A river with yellow boats, a bridge, and tall buildings.

The Loop holiday rentals

We found 1,131 holiday rentals — enter your dates for availability

Discover a selection of 320 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.

Find spaces that suit your style

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Find properties near top attractions in The Loop

A large metallic sphere sculpture in a public square surrounded by tall buildings.

Millennium Park

A cityscape at night with illuminated buildings, a river, and a bridge.

Chicago Riverwalk

A city skyline with tall skyscrapers, a river, and a bridge.

Willis Tower

A grand staircase in a historic building with classical architecture, including columns and ornate railings.

Art Institute of Chicago

A large illuminated sign with the letters "CHICA" and a circular design.

Chicago Theatre

A cityscape with a prominent modern sculpture in the foreground and a mix of historic and contemporary buildings in the background.

Cloud Gate

A city skyline with illuminated skyscrapers and a fountain with water jets.

Buckingham Fountain

A large, classical building with tall columns and large windows.

Chicago City Hall

A grand hall with a high, ornate ceiling and intricate architectural details.

Chicago Cultural Center

A theater entrance with a marquee reading "Hamilton" and an "EXIT" sign above the door.

CIBC Theatre

Find the best place to stay - The Loop

Sentral Michigan Avenue

Sleeps 2 · 1 bedroom

Kasa Lake Shore Chicago

Sleeps 2 · 1 bedroom · 1 bathroom

Kasa South Loop Chicago

Sleeps 3 · 1 bedroom · 1 bathroom

Kasa Magnificent Mile Chicago

Sleeps 2 · 1 bedroom · 1 bathroom

Level Chicago – Old Town

Premier Host

LIVN Millennium Park Downtown Chicago 2BR

Sleeps 4 · 2 bedrooms · 1 bathroom

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
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 The Loop

Iconic landmarks: The Loop is home to stunning skyscrapers and historic buildings, showcasing Chicago's unique architectural heritage.
Millennium Park: A must-visit urban park featuring beautiful green spaces, public art, and the famous Cloud Gate sculpture.
Cultural experiences: Explore renowned institutions like the Art Institute of Chicago, offering extensive art collections and exhibitions.
Chicago Riverwalk: Enjoy leisurely strolls along the scenic waterfront, lined with dining and entertainment options.
Vibrant atmosphere: The Loop buzzes with energy, providing a lively environment perfect for families and urban explorers.

Popular types of accommodation around The Loop

Welcome to The Loop, Chicago's vibrant heart, where stunning architecture meets a wealth of cultural experiences. Explore the city's iconic landmarks, from Millennium Park to the Art Institute of Chicago, all within walking distance. The Loop offers a variety of holiday rentals, including studio apartments, spacious one-bedroom flats, and modern condos, perfect for your stay. Enjoy the convenience and excitement of this dynamic neighbourhood while finding the ideal accommodation for your getaway.

Apartments: The top choice, these cosy urban flats offer vibrant living spaces perfect for exploring The Loop.
Private Holiday Homes: Stylish standalone residences provide a homely retreat in the heart of the city.
Condos: Contemporary, secure living spaces that blend comfort with modern design.
Villas: Elegant, spacious dwellings ideal for a luxurious city escape.
Cottages: Quaint, characterful abodes offering a charming stay amidst urban surroundings.**

Top attractions near The Loop

The Loop, Chicago, is an exciting urban neighbourhood perfect for families and city-themed holidays. Visitors can explore iconic skyscrapers, beautiful urban parks, and historic buildings, all rich in culture and experience. This vibrant area offers a plethora of attractions that cater to various interests, making it an ideal destination for those seeking a lively city atmosphere and memorable family experiences.

Michigan Avenue: Experience bustling city vibes along this storied thoroughfare, renowned for its vibrant urban atmosphere and excellent local shopping opportunities, all situated near The Loop.
Navy Pier: Enjoy a scenic urban jetty atmosphere with friendly local ambience, offering picturesque views and leisurely strolls close to The Loop.
Millennium Park: Delight in family-friendly outdoor spaces in this urban park, perfect for leisurely picnics and enjoying the city's dynamic energy near The Loop.

Things to do recommended for couples

For a romantic getaway in The Loop, explore the serene Millennium Park, take a scenic boat tour along the Chicago River, and enjoy a candlelit dinner at a rooftop restaurant with stunning skyline views. Don't forget to catch a show at the historic Chicago Theatre for a memorable evening.

