South Loop holiday homes

We found 368 holiday rentals — enter your dates for availability
Discover a selection of 208 apartments, 20 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.

  • Peace of mind

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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

When is the best time to visit South Loop for a holiday rental?
The peak travel season in South Loop, Illinois, extends from May to July, with July being the most popular month for visitors. This vibrant period is characterised by a bustling atmosphere, as tourists flock to enjoy the area's cultural attractions, outdoor festivals, and numerous dining options. With pleasant temperatures averaging between 20 to 30 degrees Celsius, summer in South Loop is ideal for exploring the iconic parks, museums, and waterfront, making it a fantastic choice for those seeking both adventure and relaxation.For those who prefer a quieter experience, November presents a wonderful opportunity to visit South Loop at a lower cost. This month offers an enchanting charm with fewer crowds, allowing visitors to leisurely explore the neighbourhood's rich history and architecture without the hustle and bustle of peak season.
What are the top attractions in South Loop, Illinois, United States of America?
In the South Loop, visitors can discover a range of attractions that highlight the area's cultural and historical significance. The Museum Campus is a major draw, home to the Field Museum, Shedd Aquarium, and Adler Planetarium, all of which offer educational experiences and stunning views of Lake Michigan. Nearby, Grant Park provides expansive green space for relaxation and outdoor activities, while Buckingham Fountain serves as a picturesque landmark, especially when illuminated at night.Another point of interest is the historic Printers Row, known for its charming architecture and vibrant literary scene, where visitors can find quaint cafes and bookstores. The area is also close to the iconic Willis Tower, which features an observation deck offering panoramic views of the city skyline. For those interested in sports, the South Loop is within reach of both the United Centre and Guaranteed Rate Field, home to the Chicago Bulls and White Sox, respectively.
Are all fees included in the South Loop holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any South Loop holiday homes with parking?
Bookabach offers a wide selection of holiday homes in South Loop with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for South Loop holiday homes?
You can find great discounts on holiday homes in South Loop on Bookabach, 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.
Can I change or cancel my South Loop holiday home booking on Bookabach?
To find South Loop holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in South Loop?
A long-stay holiday home in South Loop is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a South Loop holiday home?
Book your South Loop holiday home 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 Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in South Loop?
Prices for holiday homes in South Loop 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in South Loop to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers 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, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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