The Loop holiday rentals

We found 1,148 holiday rentals — enter your dates for availability
Discover a selection of 330 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 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 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 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 home accommodation in The Loop?
Based on our research, apartments are the most in-demand type of holiday home in The Loop. But naturally, everyone's idea of an awesome stay can differ. Stayz has holiday homes in a variety of shapes and sizes, so you're sure to discover the perfect fit.
How much does it cost to rent a holiday home in The Loop?
Several factors influence what you'll pay for your holiday home in The Loop, including the season, length of stay and type of property. Still, all our holiday homes have one thing in common — exceptional value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in The Loop?
Prices for beach houses in The Loop will vary depending on the size and type of the property and when you're travelling. Just enter your travel dates into Stayz and the number of guests to see your options and prices. From there you can use our filters to narrow your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in The Loop?
With 206 properties that welcome pets, your furry friend can join in the fun on your The Loop holiday. Use our filter tool to browse our pet-friendly holiday homes and find your pawfect holiday home on Stayz.
Can I rent a house with a pool in The Loop?
Pack your swimming gear and goggles, because there are 86 houses with a private pool in The Loop. Stay at one of these popular holiday homes and every day can be a pool day. Simply enter your travel dates into Stayz, then use the "pool" filter to find a place to make a splash!
What are popular home amenities in The Loop?
The most popular home amenities people are looking for in The Loop are a barbecue grill, a lake view and a garden. Whether you're taking a trip with friends, family or even pets, Stayz holiday properties come with the best amenities for hanging out with the people you cherish the most.
Are there large group holiday homes in The Loop?
The Loop has three holiday homes that can cater to 10 or more people. These properties come with the space you need to share good times with family and friends.
Are there holiday homes in The Loop that welcome kids?
Gather your whole family for a fun-packed adventure in The Loop at one of our 206 family-friendly properties. These stays feature conveniences that are ideal for getaways with the little ones, like laundry facilities, multiple bedrooms and outdoor spaces. Simply click on the "Properties good for families" filter box and pick your favourite.
What are the top attractions for families in The Loop?
Keep the kids busy at these popular family-friendly attractions in The Loop:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in The Loop?
Yes, The Loop has 112 one-bedroom homes available. Often located in sought-after areas because of their compact size, a one-bedroom home is great if you're travelling with your partner or a friend. And with comforts such as air conditioning and more privacy than a standard hotel, you'll be able to chill out while enjoying this amazing destination.
Can I find two-bedroom holiday homes in The Loop?
The Loop has 41 two-bedroom properties for you to pick from. Experience a holiday home with all the comfort and space you're looking for at a price that's hard to resist on Stayz.
Are there holiday homes with WiFi in The Loop?
The Loop has 18 holiday homes with WiFi, so you can stay connected while you're on holiday. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movie blockbusters to checking emails, these Stayz homes make it a breeze to get online.
How can I find holiday homes with air conditioning in The Loop?
Work out your travel dates and then use our filters to look for holiday homes with ac in The Loop on Stayz. With 205 air-conditioned properties to choose from here, you can look forward to a comfy and cool stay.
How old do you have to be to rent a holiday home in The Loop?
The minimum required age is generally 16, 18 or 21. It can differ from one property to another on Stayz, so check the rules of your preferred The Loop holiday home before making a booking.
How long can I rent a holiday home in The Loop for?
The length of time you can book a holiday home in The Loop depends on the property. Just enter your selected travel dates to look at a list of options offering extended stays. With lots of amenities such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover someplace just right to call your home away from home in The Loop.

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