Downtown Chicago holiday rentals

We found 802 holiday rentals — enter your dates for availability

Discover a selection of 1002 apartments, 61 flats and other holiday rentals in Downtown Chicago that are perfect for your trip. Whether you’re travelling with friends, family or just with your pet, holiday rentals have the amenities that you need and want for your stay, which might include parking and a pool. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

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 Downtown Chicago?
Apartments are the most popular type of holiday home in Downtown Chicago, according to our data. Even if you've got something a little different in mind, Stayz has properties in many shapes and sizes. Browse our many options to find your perfect match.
How much does it cost to rent a holiday home in Downtown Chicago?
The average price for a holiday home in Downtown Chicago can vary depending on factors such as time of year, length of stay and property type. Whether you're in search of a villa with space for extended family or a comfy cabin for just you and your sweetheart, just enter your dates of travel to find stays with amazing value.
How much does it cost to rent a beach house in Downtown Chicago?
Prices for beach houses in Downtown Chicago differ depending on the type and size of the property and when you're travelling. All you have to do is enter your travel dates into Stayz and the number of guests to see available options and prices. From there you can use our filter tool to narrow your search results by ratings, amenities and more.
Are there large group holiday homes in Downtown Chicago?
With 38 holiday homes that can host 10 or more people in Downtown Chicago, you won't have to cross anyone off the invite list. From family get-togethers to special events like birthday parties and weddings, Stayz can help you find a large group home that fits the occasion.
Can I find two-bedroom holiday homes in Downtown Chicago?
Pick from 153 two-bedroom homes in Downtown Chicago. Give the kids the second room or fill it with a couple of your favourite people. There's a comfy spot for whoever's lucky enough to be coming along for the ride.
Are there holiday homes with WiFi in Downtown Chicago?
Whether you'd like to stay in touch with world events, look over emails or surf social media, there are 84 holiday homes with WiFi in Downtown Chicago. Check the "WiFi" box when searching on Stayz and stay connected on your getaway.
How old do you have to be to rent a holiday home in Downtown Chicago?
You'll need to check with the Downtown Chicago holiday home you want on Stayz as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Downtown Chicago for?
The amount of time you can rent a Downtown Chicago holiday home for depends on the property. Simply put in your travel dates to browse options that offer long-term stays. They have the things you need to make your extended holiday more convenient and enjoyable, such as kitchens and backyards. Some holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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