Streeterville, Chicago holiday accommodation: short-term house rentals & properties

Discover a selection of 63 homes, 77 apartments and other holiday rentals in Streeterville that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Streeterville

Showing deals for:26 Sept - 3 Oct

Exceptional

(8 reviews)

3BR Luxury Modern Apartment

Chicago, Illinois

7% off

AU$1,026 per night

includes taxes & fees

Open living room and dining space with lake views and great light

Exceptional

(26 reviews)

Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

AU$832 per night

includes taxes & fees

Exceptional

(27 reviews)

Chic Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

AU$751 per night

includes taxes & fees

Exceptional

(34 reviews)

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Chicago, Illinois

7% off

AU$761 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Streeterville

Water Tower Place

Find the best place to stay - Streeterville

Showing deals for: 24 Sept - 27 Sept

Sitting Area. Exact unit will be assigned upon arrival. Views, colors and decor may vary.

Group Vacation! 2 Spacious Units Near Oak Street Beach! Onsite Parking!

Sleeps 8 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$858 per night

includes taxes & fees

Modern Corner 2BR in Streeterville | Roof Deck | Lake Views

Sleeps 6 · 2 bedrooms · 1 bathroom

for 3 nights, 1 apartment

AU$907 per night

includes taxes & fees

Making The Best Memories Along The Way! Free Breakfast, Pets Allowed

Sleeps 5 · 2 bedrooms · 1 bathroom

for 3 nights, 1 home

AU$647 per night

includes taxes & fees

Two Bedroom with 1 King Bed and 1 Queen Bed

Spacious Good-Value Accommodation! 2 Convenient Units, Free Breakfast

Sleeps 10 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,290 per night

includes taxes & fees

A Place You'll Surely Enjoy! Full Kitchen, Free Breakfast, Pets Allowed

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 home

AU$510 per night

includes taxes & fees

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 Streeterville?

Apartments are the most popular style of holiday home in Streeterville, according to our data. Even if you've got something else in mind, Stayz has holiday homes in many sizes and shapes. Explore our options to find your perfect match.

How much does it cost to rent a holiday home in Streeterville?

Property type, length of stay and season are some things that can affect the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From comfy cabins to sprawling villas, all Stayz holiday homes provide incredible value.

How much does it cost to rent a beach house in Streeterville?

Prices for beach houses in Streeterville may differ depending on the size and type of the property and when you're travelling. Simply enter your travel dates into Stayz and how many guests to view available options and prices. From there you can use the filters to narrow your search by amenities, nearby activities, ratings and more.

Are there pet-friendly holiday homes in Streeterville?

Pack a tug toy and treats for the pup in your life because Streeterville has 73 holiday homes that roll out the welcome mat to pets. Let your happy hound get in on the family fun at one of our pet-friendly holiday homes on Stayz. Simply enter your travel dates and destination, then check our "Pets allowed" filter box.

Can I rent a house with a pool in Streeterville?

Add a whole new level of fun to your adventure by booking one of the 30 houses with a private pool in Streeterville. Use our search filter to find the kind of property you want on Stayz, and then spend your days splishing and splashing in a swimming pool that's for your use only.

What are popular home amenities in Streeterville?

When it comes to home amenities that people look for in Streeterville, a garden, a nearby waterfront and nearby museums rank highest. With Stayz holiday homes, you'll enjoy choices to match your style and taste, whether you're planning to get away with friends, relatives or even pets.

Are there large group holiday homes in Streeterville?

Streeterville has three holiday homes that can cater to 10 or more guests. These stays come with the space and privacy you need to share good times with family and friends.

Are there holiday homes in Streeterville that welcome kids?

Gather your whole family for an unforgettable adventure in Streeterville at one of our 73 family-friendly holiday homes. Many of these stays come with amenities that are great for trips with children, including kitchens, living rooms and private pools. Just click on the "Properties good for families" filter box and pick your favourite option.

What are the top attractions for families in Streeterville?

Keep the kids amused at these fun family-friendly attractions in Streeterville:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

Are there one-bedroom holiday homes in Streeterville?

Take your pick from 23 one-bedroom homes in Streeterville. Whether you're looking for a cosy chalet or a fancy condo, Stayz's one-bedroom homes are just right if you don't need loads of space. One of the perks of having your own digs? You won't ever need to share your getaway with strangers.

Can I find two-bedroom holiday homes in Streeterville?

Take off with your besties and enjoy total privacy and comfort in one of the 22 two-bedroom holiday homes Streeterville has to offer.

Are there holiday homes with WiFi in Streeterville?

Streeterville has 12 holiday homes with WiFi, so you'll be able to stay connected while travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to posting pics on social media, these Stayz homes will keep you online.

How can I find holiday homes with air conditioning in Streeterville?

Streeterville has 73 holiday homes where you can relax and recharge in air-conditioned comfort. To book a stay on Stayz offering this amenity, enter your preferred travel dates and use the handy filters to select the "air conditioning" box.

How old do you have to be to rent a holiday home in Streeterville?

Age restrictions can differ across properties on Stayz, so look at the rules of the holiday home in Streeterville you're interested in. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Streeterville for?

It really depends on the Streeterville property. To browse a list of options offering extended stays, just type your dates and guest number into Stayz. Enjoy having the place to yourself, along with home comforts like a fully-equipped kitchen and an outdoor space where the kids can run and play. Keep an eye out for long-term stays that offer weekly or monthly discounts.