South Loop holiday homes

We found 426 holiday rentals — enter your dates for availability

Discover a selection of 297 apartments, 34 flats and other holiday rentals in South Loop that are perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a pool. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - South Loop

Showing deals for:19 Dec - 26 Dec
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Why visit South Loop

  • Urban parks: Enjoy the lush green spaces perfect for family outings and nature walks.
  • Iconic architecture: Marvel at impressive skyscrapers and historic buildings that define the skyline.
  • Cultural experiences: Immerse yourself in the diverse art and cultural offerings unique to the area.
  • Scenic strolls: Take a relaxing walk along Waituna Lagoon and explore the picturesque Coastal Southland.
  • Friendly atmosphere: Experience the welcoming locals and vibrant community that make South Loop special.

Top attractions near South Loop

South Loop in Chicago is an excellent choice for families and business travellers alike, offering a mix of urban parks, impressive skyscrapers, and historic buildings. With plenty of cultural experiences to explore, you can enjoy outdoor activities, scenic spots, and nature walks. Whether you're after a family outing or a day trip, South Loop has something for everyone, making it a perfect destination for your next holiday.

  • Grant Park: A vibrant urban park, Grant Park offers a family-friendly atmosphere with plenty of outdoor space to relax and enjoy the city vibes. It's perfect for a leisurely stroll or a picnic.
  • Buckingham Fountain: This historic fountain is a cultural gem, showcasing stunning architecture and impressive water displays. It's a must-see for those interested in Chicago's rich history.
  • Adler Planetarium and Astronomy Museum: A fantastic space park, the Adler Planetarium provides a thrilling experience for families and entertainment enthusiasts alike, featuring engaging exhibits about the universe.

Things to do recommended for couples

Looking for a romantic getaway in South Loop? Enjoy live music at the House of Blues Chicago or indulge in a meal at the historic Michael Jordan Restaurant, perfect for couples. For more entertainment, head to the Aragon Ballroom for an unforgettable night out together.

Things to do recommended for families

Your family will love exploring Soldier Field, a mere 805m from South Loop, soaking in the sports atmosphere. For a bit of nature, visit the Northerly Island Natural Area, just 1.6km away, offering a perfect spot for relaxation and wellness.

Things to do recommended for groups

Experience the vibrant culture of Chicago by catching a show at the Chicago Theatre, just 3.2km from South Loop. For a laugh, head to Second City, 4.8km away. Don’t forget to explore Chicago Place Mall, also 3.2km away, for some shopping fun with the group.

*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 South Loop

If you're planning a trip with a group, family, or pets, or if you're seeking longer accommodation options, be sure to refine your search based on what matters most to you. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to South Loop with a group: Think about how many bedrooms you’ll require and any additional features like a full kitchen or outdoor area for group gatherings. The good news is that you can easily filter for these options and more on Vrbo.
  • Traveling to South Loop with young kids: Travelling with young kids can be a bit tricky. It's important to prioritise their comfort and safety, along with age-appropriate facilities like private swimming pools. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to South Loop: For many, a family holiday wouldn’t be the same without their furry companion. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting South Loop: If you’re on the hunt for holiday 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 long-term rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near South Loop

South Loop, Chicago offers a vibrant blend of urban charm and family-friendly activities, perfect for a memorable holiday. You can explore the bustling South Loop District, take a scenic stroll along Waituna Lagoon, or venture to the picturesque Coastal Southland. With its friendly locals and diverse atmosphere, you'll find a delightful mix of business and leisure just a minute's walk away. Discover the essence of this dynamic neighbourhood and create lasting memories.

  • Chicago: Chicago, the vibrant heart of Illinois, is a city known for its rich cultural scene and diverse attractions. Situated in the South Loop, this metropolis offers a family-friendly atmosphere packed with outdoor activities and city-themed experiences. Visitors can enjoy renowned shopping areas, thrilling arena entertainment, and captivating theatre performances. Notable landmarks include the iconic stadiums and sports facilities that host major events, alongside bustling tourist precincts that showcase the city’s dynamic spirit.
  • Downtown Chicago: A mere 3.2km from South Loop, Downtown Chicago is a lively neighbourhood that embodies the city's urban charm. This area is perfect for families and outdoor enthusiasts, featuring an array of shopping options, entertainment venues, and theatres. Attractions nearby include popular tourist precincts, sports stadiums, and vibrant public spaces, making it an ideal spot for exploring the city’s heartbeat. With its impressive skyline and lively atmosphere, Downtown Chicago is a must-visit for anyone looking to experience the essence of the city.
  • The Loop: Just 3.2km from South Loop, The Loop is the bustling downtown area of Chicago, renowned for its iconic architecture and cultural landmarks. Families will find plenty of outdoor activities and city-themed attractions, including shopping districts and lively theatres. The Loop is home to significant urban parks that provide a refreshing escape amidst the urban landscape, alongside stadiums that host thrilling sporting events. This neighbourhood is perfect for those who wish to immerse themselves in the rich history and vibrant energy of Chicago.

