The Loop holiday lettings

We found 1,128 holiday rentals — enter your dates for availability
Discover a selection of 324 apartments, 19 flats and other holiday rentals in The Loop that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include parking and a garden. At the end of the day, you'll be sure to find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

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Why visit The Loop

  • Iconic landmarks: The Loop is home to stunning architectural marvels, including historic skyscrapers and the renowned Millennium Park.
  • Cultural experiences: Visitors can explore world-class art at the Art Institute of Chicago and enjoy vibrant street performances.
  • Scenic Riverwalk: Stroll along the picturesque Chicago Riverwalk for beautiful views and a lively atmosphere.
  • Lush urban parks: Enjoy the greenery of public parks, perfect for relaxation amidst the bustling city.
  • Diverse dining options: The Loop offers a variety of restaurants and cafes, catering to all tastes and preferences.

Popular types of accommodation around The Loop

The Loop, nestled in the heart of Chicago, Illinois, is a vibrant neighbourhood brimming with iconic attractions and experiences. Visitors can immerse themselves in the cultural richness of the area, with renowned landmarks such as Millennium Park and the Art Institute of Chicago just moments away. For those seeking accommodation, The Loop offers a diverse selection of popular options, including luxury apartments, houses, and modern condos, ensuring a comfortable stay while exploring this bustling urban landscape.

  • Apartments: The most sought-after accommodation in The Loop, offering a convenient and comfortable stay with a range of amenities.
  • Houses: A popular choice for those seeking more space and privacy, perfect for families or groups.
  • Condos: These modern living spaces provide a stylish urban experience and are ideal for short stays.
  • Villas: Luxurious options that offer a touch of elegance and relaxation in the heart of the city.
  • Cottages: Quaint and charming, these provide a homely atmosphere for a peaceful retreat.**

Top attractions near The Loop

The Loop in Chicago, Illinois, is a vibrant neighbourhood perfect for family and urban-themed vacations. Visitors can explore iconic skyscrapers, enjoy the lush greenery of urban parks, and appreciate historic buildings that define the city's architectural heritage. Notable experiences include strolling along the scenic Chicago Riverwalk, which offers stunning views and a lively atmosphere. The Loop truly caters to those seeking cultural and city experiences, making it an ideal destination for all types of travellers.

  • Michigan Avenue: A bustling thoroughfare known for its vibrant city atmosphere, featuring high-end shops, iconic architecture, and a lively street scene, perfect for leisurely strolls and people-watching.
  • Navy Pier: A lively hub with stunning views of the waterfront, offering a variety of entertainment options, including rides, restaurants, and cultural events, all while fostering a friendly, urban environment.
  • Millennium Park: A stunning urban park featuring art installations, gardens, and a family-friendly atmosphere, ideal for outdoor activities, concerts, and enjoying the iconic Cloud Gate sculpture.

Things to do recommended for couples

For a romantic getaway in The Loop, enjoy a leisurely walk along the Chicago Riverwalk, followed by a delightful dinner at a rooftop restaurant with stunning skyline views. Don’t forget to catch a show at the historic Chicago Theatre for an unforgettable evening together.

Things to do recommended for families

Families exploring The Loop can delight in the wonders of the Field Museum, featuring fascinating dinosaur exhibits, and take a leisurely stroll through Millennium Park, where kids can splash in the Crown Fountain and enjoy the iconic Cloud Gate sculpture.

Things to do recommended for groups

Groups visiting The Loop can experience the vibrant art scene at the Art Institute of Chicago, followed by a scenic walk along the Chicago Riverwalk. Don't miss a guided architectural boat tour to admire the city's stunning skyline from the water.

*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 The Loop

If you're travelling with a group, family, pets, or planning for an extended stay, it's important to filter your options according to your specific needs. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to The Loop with a group: Think about how many bedrooms you require, as well as additional features like a fully-equipped kitchen or outdoor space for group gatherings. Luckily, you can easily refine your search for all of these options and more on Vrbo.
  • Traveling to The Loop with young kids: Travelling with young children can present its own set of challenges. It's essential to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to take into account how close you are to attractions that are suitable for families.
  • Taking your pets with you to The Loop: For many, a family holiday wouldn’t be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting The Loop: If you're in search of holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding options like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near The Loop

The Loop, Chicago, is a vibrant neighbourhood that offers a delightful blend of urban experiences and family-friendly attractions. Stroll through its bustling streets to discover iconic landmarks, stunning architecture, and lush public parks. Enjoy a variety of dining options and immerse yourself in the local culture, all within easy walking distance. Whether you're exploring art galleries or indulging in shopping, The Loop provides an unforgettable urban adventure for every traveller.

