Downtown Chicago holiday homes

We found 782 holiday rentals — enter your dates for availability

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September 2025

October 2025

Discover a selection of 931 apartments, 60 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.

Holiday rentals with weekly discounts - Downtown Chicago

Showing deals for:12 Dec - 19 Dec

Exceptional

(21 reviews)

Beautiful Downtown 3BR with Free Parking

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$955 per night

includes taxes & fees

The apartment is flooded with beautiful light from multiple sides

Exceptional

(55 reviews)

Chic Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$788 per night

includes taxes & fees

Spacious living room and kitchen filled with light throughout the day

Exceptional

(59 reviews)

Beautiful Corner 2 Bedroom in the Loop | Roof Deck

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$822 per night

includes taxes & fees

Exceptional

(60 reviews)

Stylish Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$753 per night

includes taxes & fees

The open living room and dining area is flooded with light during the day

Exceptional

(18 reviews)

Splendid Corner 3BR in the Loop | City Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$980 per night

includes taxes & fees

Wonderful

(26 reviews)

Spectacular Corner 3BR in the Loop | City Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$1,003 per night

includes taxes & fees

Exceptional

(44 reviews)

Stunning Corner 2BR in the Loop | City & Lake Views

Chicago, IL

7% off

for 7 nights, 1 apartment

NZ$758 per night

includes taxes & fees

Find spaces that suit your style

Find properties near top attractions in Downtown Chicago

Michigan Avenue

Find the best place to stay - Downtown Chicago

Vacation Starts Here! Near Chicago Riverwalk and The River Theater, Pets Allowed

Sleeps 4 · 1 bedroom · 1 bathroom

Delightful Room w/ Whimsical Decor & Modern Amenities Near Magnificent Mile

Sleeps 2 · 1 bedroom · 1 bathroom

Best Place to Stay in Chicago! Relaxing Unit w/ City View, Pets Allowed!

Sleeps 2 · 1 bedroom · 1 bathroom

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, Bookabach 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 Bookabach 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, Bookabach 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 Bookabach 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 Bookabach 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.