Navy Pier which includes wild flowers and general coastal views as well as a couple

Streeterville holiday lettings

We found 816 holiday rentals — enter your dates for availability

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Dates

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Flexible dates

June 2025

July 2025

Discover a selection of 66 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:5 Sept - 12 Sept

Huge, well designed condo that provides plenty of space and comfort!

Exceptional

(14 reviews)

River North 3BR/2BA: HUGE, Parking, Center Chicago

Chicago, IL

7% off

£833 per night

includes taxes & fees

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

Exceptional

(33 reviews)

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

Chicago, Illinois

7% off

£436 per night

includes taxes & fees

Exceptional

(39 reviews)

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

Chicago, Illinois

7% off

£459 per night

includes taxes & fees

Exceptional

(27 reviews)

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

Chicago, Illinois

7% off

£446 per night

includes taxes & fees

Exceptional

(26 reviews)

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

Chicago, Illinois

7% off

£477 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

Kasa Magnificent Mile Chicago

Sleeps 3 · 1 bedroom

Top rated rentals - Streeterville

Premier Host

Best Apartment I’m Chicago

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, 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 rental accommodation in Streeterville?

Apartments are the most popular style of holiday rental in Streeterville, according to our data. Even if you’ve got something else in mind, Vrbo 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 rental 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 Vrbo holiday rentals 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 Vrbo 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 rentals in Streeterville?

Pack a tug toy and treats for the pup in your life because Streeterville has 73 holiday rentals 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 rentals on Vrbo. 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 Vrbo, and then spend your days splishing and splashing in a swimming pool that’s for your use only.

What are popular rental amenities in Streeterville?

When it comes to rental amenities that people look for in Streeterville, a garden, a nearby waterfront and nearby museums rank highest. With Vrbo holiday rentals, 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 rentals 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 rentals 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 rentals in Streeterville?

Take your pick from 23 one-bedroom rentals in Streeterville. Whether you’re looking for a cosy chalet or a fancy condo, Vrbo’s one-bedroom rentals 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 rentals 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 rentals with WiFi in Streeterville?

Streeterville has 12 holiday rentals 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 Vrbo homes will keep you online.

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

Streeterville has 73 holiday rentals where you can relax and recharge in air-conditioned comfort. To book a stay on Vrbo 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 rental in Streeterville?

Age restrictions can differ across properties on Vrbo, 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 rental 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 Vrbo. 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.