Best time to go to South Loop

If you're planning a trip to South Loop, it's a good idea to check both the weather and property rates. The warmest month is July.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudyAverage
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudyAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverage
May57.0°F (13.9°C)Light RainMostly SunnySlightly High
June67.3°F (19.6°C)Light RainMostly SunnySlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly High
August73.0°F (22.8°C)Light RainMostly SunnyAverage
September67.1°F (19.5°C)Light RainMostly SunnyAverage
October54.9°F (12.7°C)Light RainMostly SunnySlightly Low
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is a breeze

Are you keen to save on your next getaway? Being flexible with your travel dates can make a real difference, as prices often fluctuate. You might also find great deals by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board offers a handy platform for planning your next adventures, allowing you to easily pick up from where you last left off or organise your travel arrangements. You can view your saved or booked properties, neatly sorted into Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday home accommodation in South Loop?
The most popular types of holiday homes in South Loop are apartments. After something a little different? Bookabach has plenty of options to match the diverse needs of our guests, so you'll see properties in lots of shapes and sizes. The ideal fit is ready and waiting for you — book yours today.
How much does it cost to rent a holiday home in South Loop?
Different factors determine what you'll pay for your holiday home in South Loop, such as the type of property, season and length of stay. But, all our holiday homes have something in common — incredible value. Simply enter your travel dates to find your dream escape.
How much does it cost to rent a beach house in South Loop?
The average price for a holiday home close to the beach in South Loop depends on when you're travelling and the type and size of property you're searching for. You can quickly and easily find prices on Bookabach by entering your travel dates. Then use the handy filters to pick the number of bedrooms and amenities that you require, like air conditioning, WiFi and a hot tub.
Are there pet-friendly holiday homes in South Loop?
Pack up a suitcase for your pooch because South Loop has 148 properties that roll out the welcome mat to pets. Let your four-legged friend join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.
Can I rent a house with a pool in South Loop?
Dig out your swimwear and pool noodle, because there are 36 houses with a private pool in South Loop. Settle in at one of these sought-after holiday homes and make every day a pool day. Simply enter your dates into Bookabach, then check the "pool" filter to find the perfect place for a splashing good time!
What are popular home amenities in South Loop?
Nearby museums, a nearby river and a sauna head the list of most popular home amenities in South Loop. Whether you plan to travel as a party of one, with your other half or as a family, Bookabach will help you find a holiday home that fits your style with all the features you need.
Are there large group holiday homes in South Loop?
Pick from two holiday properties in South Loop that can accommodate 10 or more people. Whether you're organising a trip with the family or a celebration like a birthday, there's plenty of room to get your group together under one roof.
Are there holiday homes in South Loop that welcome kids?
Gather the whole crew for an adventure in South Loop at one of our 148 family-friendly holiday homes. A lot of these stays feature amenities that are perfect for getaways with the little ones, including laundries, extra bedrooms and swimming pools. Simply click on the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in South Loop?
Keep the kids amused at these fabulous family-friendly attractions in South Loop:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in South Loop?
You'll find 57 one-bedroom properties in South Loop to pick from. A one-bedroom holiday home is a wonderful choice if it's just two of you or if you're holidaying solo. Add in more space, privacy and convenience compared to a regular hotel, and you've got yourself an unforgettable break.
Can I find two-bedroom holiday homes in South Loop?
Pick from 46 two-bedroom homes in South Loop. Give the kids the second room or maybe fill it with a couple of your favourite people. There's a comfy spot for whoever's fortunate enough to be joining in on the fun.
Are there holiday homes with WiFi in South Loop?
Whether you want to keep up with world events, check emails or post a pic to social media, there are 42 holiday homes with WiFi in South Loop. Check the "WiFi" box when searching on Bookabach and stay connected on your getaway.
How can I find holiday homes with air conditioning in South Loop?
South Loop has 143 holiday homes where you can relax and recharge in air-conditioned comfort. To find a stay on Bookabach that features this amenity, enter your dates of travel and use the filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in South Loop?
The minimum age is typically 16, 18 or 21. It can differ across properties on Bookabach, so look at the rules of your chosen South Loop stay before booking your escape.
How long can I rent a holiday home in South Loop for?
The length of time you can rent a holiday home in South Loop varies according to the property. Simply enter your preferred dates to see a list of options offering extended stays. With many amenities such as laundries and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to find a perfect place to call your home away from home in South Loop.

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