  • Chicago: As a bustling metropolis, Chicago is a vibrant city that offers a plethora of experiences for visitors. The Loop, its central business district, is surrounded by a dynamic urban landscape. Travellers flock to Chicago for its family-friendly attractions, outdoor activities, and rich city-themed experiences. Notable venues include shopping areas, arena entertainment facilities, and theatres. In close proximity, you can explore iconic landmarks such as sports stadiums, tourist precincts, and sprawling urban parks, making it an ideal base for your adventure.
  • Downtown Chicago: Located a mere 805m from The Loop, Downtown Chicago is a lively neighbourhood that captures the essence of city life. Visitors are drawn here for family outings, outdoor pursuits, and engaging city-themed activities. The area boasts an array of shopping venues, entertainment arenas, and theatres, ensuring there's something for everyone. Key attractions nearby include tourist precincts, sports stadiums, and urban parks, all contributing to a vibrant atmosphere that invites exploration and enjoyment.
  • Magnificent Mile: Situated 1km from The Loop, the Magnificent Mile is renowned for its upscale shopping and cultural offerings. This iconic stretch is a paradise for families and those seeking outdoor enjoyment amidst a city environment. Popular activities include shopping, educational experiences, and visiting entertainment arenas. The area is home to notable landmarks like tourist precincts, sports facilities, and urban parks, making it a must-visit destination for anyone looking to savour the best of Chicago.

