The Loop holiday lettings

We found 1,309 holiday rentals — enter your dates for availability

Select from 62 houses, 255 apartments and other holiday rentals to find the perfect place for your stay in The Loop. 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.

Holiday rentals with weekly discounts - The Loop

Showing deals for:3 Oct - 10 Oct
  • 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, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

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.

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.

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

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.

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 accommodation in The Loop?
Based on our research, apartments are the most in-demand type of holiday rental in The Loop. But naturally, everyone's idea of an awesome stay can differ. Vrbo has holiday rentals 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 rental in The Loop?
Several factors influence what you'll pay for your holiday rental 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 Vrbo 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 rentals 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 rentals and find your pawfect holiday home on Vrbo.
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 rentals and every day can be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find a place to make a splash!
What are popular rental amenities in The Loop?
The most popular rental 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, Vrbo holiday properties come with the best amenities for hanging out with the people you cherish the most.
Are there large group holiday rentals 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 rentals 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 rentals in The Loop?
Yes, The Loop has 112 one-bedroom rentals available. Often located in sought-after areas because of their compact size, a one-bedroom rental 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 rentals 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 Vrbo.
Are there holiday rentals with WiFi in The Loop?
The Loop has 18 holiday rentals 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 Vrbo homes make it a breeze to get online.
How can I find holiday rentals with air conditioning in The Loop?
Work out your travel dates and then use our filters to look for holiday rentals with ac in The Loop on Vrbo. 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 rental in The Loop?
The minimum required age is generally 16, 18 or 21. It can differ from one property to another on Vrbo, so check the rules of your preferred The Loop holiday rental before making a booking.
How long can I rent a holiday rental in The Loop for?
The length of time you can book a holiday rental 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.

More Holiday Rentals ideas

People also search for