Photo by Jihad F. Saleh

South Shore vacation rentals

We found 50 vacation rentals — enter your dates for availability

Discover a selection of 7 homes and other vacation rentals in South Shore that are perfect for your trip. Vacation rentals offer the amenities you expect for your stay with friends, family, or just your pet, such as parking and a hot tub. You're sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - South Shore

Showing deals for:Nov 14 - Nov 21
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Find out more about South Shore

Find out more about South Shore

Why visit South Shore

  1. Stunning outdoor spaces: South Shore features beautiful parks and beaches, perfect for family outings and relaxation.
  2. Rich cultural experiences: Engage with the vibrant local art scene and historical attractions that showcase the community's heritage.
  3. Diverse accommodations: Choose from a variety of vacation rentals, including cozy apartments and stylish condos to suit your needs.
  4. Community charm: Experience the unique vibes of South Shore, blending urban life with a welcoming neighbourhood atmosphere.
  5. Family-friendly activities: Enjoy a range of attractions that cater to all ages, ensuring fun for the entire family.

Popular types of accommodation around South Shore

Discover the charm of South Shore with a variety of vacation rentals to suit every traveller. Whether you prefer cozy apartments, spacious houses, or stylish condos, there’s something for everyone. Enjoy exclusive amenities and the allure of the South Shore Yacht Club, or consider the unique appeal of cooperative apartments and class enclaves. Your perfect getaway awaits, tailored to your needs and desires.

  • Apartments: The preferred choice for visitors to South Shore, offering convenient amenities and a home-like atmosphere.
  • Houses: A great option for groups or families seeking spacious accommodations with a personal touch.
  • Condos: Ideal for those who enjoy modern living spaces with added comforts and shared facilities.
  • Cottages: A delightful option for a quaint and peaceful getaway, perfect for relaxation.
  • Villas: Luxurious accommodations that provide an upscale experience for travellers looking to indulge.**

Top attractions around South Shore

South Shore, Chicago, is an ideal destination for outdoor family vacations, offering stunning scenery and a variety of attractions. Visitors can explore urban parks, historic houses, and beautiful beaches, all of which provide rich cultural and outdoor experiences. Whether you're seeking adventure or a relaxing day by the water, South Shore has something for everyone to enjoy. Don't miss the chance to immerse yourself in the local charm and vibrant community while you visit.

  1. McCormick Place: As a premier event and conference venue, McCormick Place is known for its impressive scale and modern facilities, hosting a variety of business events and conventions, just 11.3km from South Shore.
  2. University of Chicago: This historic university, located 4.8km away, boasts stunning Gothic architecture and a vibrant cultural atmosphere, making it a must-visit for history and art enthusiasts.
  3. Chicago Museum of Science and Industry: Only 3.2km from South Shore, this engaging museum offers hands-on exhibits that appeal to families and science lovers alike, fostering curiosity and exploration.

Things to do recommended for couples

For a romantic getaway in South Shore, explore the vibrant House of Blues for live music, indulge in a meal at the charming Grand Terrace Ballroom, or enjoy an evening concert at the Harold Washington Cultural Center. Each offers a unique and delightful experience for couples.

Things to do recommended for families

Families can immerse themselves in sports at Soldier Field, explore the serene Northerly Island Natural Area for relaxation, or enjoy activities at the Hammond Sportsplex & Community Center. Each location offers unique experiences, all within a short drive from South Shore, promising memorable family fun.

Things to do recommended for groups

Experience the vibrant arts at the Chicago Theatre, only 14.5km from South Shore, or try your luck at the Horseshoe Hammond Casino, just 9.7km away. For outdoor fun, enjoy a round of golf at the South Shore Golf Course, located right in the area.

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

When planning your travel, whether it’s with a group, family, pets, or for an extended stay, be sure to choose filters that align with your priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to South Shore with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor space for group activities. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to South Shore with young kids: Traveling with young children can present its own set of challenges. It’s important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, thinking about your location in relation to family-friendly attractions is a wise choice.
  • Taking your pets with you to South Shore: For many families, a vacation isn’t truly fulfilling without their furry companions. If you relate to this, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting South Shore: If you're in search of vacation rentals that offer discounts for month-long stays, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay around South Shore

South Shore, Chicago, offers a delightful blend of outdoor adventures and family-friendly attractions. Visitors can explore the scenic South Shore Park, enjoy the vibrant atmosphere of the neighbourhood, and experience local art and culture. With its unique vibes ranging from urban to business, South Shore is perfect for those seeking both relaxation and exploration. Don't miss the chance to discover the charm of this diverse community during your stay!

