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Heart of Chicago holiday rentals

We found 51 holiday rentals — enter your dates for availability

Discover a selection of 5 homes and other holiday rentals in Heart of Chicago that are perfect for your trip. Holiday rentals offer the amenities that you expect for you and your friends, family or even pets, such as cable TV and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.

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 home accommodation in Heart of Chicago?
According to our data, apartments are the most popular holiday property type in Heart of Chicago. But as you'd expect, everyone's idea of an epic trip can vary. Stayz has holiday homes in a variety of sizes and shapes, so you're bound to find your ideal fit.
How much does it cost to rent a holiday home in Heart of Chicago?
Different factors determine how much you'll pay for a holiday home in Heart of Chicago, including the time of year, property type and length of stay. However, all Stayz homes have something in common — incredible value. Just add your travel dates to find your ideal match.
How much does it cost to rent a beach house in Heart of Chicago?
Prices for beach houses in Heart of Chicago vary depending on the type and size of the property and time of year you're travelling. Simply enter your travel dates into Stayz and the number of guests to see available options and prices. From there you can use our filters to narrow down your search by ratings, nearby activities and more.
Are there pet-friendly holiday homes in Heart of Chicago?
You're in luck! There are. You can pick from nine holiday homes that cater to pets in Heart of Chicago. Many of our pet-friendly holiday homes even come with an outdoor area for your furry pal to have fun in, special dog beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find a pad that'll set tails wagging on Stayz.
What are popular home amenities in Heart of Chicago?
When it comes to home amenities that guests are on the lookout for in Heart of Chicago, a firepit, nearby museums and a garden are the most popular. With Stayz holiday homes, you'll find options to fit your style and taste, whether you're going away with family members, friends or even pets.
Are there large group holiday homes in Heart of Chicago?
Yes, you can choose one of two holiday homes in Heart of Chicago that can host a group of five or more guests. From family get-togethers to events like a friend's birthday, these stays have enough space to hang out with the people that matter the most.
Are there holiday homes in Heart of Chicago that welcome kids?
Heart of Chicago has nine family-friendly holiday homes to pick from. And booking a stay that welcomes youngsters is easy with our "Properties good for families" filter. As well as having the whole place to yourselves, you'll have access to amenities and perks like extra bedrooms, private pools and yards.
What are the top attractions for families in Heart of Chicago?
Keep the kids occupied at these popular family-friendly attractions in Heart of Chicago:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Can I find two-bedroom holiday homes in Heart of Chicago?
Gather your loved ones and enjoy a relaxing escape in one of the eight two-bedroom holiday properties Heart of Chicago has to offer.
Are there holiday homes with WiFi in Heart of Chicago?
You'll have a choice of eight holiday homes with WiFi in Heart of Chicago. If you'd like to disconnect from daily life during your trip, but still need to be connected to the internet, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Heart of Chicago?
You can choose from nine Stayz holiday homes with air conditioning in Heart of Chicago providing that gentle, cool breeze and extra element of comfort. Simply enter your preferred travel dates and then use our handy filters to look for stays with air conditioning.
How old do you have to be to rent a holiday home in Heart of Chicago?
The minimum required age is typically 16, 18 or 21. It can vary from property to property on Stayz, so look at the rules of your chosen Heart of Chicago holiday home before booking your stay.
How long can I rent a holiday home in Heart of Chicago for?
The length of time you can rent a holiday home in Heart of Chicago depends on the property. Simply enter your chosen dates to see a list of options offering extended stays. With plenty of creature comforts like kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover a perfect place to call your home away from home in Heart of Chicago.

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