explore the beautiful Grant Park, take a sunset stroll along the lakefront, or enjoy a cozy dinner at a local bistro. Don't miss a visit to the Art Institute for a dose of culture and inspiration together.

Things to do recommended for families

Families can explore the interactive exhibits at the Museum of Science and Industry, delight in hands-on fun at the Children's Museum, or take a leisurely stroll through Grant Park's beautiful landscapes. Enjoy a day at the iconic Navy Pier, filled with rides and activities for all ages.

Things to do recommended for groups

Explore the vibrant Museum Campus, featuring the Field Museum, Shedd Aquarium, and Adler Planetarium. Enjoy a group bike ride along the scenic lakefront trail, or experience a thrilling Chicago sports event at nearby United Center. Don’t miss the iconic architecture boat tour for a unique city view.

*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 planning your trip, whether you're traveling with a group, family, pets, or seeking longer accommodations, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Near South Side with a group: Think about how many bedrooms you'll require, as well as any amenities like a full kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and much more on Vrbo.
  • Traveling to Near South Side with young kids: Traveling with young kids can be demanding. 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 fulfilling without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Near South Side: If you're searching for vacation rentals that offer discounts for month-long stays, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include preferences like a parking spot, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Near South Side

Near South Side, Chicago, offers a vibrant blend of urban energy and scenic charm, perfect for family and business vacations. Explore iconic attractions in downtown Chicago, unwind in the South Shore, or discover the quaint allure of the Chatham neighborhood. With friendly locals and a welcoming atmosphere, you'll experience the best of city life while enjoying family-friendly activities and beautiful scenery. Your adventure in and around Near South Side promises unforgettable memories.

  • Chicago: As one of the largest cities in the United States, Chicago offers a vibrant and diverse urban experience. Located in Illinois, Near South Side is nestled within this bustling metropolis, making it an ideal starting point for exploration. Visitors to Chicago can indulge in a variety of family-friendly activities, from shopping in the Magnificent Mile to enjoying performances at renowned theaters like the Chicago Shakespeare Theater. Notable attractions include the iconic Wrigley Field, the scenic Grant Park, and the bustling tourist precinct, all within easy reach. The city is also famous for its stunning architecture and lively sports culture, ensuring there’s something for everyone.
  • Downtown Chicago: Merely 2 miles from Near South Side, Downtown Chicago is the city's energetic nucleus, thriving with activity and excitement. This neighborhood is perfect for family outings and outdoor adventures, featuring a plethora of shopping options and entertainment venues. Visitors can catch a game at the United Center or explore the beautiful Millennium Park, home to the famous Cloud Gate sculpture. Shopping enthusiasts will appreciate the Michigan Avenue shopping district, while theater lovers can enjoy performances at the historic Chicago Theatre. With its vibrant atmosphere and variety of attractions, Downtown Chicago is a must-visit destination.
  • Prairie District: Just 0.3 miles from Near South Side, the Prairie District is a charming neighborhood that blends family-friendly and business-oriented experiences. Known for its entertainment options, this area boasts several theaters and event venues, making it an appealing spot for visitors. Guests can enjoy a night out at the nearby arena or explore the many shopping opportunities available. The district is also home to notable landmarks such as the historic Soldier Field and the expansive McCormick Place convention center, ensuring that visitors have a memorable stay filled with diverse attractions.

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 trip? Consider being flexible with your travel dates, as prices can fluctuate. Plus, booking a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to narrow down your search by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides you with a convenient area to plan new journeys, manage your existing arrangements, or review your reservations. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please 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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