Near South Side vacation rentals

Why visit Near South Side

1. Cultural Experiences: Immerse yourself in the vibrant atmosphere with local art, music, and engaging virtual tours.
2. Family-Friendly Attractions: Enjoy a variety of activities suitable for all ages, from parks to educational sites.
3. Unique Accommodations: Choose from cozy apartments to spacious vacation homes tailored to your needs.
4. Shopping Opportunities: Explore nearby shopping districts, including the famous Magnificent Mile.
5. Scenic Beauty: Discover the charm of local neighborhoods and the picturesque Near North Side.

Popular types of accommodation around Near South Side

If you're looking for the perfect vacation rental in Near South Side, you're in the right place! Our most popular accommodations include apart hotels, cozy apartments, and spacious houses. Whether you're searching for a studio apartment or a larger home in Chicago, we have something to suit every traveler's needs. Enjoy the comfort and convenience of our carefully selected options, designed to make your stay memorable.

• Apartments: The top choice for visitors in Near South Side, offering a comfortable and convenient stay with amenities for all types of travelers.
• Houses: A fantastic option for those seeking more space and privacy, ideal for families or groups enjoying a home-like atmosphere.
• Condos: These stylish units provide a blend of luxury and convenience, perfect for travelers wanting a modern living experience.
• Cottages: A quaint and cozy option, great for those looking to unwind in a charming setting.
• Caravan Parks: A unique way to experience the outdoors while staying close to the city, suitable for adventurous travelers.**

Top attractions around Near South Side

Near South Side, Chicago, is perfect for family, business, and entertainment vacations, offering a range of attractions like urban parks, beaches, and conference venues. Visitors can enjoy cultural experiences while exploring the area's vibrant atmosphere. Don't miss out on optional virtual tours that provide unique insights into the local scene, making your trip engaging and memorable. Whether you're traveling solo or with loved ones, there's something for everyone in this dynamic neighborhood.

1. McCormick Place: This expansive convention center offers a unique blend of business and innovation, hosting various events and conferences. Its modern architecture and state-of-the-art facilities make it a hub for professionals and visitors alike.
2. Michigan Avenue: Known as the "Magnificent Mile," this bustling street is lined with premier shopping, dining, and cultural attractions. Experience the vibrant city atmosphere while exploring iconic landmarks and luxurious boutiques.
3. Navy Pier: A picturesque waterfront destination featuring stunning views, art installations, and family-friendly activities. It's the perfect spot for leisurely strolls, dining, and enjoying vibrant events throughout the year.

Things to do recommended for couples

For a romantic getaway in Near South Side, Chicago, enjoy a concert at the House of Blues or savor a meal at the Historic Michael Jordan Restaurant, both just 2 miles away. For more music, the Aragon Ballroom is a lively 8 miles from your location.

Things to do recommended for families

Families visiting Near South Side, Chicago can enjoy the excitement of Soldier Field, just 0.4 miles away, and unwind at the serene Northerly Island Natural Area, located 0.5 miles away. For more relaxation, the East Bank Club, 3 miles away, offers great recreational facilities for all ages.

Things to do recommended for groups

Experience the vibrant culture of Chicago by catching a show at the Chicago Theatre, indulging in shopping at 900 North Michigan Shops, or enjoying a night of laughter at Second City. These activities promise unforgettable moments for your group in the Near South Side.

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

When traveling with a group, family, pets, or planning an extended stay, it's important to use the right filters to prioritize your needs. Here are some helpful tips for booking on Vrbo.

• Traveling to Near South Side with a group: Think about how many bedrooms you'll require, along with features 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 young kids can be demanding. It's essential 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 trip isn’t truly enjoyable without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that your entire family feels comfortable and 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 rental options. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay around Near South Side

Near South Side, Chicago, offers a vibrant mix of family-friendly attractions and urban excitement. Explore the scenic beauty of the Near North Side, indulge in shopping along the Magnificent Mile, and enjoy the charm of local neighborhoods. With its welcoming atmosphere and diverse activities, this area is perfect for both relaxation and business. Discover the unique character of Chicago bungalows and immerse yourself in the friendly vibes that make this city truly special.

• Downtown Chicago: Downtown Chicago is a vibrant hub located 2 miles from Near South Side, brimming with family-friendly activities and outdoor experiences. As a central business district, it boasts a mix of shopping areas, theaters, and arena entertainment facilities. Major attractions include the iconic tourist precinct, where you can enjoy stunning city views, and various sports facilities, including a prominent stadium. Visitors can stroll along the Chicago Riverwalk, savor world-class dining, and immerse themselves in the city's rich cultural scene. Whether you're shopping on State Street or catching a show at the Chicago Theatre, Downtown offers an exciting urban experience.
• South Loop: Located a mere 0.6 miles from Near South Side, South Loop is an emerging neighborhood that caters to families and business travelers alike. Known for its proximity to educational institutions and event venues, this area features a mix of shopping districts and arena entertainment facilities. Key attractions include the convention center and various stadiums that host major events. The neighborhood also provides easy access to parks and outdoor spaces, perfect for a leisurely stroll or family outings. With its vibrant atmosphere and convenient access to public transport, South Loop is ideal for travelers seeking a mix of work and play.
• The Loop: The Loop, approximately 2 miles from Near South Side, is another exciting neighborhood offering a blend of family-friendly activities and city experiences. This bustling area is renowned for its shopping areas, theaters, and arena entertainment venues. Highlights include urban parks that provide a refreshing escape and a tourist precinct that showcases the city's architectural beauty. Visitors can explore Grant Park, often referred to as Chicago's "front yard," and enjoy outdoor concerts or festivals. The Loop is a perfect destination for those looking to experience the dynamic heart of Chicago while enjoying its rich cultural offerings.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	High	Slightly Low
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	High	Slightly High
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Average	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Low	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Low	Average

Booking with Vrbo is simple

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can 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.

Save more with One Key

Plan your group getaway by booking an eligible Vrbo and earn OneKeyCash™ on your entire reservation. Being the planner truly has its rewards! When you join our travel rewards program, One Key, you'll gain access to exclusive member discounts and accumulate OneKeyCash™ on qualifying bookings. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use platform for you to plan new trips, resume your previous ones, or manage your travel arrangements. You can conveniently view your saved or booked properties, organized into categories such as Potential, Upcoming, and Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.