The Loop holiday homes

We found 1,144 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.

Find spaces that suit your style

  • Peace of mind

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  • 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 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 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. Bookabach 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 Bookabach 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 Bookabach.
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 Bookabach, 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, Bookabach 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 Bookabach.
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 Bookabach 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 Bookabach. 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 Bookabach, 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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