The Loop holiday lettings

We found 1,168 holiday rentals — enter your dates for availability

Discover a selection of 366 apartments, 20 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 Architecture: Marvel at the impressive skyscrapers and historic buildings that define Chicago's skyline.
  • Urban Parks: Enjoy the green spaces and delightful parks, perfect for family outings and relaxation.
  • Chicago Riverwalk: Stroll along the scenic Riverwalk, offering picturesque views and vibrant local culture.
  • Cultural Attractions: Explore numerous museums and galleries that showcase the city's rich history and art scene.
  • Varied Accommodation: Choose from stylish apartments and modern condos that cater to every traveller's needs.

Popular types of accommodation around The Loop

If you're pondering the best accommodation options in The Loop, look no further! Our most sought-after choices include stylish apartments, charming houses, and modern condos. Whether you're searching for Chicago Loop apartments, luxury apartment rentals, or a cosy flat, we offer a variety of Chicago apartments that cater to every traveller's needs. Enjoy your stay with confidence, knowing we prioritise transparency and reassurance every step of the way.

  • Apartments: The top choice for holiday rentals in The Loop, offering a variety of styles and amenities for a comfortable stay.
  • Houses: A popular option for families or groups seeking a home-like atmosphere during their visit.
  • Condos: Stylish and modern, these rentals provide a chic urban experience in the heart of The Loop.
  • Cottages: Quaint and charming, perfect for those looking for a cosy retreat within the city.
  • Villas: Luxurious accommodations that offer ample space and upscale features for a lavish getaway.**

Top attractions near The Loop

The Loop in Chicago is perfect for family-friendly, outdoor city holidays, boasting attractions like impressive skyscrapers, urban parks, and historic buildings. Visitors can immerse themselves in the local culture while exploring the Chicago Riverwalk and the numerous museums within the Loop. With a variety of experiences on offer, it's an ideal destination for those seeking a vibrant city adventure.

  • Michigan Avenue: A vibrant thoroughfare known for its bustling atmosphere, Michigan Avenue offers a mix of high-end shopping, dining, and iconic architecture. It's perfect for leisurely strolls and immersing yourself in the city's energy.
  • Navy Pier: This lively jetty features stunning waterfront views, entertainment, and attractions. With its friendly atmosphere, Navy Pier is ideal for families and friends looking to relax and enjoy the scenery.
  • Millennium Park: A beautiful urban park that showcases stunning art installations and lush green spaces. It's a fantastic spot for picnics, outdoor concerts, and enjoying the vibrant city life with family.

Things to do recommended for couples

For a delightful couple's getaway in The Loop, enjoy a lively evening at the House of Blues Chicago, just 186m away, or savour a romantic meal at the Historic Michael Jordan Restaurant, 373m away. Don't forget to catch a concert at the Aragon Ballroom, 3.7km away!

Things to do recommended for families

Families exploring The Loop in Chicago can experience the excitement of Wrigley Field, enjoy the tranquillity of the Northerly Island Natural Area, and unwind at The East Bank Club, all offering unique activities perfect for a memorable family holiday.

Things to do recommended for groups

Groups visiting The Loop in Chicago can enjoy a captivating show at the Chicago Theatre, indulge in laughter at Second City, or shop at the Chicago Place Mall for a delightful blend of city and family vibes, all within easy reach of each other.

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 seeking longer stays, be sure to filter based on your key priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to The Loop with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search to include all these options and much more on Vrbo.
  • Traveling to The Loop with young kids: Travelling with young children can present its challenges. It’s important to prioritise 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 The Loop: For many, a family holiday isn’t quite the same without their furry companion. If you can relate to this, explore the Vrbo listings that welcome pets. Many of these pet-friendly accommodations supply feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting The Loop: If you're seeking holiday rentals with offers 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 accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or even a private pool in your search criteria.

Where to stay near The Loop

The Loop in Chicago is a vibrant hub perfect for families and outdoor enthusiasts. With its urban atmosphere, visitors can explore iconic landmarks, delightful parks, and engaging neighbourhoods. From the thriving downtown to charming local spots, the area offers a blend of business and leisure. Whether strolling along the historic streets or enjoying the friendly vibe, there's an abundance of experiences waiting to be discovered in and around The Loop.

  • Chicago: Situated a mere 124m from The Loop, Chicago is a vibrant metropolis that beckons visitors with its rich cultural tapestry. Known for its family-friendly attractions and outdoor spaces, this city is perfect for those seeking a lively urban experience. Key highlights include bustling shopping areas and the renowned United Center, a premier venue for sports and entertainment. The city’s historic landmarks, such as Wrigley Field, offer a glimpse into its storied past, while the lively tourist precinct ensures there’s never a dull moment.
  • Downtown Chicago: Just 311m from The Loop, Downtown Chicago is the heart of the city, pulsating with energy and excitement. This neighbourhood is ideal for families and those who enjoy outdoor activities. Visitors can explore the myriad shopping options and catch a show at one of the many theatres. Attractions such as Millennium Park and the Art Institute of Chicago are within easy reach, offering cultural enrichment alongside the vibrant atmosphere of the bustling tourist precinct and sports facilities.
  • Magnificent Mile: Located 497m from The Loop, the Magnificent Mile is a bustling stretch of Michigan Avenue renowned for its upscale shopping and dining. This area is perfect for families and those looking for a quintessential city experience. Here, visitors can enjoy a variety of activities, from exploring high-end boutiques to immersing themselves in local education centres. Attractions like the John Hancock Center and the Chicago Riverwalk provide stunning views and memorable experiences, making it a must-visit destination.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 simple

If you're keen to save on your next holiday, think about being flexible with your travel dates, as prices can vary. Additionally, opting for a longer stay often results in significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of accommodation.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform to help you plan new journeys, manage your existing arrangements, or review your bookings. Your saved or reserved properties are neatly categorised into Potential, Upcoming, or Current Trips. To explore the Trip Boards, please 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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