The Loop holiday rentals

We found holiday rentals — enter your dates for availability

Select from 58 houses, 249 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:25 Jul - 1 Aug

Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Living area
10 out of 10 rating
Exceptional
(20 reviews)

Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Chicago, IL

8% off
Price is S$51,687
S$7,384 per night
includes taxes & fees
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!

Find spaces that suit your style

  • 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

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.

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