Things to do recommended for families

Families visiting The Loop in Chicago can have a fantastic time at the Shedd Aquarium, where kids can marvel at marine life, and enjoy the interactive exhibits at the Field Museum, filled with fascinating artefacts and engaging activities.

Things to do recommended for groups

Explore the vibrant Art Institute of Chicago for world-class artworks or take a scenic architecture boat tour along the Chicago River. For a unique experience, enjoy a group outing at the famous Chicago Magic Lounge for an evening of illusions and entertainment.

*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

When travelling with a group, family, pets, or seeking extended stays, it's essential to filter according to your specific priorities. Here are some helpful booking tips for Stayz.

Traveling to The Loop with a group: Consider the number of bedrooms you require, as well as features like a fully-equipped kitchen or an outdoor area suitable for group gatherings. Fortunately, you can filter for all these options—and more—on Stayz.
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, as well as ensure that suitable amenities, like a private swimming pool, are available. Additionally, it's wise to think about your closeness to attractions that cater to families.
Taking your pets with you to The Loop: For many, a family holiday simply isn’t complete without their furry companion. If this resonates with you, then have a look at Stayz properties that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels right at home.
Planning for a long term stay visiting The Loop: If you are seeking holiday lets with discounts for extended stays of a month or more, you have come to the right place. By using the appropriate filter, you can effortlessly find and secure savings on monthly lets. You might also want to include extras such as a parking space, a well-appointed kitchen, or a private pool in your search.

Where to stay near The Loop

The Loop in Chicago is a vibrant urban hub perfect for families and outdoor enthusiasts alike. Visitors can immerse themselves in a blend of stunning architecture, renowned theatres, and lush parks. Explore the iconic Millennium Park, marvel at the Art Institute of Chicago, or take a leisurely stroll along the Chicago Riverwalk. With its lively atmosphere and friendly locals, The Loop offers an unforgettable city experience filled with culture and entertainment.

Chicago: As a vibrant metropolis, Chicago is the birthplace of The Loop, its bustling central business district. This city draws travellers seeking family-friendly activities, outdoor adventures, and urban experiences. Visitors can explore a myriad of shopping areas, enjoy thrilling arena entertainment, and indulge in world-class theatre. Notable landmarks nearby include iconic sports facilities, lively tourist precincts, and picturesque urban parks, making it a hub of activity and culture.
Downtown Chicago: Located a mere 805m from The Loop, Downtown Chicago is a dynamic neighbourhood where visitors can immerse themselves in family-oriented attractions and outdoor spaces. This area offers a delightful array of shopping districts, vibrant arena entertainment, and captivating theatre performances. Nearby, you'll find significant local landmarks including tourist precincts, sports facilities, and lush urban parks, all contributing to a lively atmosphere that beckons exploration.
Magnificent Mile: Situated 1km away from The Loop, the Magnificent Mile is a renowned neighbourhood famed for its upscale shopping and cultural offerings. Visitors flock here for family-friendly activities, outdoor enjoyment, and an exciting urban vibe. The area boasts numerous shopping venues, educational attractions, and engaging arena entertainment. With landmarks like tourist precincts, sports facilities, and beautiful urban parks nearby, the Magnificent Mile promises a memorable experience for all who visit.

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 Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Slightly High	Slightly Low
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Average	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Average	Slightly High
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Average
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Average
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Slightly Low	Average

Booking with Stayz is simple

Looking to cut costs on your upcoming holiday? Being flexible with your travel dates can make a difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Stayz property that suits your budget, simply use our filters to sort by price, location, and type of holiday rental.

Stayz Trips: Effortless planning

Stayz's innovative Trip Board offers you a dedicated space to design new journeys, pick up right where you left off, or review and organise your plans. Properties you have previously saved and booked are now neatly categorised as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.stayz.com.au/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 Stayz.

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 Stayz?

Stayz 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?

Stayz 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 Stayz, 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 Stayz?

To find The Loop holiday rentals with free cancellation, just use Stayz'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, Stayz 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 Stayz?

Stayz'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 Stayz 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. Stayz offers something for every taste and budget, from affordable homes in The Loop to more spacious homes.

What can I expect from Stayz customer service and StayzCare™ support?

Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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 StayzCare™ and how does it work?

Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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 Stayz as a host?

Joining Stayz 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, Stayz 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 Stayz 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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