Downtown Chicago vacation rentals

We found 799 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Find the perfect place for your stay in Downtown Chicago by choosing from 240 houses, 55 condos, and other vacation rentals. Whether you’re traveling with friends, family, or just with your pet, vacation rentals have the amenities you need and want for your stay, which might include air conditioning and a pool. What you'll find is a rental to meet everyone's needs, including options that are accessible or non-smoking.

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Frequently asked questions

What is the most popular type of vacation rental accommodation in Downtown Chicago?

Apartments are the most popular type of vacation rental in Downtown Chicago, according to our data. Even if you've got something a little different in mind, Vrbo has properties in many shapes and sizes. Browse our many options to find your perfect match.

How much does it cost to rent a vacation rental in Downtown Chicago?

The average price for a vacation 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 traveling. All you have to do is enter your travel dates into Vrbo 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 vacation rentals in Downtown Chicago?

With 38 vacation rentals 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, Vrbo can help you find a large group rental that fits the occasion.

Can I find two-bedroom vacation rentals in Downtown Chicago?

Pick from 153 two-bedroom rentals in Downtown Chicago. Give the kids the second room or fill it with a couple of your favorite people. There's a comfy spot for whoever's lucky enough to be coming along for the ride.

Are there vacation rentals 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 vacation homes with WiFi in Downtown Chicago. Check the "WiFi" box when searching on Vrbo and stay connected on your getaway.

How old do you have to be to rent a vacation rental in Downtown Chicago?

You'll need to check with the Downtown Chicago vacation home you want on Vrbo as the age limit varies. However, it's generally 16, 18 or 21.

How long can I rent a vacation rental in Downtown Chicago for?

The amount of time you can rent a Downtown Chicago vacation 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 vacation more convenient and enjoyable, such as kitchens and backyards. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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