  • Jackson Park Highlands: Located a short 1.3km from South Shore, Jackson Park Highlands is a vibrant neighbourhood that offers a rich blend of family-friendly activities, outdoor adventures, and cultural experiences. Visitors can immerse themselves in the lush surroundings of urban parks and explore the historic college university nearby. The area is also home to a renowned arena entertainment facility that frequently hosts music concerts and events, making it a lively spot for both residents and tourists alike. With its charming streets and community spirit, Jackson Park Highlands is perfect for a leisurely stroll or an exciting family day out.
  • Essex: Situated 1.6km away from South Shore, Essex is a bustling neighbourhood known for its vibrant shopping areas and recreational spaces. This family-oriented locale provides a fantastic city experience with plenty of outdoor activities. Visitors can explore the local tourist precinct, which offers a variety of shops and eateries, or enjoy an afternoon at the recreational area. The arena entertainment facility is a highlight here as well, hosting various events that attract crowds. Essex is a great place to engage with the community and enjoy the lively atmosphere.
  • South Chicago: Just 3.2km from South Shore, South Chicago is a dynamic neighbourhood that caters to families and outdoor enthusiasts. Known for its rich cultural tapestry, visitors can enjoy the local education centres and recreational areas. The neighbourhood features a prominent stadium and sports facility, making it a hub for sporting events and community gatherings. Additionally, an event conference venue adds to the area's appeal, providing a space for various activities and exhibitions. South Chicago offers a unique blend of urban life and outdoor enjoyment, making it a must-visit during your trip.

Best time to go to South Shore

If you're planning a trip to South Shore, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in March to April and July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverageSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudySlightly HighSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnySlightly HighAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly 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 SunnySlightly LowAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is simple

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

Vrbo Trips: Planning made easy

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your travel arrangements, or manage your existing bookings. Your saved or reserved properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please visit: https://www.vrbo.com/en-ca/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental accommodation in South Shore?
The most in-demand types of vacation rentals in South Shore are apartments. Ready for more choices? Vrbo has numerous options to match our guests' unique requirements, so you'll see vacation properties in all sizes, and for all budgets. The ideal fit is waiting for you — discover yours today.
How much does it cost to rent a vacation rental in South Shore?
Property type, season and length of stay are some of the conditions that can influence the price of a vacation home. Simply enter your travel dates to find your ideal escape. From homey country cottages to expansive luxury villas, all Vrbo vacation rentals offer terrific value.
How much does it cost to rent a beach house in South Shore?
When you travel and the size and style of the property will determine the cost of your beachside stay. Enter your South Shore travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to pick the amenities and features you want in your beach house.
Are there pet-friendly vacation rentals in South Shore?
Happily, yes. Take your pick of six vacation rentals that welcome pets in South Shore on Vrbo. Our furry best friends also need a break, so simply use our search function for pet-friendly vacation rentals to find a pad where Fido can share in the good times.
What are popular rental amenities in South Shore?
A nearby river, a lake view and a firepit head the list of most popular rental amenities in South Shore. Whether you're taking to the road on your own, with your other half or a group of friends, Vrbo will help you find a vacation home that matches your tastes with all the extras you're looking for.
Are there large group vacation rentals in South Shore?
Yes, you'll find two vacation properties in South Shore that can accommodate five or more guests. From family trips to events like a friend's birthday, these stays have ample space to gather with the people that matter the most.
Are there vacation rentals in South Shore that welcome kids?
With six family-friendly vacation properties available in South Shore, 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 that come with amenities ideal for vacationing families, like living rooms, patios, bunk beds and hot tubs.
What are the top attractions for families in South Shore?
Keeping the kiddos entertained during your South Shore vacation is a cinch with these exciting family-friendly attractions:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Can I find two-bedroom vacation rentals in South Shore?
South Shore has two two-bedroom vacation rentals for you to pick from. Enjoy a vacation home with all the space and comfort you're looking for at a price that won't break the bank on Vrbo.
Are there vacation rentals with WiFi in South Shore?
South Shore has five vacation rentals with WiFi, so you'll be able to stay connected while you're traveling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to sending emails, these Vrbo homes make it a breeze to go online.
How can I find vacation rentals with air conditioning in South Shore?
South Shore has six vacation rentals where you can relax in air-conditioned comfort. To find a stay on Vrbo that provides this amenity, choose your travel dates and use the handy filters to select the "air conditioning" box.
How old do you have to be to rent a vacation rental in South Shore?
You'll have to check with the South Shore vacation home you're looking at on Vrbo as the age limit differs. However, it's normally 16, 18 or 21.
How long can I rent a vacation rental in South Shore for?
It's really down to the South Shore property. To look over a list of options offering extended stays, simply type your dates and guest number into Vrbo. Look forward to having the property to yourself, as well as amenities such as a full kitchen, air conditioning and an outdoor space where the kids can play. Be on the lookout for any long-term stays that offer weekly or monthly discounts.

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