Best time to go to The Loop

If you're planning a trip to The Loop, 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 November to January 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 CloudySlightly LowSlightly 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 SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new journeys, pick up right where you paused, or manage your existing arrangements. You can easily access the properties you’ve saved or booked by checking the sections for Potential, Upcoming, or Current Trips. To make the most of your Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in The Loop?
In The Loop, apartments are the predominant choice for holiday rentals, with around 32 available throughout this vibrant area. These apartments are often well-equipped, featuring modern kitchens, comfortable living spaces, and convenient amenities such as Wi-Fi and laundry facilities. Many are located near key attractions like Millennium Park, the Art Institute of Chicago, and various dining options, providing easy access to the city's cultural and recreational offerings.
Are there any beach house rentals in The Loop?
In The Loop, there are several beach house rentals available, offering a unique urban experience near the waterfront. While this area is more known for its towering skyline and vibrant city life, some rentals provide amenities that make them suitable for a relaxing getaway. Guests can expect properties with modern interiors, fully equipped kitchens, and spacious living areas designed for comfort after a day of exploring. Some rentals may also feature outdoor terraces or balconies, allowing visitors to enjoy views of the city or the nearby water.
How much does it cost to rent a holiday home in The Loop?
Prices for holiday rentals in The 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 traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in The Loop 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 The Loop holiday house rentals?
You can find great discounts on house rentals in The Loop 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 The Loop?
In The Loop, Illinois, popular holiday rental amenities include fully equipped kitchens, allowing guests to prepare meals at their convenience. Many rentals also feature coffee and tea makers, ensuring that you can enjoy your morning beverage in the comfort of your accommodation. For those who like to stay active, fitness facilities are commonly available, providing options for exercise during your stay. Additionally, many properties offer dedicated office spaces, suiting business travellers or anyone needing a quiet area to work. For families, some rentals also provide travel cribs, making it easier for parents travelling with young children.
Can I find family house rentals in The Loop?
In The Loop, Illinois, there are several family-friendly house rentals available, making it an excellent choice for those travelling with children. This vibrant area is surrounded by attractions such as Millennium Park, where families can enjoy outdoor concerts and the iconic Cloud Gate sculpture, commonly known as "The Bean."Many of the homes in this locale feature spacious living areas, fully equipped kitchens for preparing family meals, and multiple bedrooms to accommodate everyone comfortably. Some properties even boast amenities like private balconies with city views and laundry facilities, enhancing the convenience for families during their stay.Visitors can also take advantage of nearby cultural gems, such as the Art Institute of Chicago and the Field Museum, ensuring a blend of relaxation and exploration.
Can I rent a holiday home with a pool or hot tub in The Loop?
In The Loop, Illinois, there are several holiday homes available for rent that come equipped with pools or hot tubs. This bustling area in downtown Chicago offers a mix of modern amenities and urban charm. Many of the properties feature luxurious private pools, hot tubs, and spacious outdoor terraces, great for relaxing after exploring the city.Travellers can expect amenities such as fully equipped kitchens, stylish living areas, and sometimes even fitness facilities, making these rentals suitable for both families and groups.
Are there any The Loop holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in The 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 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 holiday rentals in The Loop?
In The Loop, there are several pet-friendly holiday rentals available for those looking to explore Chicago with their furry companions. This vibrant area is known for its stunning architecture, cultural attractions, and proximity to parks. Many of the holiday rentals come equipped with modern amenities such as fully equipped kitchens, Wi-Fi, and spacious living areas, ensuring a comfortable stay for both pets and their owners.While The Loop itself is more urban, nearby parks like Grant Park and Millennium Park provide excellent spaces for dog walkers and outdoor enthusiasts. These parks feature ample green spaces, walking paths, and beautiful gardens, allowing for enjoyable outings with pets.
Can I find long-stay holiday rentals in The Loop?
A long-stay holiday rental in The 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit The Loop for a holiday rental?
The peak season for holiday rentals in The Loop, Illinois, is from May to July, with July being the most popular month. During this vibrant period, the area comes alive with an array of events, festivals, and outdoor activities. The warm summer temperatures, typically ranging from 20 to 30 degrees Celsius, create an inclusive setting for sightseeing, dining, and exploring the rich cultural offerings of the city.Visitors can enjoy leisurely strolls along the scenic waterfront, take in the stunning architecture, or indulge in the various food festivals that showcase the diverse culinary scene. The Loop's proximity to attractions like Millennium Park and the Art Institute makes it an ideal base for those seeking both adventure and convenience.For those looking to save a bit while still enjoying the city, consider planning your visit in December. While this month falls into the low season, it presents a unique charm with festive holiday decorations, winter markets, and a quieter ambience. Plus, you'll have the opportunity to experience the local culture without the hustle and bustle of peak tourist times.Ultimately, your choice of when to visit The Loop will depend on whether you're drawn to the lively summer energy of the peak season or the peaceful and festive atmosphere of winter.
Are there any remote work holiday rentals in The Loop?
In The Loop, Illinois, there are numerous remote work-friendly holiday rentals available, with around 32 options to choose from. This vibrant area, known for its bustling atmosphere and proximity to iconic landmarks, offers accommodations that cater specifically to those working remotely. Many of these rentals provide essential amenities such as high-speed internet and dedicated office spaces, ensuring a productive work environment.Travellers can expect comfortable living areas, well-equipped kitchens, and sometimes additional features like quiet nooks or workstations, superb for balancing work and leisure. The Loop is also home to a number of cafes and co-working spaces, providing further options for a change of scenery while working. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a The Loop holiday rental?
Book your The Loop holiday 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 holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in The Loop, Illinois, United States of America?
In The Loop, visitors can explore some of Chicago's most iconic attractions. Millennium Park is a must-visit, featuring the famous Cloud Gate sculpture, also known as "The Bean," as well as beautifully landscaped gardens and outdoor concert venues. Just a short stroll away, the Art Institute of Chicago houses an extensive collection of artworks and is a key highlight for art enthusiasts.The historic Chicago Theatre, located nearby, offers a glimpse into the city's rich cultural history and often hosts live performances. For shopping and dining, State Street is a bustling area with a variety of shops and restaurants, providing an excellent urban experience.The Loop is also home to the Willis Tower (formerly Sears Tower), where visitors can take in breathtaking views of the city from the Skydeck.
Can I change or cancel my The Loop home rental booking on Vrbo?
To find The Loop holiday 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 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 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, Vrbo 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 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 The Loop holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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