The Loop holiday homes

We found 1,105 holiday rentals — enter your dates for availability
Discover a selection of 319 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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    Enjoy full kitchens, laundry, pools, gardens and more

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Why visit The Loop

  • Iconic Skyscrapers: Marvel at the stunning architecture of Chicago’s tallest buildings, which define The Loop's skyline.
  • Chicago Riverwalk: Enjoy a scenic stroll along the Riverwalk, where you can take in the views and vibrant atmosphere.
  • Cultural Attractions: Explore the rich cultural scene with various museums, galleries, and public art installations.
  • Urban Parks: Relax in the picturesque parks scattered throughout The Loop, perfect for families and city lovers alike.
  • Historic Landmarks: Discover the history of Chicago through its well-preserved historic buildings and landmarks.

Top attractions near The Loop

The Loop in Chicago offers a vibrant urban experience perfect for families and city lovers. Explore iconic skyscrapers, historic buildings, and urban parks while soaking in the bustling cityscape. Don’t miss the picturesque Chicago Riverwalk for a leisurely stroll. Enjoy the rich culture and lively atmosphere that makes The Loop a must-visit destination for an unforgettable holiday.

  • Navy Pier: A vibrant waterfront destination featuring entertainment, dining, and stunning views of Lake Michigan. Enjoy leisurely strolls, boat tours, and cultural events in a lively atmosphere.
  • Grant Park: Often referred to as Chicago's Front Yard, this expansive urban park is perfect for family outings, with beautiful gardens, walking paths, and iconic monuments.
  • 875 North Michigan Avenue: A striking skyscraper offering breathtaking city views from its observation deck, showcasing Chicago’s architectural beauty and urban landscape.

Things to do recommended for couples

Discover the charm of The Loop with a leisurely walk along the Riverwalk, followed by a romantic dinner at a rooftop restaurant. Don't miss a stunning sunset view from the Willis Tower Skydeck, creating unforgettable memories together in the heart of Chicago.

Things to do recommended for families

Your family will love exploring Millennium Park, where kids can splash around in the Crown Fountain and take photos with the iconic Cloud Gate sculpture. Don't miss the Art Institute of Chicago, offering engaging exhibits for all ages, and the nearby Chicago Riverwalk for a scenic stroll.

Things to do recommended for groups

Groups visiting The Loop in Chicago can take a guided architectural boat tour along the Chicago River to admire the city's iconic skyline and enjoy a group outing to Millennium Park, where you can snap photos at the famous Cloud Gate sculpture.

*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

Whether you're travelling with a group, as a family, bringing along your pets, or seeking extended stays, be sure to filter by the appropriate priorities. Here are some Vrbo booking tips for you.

  • Traveling to The Loop with a group: Think about how many bedrooms you’ll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Luckily, you can easily apply filters for all of these options and more on Vrbo.
  • Traveling to The Loop with young kids: Travelling with young kids can be quite a task. 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: Some families wouldn’t consider their journey complete without their furry mate joining in. If that’s you, have a look at Vrbo listings that welcome pets. Many of these pet-friendly homes even come with feeding bowls and beds to make sure everyone feels right at home.
  • Planning for a long term stay visiting The Loop: If you're searching for holiday rentals with 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 monthly rental options. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near The Loop

Exploring The Loop in Chicago promises a vibrant urban adventure filled with iconic attractions and landmarks. This bustling neighbourhood offers everything from stunning skyscrapers and public art installations to picturesque parks and family-friendly activities. Stroll through the heart of downtown, take in the stunning architecture, and enjoy the lively atmosphere that makes The Loop a must-visit destination for any traveller. With everything within walking distance, you're sure to create unforgettable memories in this dynamic city hub.

  • Chicago: Chicago is a vibrant city that encompasses the iconic Loop neighbourhood, offering an exciting urban experience with a mix of family-friendly attractions and outdoor adventures. You can immerse yourself in diverse activities, including exploring bustling shopping areas, catching live shows at arenas or theatres, and enjoying the city's landmark sports stadium, tourist precincts, and urban parks. The city’s dynamic blend of cultural attractions and modern amenities makes it a perfect destination for travellers looking for a rich city-themed experience.
  • Downtown Chicago: Downtown Chicago is a lively neighbourhood situated just 805m from the Loop. This area is celebrated for its family-oriented, outdoor, and city-themed attractions. Here, visitors can enjoy a variety of activities from exploring shopping areas to attending events at arena entertainment facilities and theatres. The neighbourhood is also home to notable landmarks like a tourist precinct, sports stadium, and urban park, ensuring a memorable and varied travel experience for those keen to delve into the heart of Chicago's urban charm.
  • Magnificent Mile: Magnificent Mile, located 1km from the Loop, is a bustling neighbourhood known for its family, outdoor, and city-themed attractions. It offers an array of appealing activities, including shopping, educational experiences, and entertainment at arena facilities. With close proximity to a tourist precinct, sports stadium, and urban park, Magnificent Mile provides an enticing blend of urban sophistication and leisure opportunities, ideal for travellers eager to explore a different facet of Chicago’s vibrant culture.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudySlightly High
April46.0°F (7.8°C)Light RainMostly SunnySlightly High
May57.0°F (13.9°C)Light RainMostly SunnyAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverage
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 SunnyAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudySlightly Low

Booking with Vrbo is simple

Looking to save on your next adventure? If you can be flexible with your travel dates, you'll benefit from fluctuating prices. Plus, booking a longer stay often leads to significant savings. To find the perfect Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a dedicated space where you can start planning new trips, continue with current plans, or review and organise your bookings. Any properties you’ve saved or reserved are neatly categorised as Potential, Upcoming, or Current Trips. For more details on using Trip Boards, please visit: https://www.bookabach.co.nz/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.
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.
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.
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 Bookabach.
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.
Are all fees included in the The 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 The Loop holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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 The Loop holiday homes?
You can find great discounts on holiday homes in The 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 The Loop holiday home booking on Bookabach?
To find The 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 The Loop?
A long-stay holiday home 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 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 The Loop holiday home?
Book your The 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 The Loop?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in The 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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