Streeterville holiday homes

We found 682 holiday rentals — enter your dates for availability
Discover a selection of 66 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.
  • 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

Why visit Streeterville

  • Urban Cultural Experience: Dive into Streeterville's rich blend of historic buildings and modern skyscrapers that tell the tale of Chicago's evolution.
  • Artistic Flair: Enjoy local creative expressions at the annual Streeterville Art Fair and engaging local museums.
  • Family-Friendly Vibes: Explore vibrant streets and scenic urban parks that cater to visitors of all ages.
  • Diverse Dining: Relish a variety of culinary delights in a neighbourhood known for its friendly, bustling local culture.
  • Dynamic Cityscape: Immerse yourself in the lively, modern urban charm that makes Streeterville a memorable holiday destination.

Top attractions near Streeterville

Streeterville, Chicago, is a vibrant neighbourhood perfect for family and city-themed holidays. Visitors can explore iconic skyscrapers, lush urban parks, and historic buildings, offering a rich cultural experience. Notable attractions include engaging museums and the annual Streeterville Art Fair, showcasing local talent. With its blend of outdoor activities and urban charm, Streeterville promises memorable experiences for every traveller.

  • Navy Pier: This jettyPier, a mere 2km from Streeterville, offers an urban, scenic escape with friendly locals and lively vibes, perfect for a leisurely stroll.
  • Grant Park: Just 2km from Streeterville, this urban park provides a family-friendly, outdoor urban retreat, ideal for enjoying the city's charm.
  • 875 North Michigan Avenue: A skyscraper located 644m from Streeterville, showcasing distinct city vibes and a modern architectural highlight.

Things to do recommended for couples

Seeking a romantic getaway in Streeterville? Enjoy a scenic walk along the waterfront at Navy Pier or indulge in a sunset boat cruise on Lake Michigan. Don't miss a candlelit dinner at a rooftop restaurant with stunning skyline views for an unforgettable evening together.

Things to do recommended for families

Families visiting Streeterville can explore the Shedd Aquarium, home to fascinating marine life, and enjoy interactive exhibits at the Chicago Children's Museum. Don't miss a stroll along the waterfront at Navy Pier, where rides and games await the kids for a memorable day out.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a scenic stroll along the waterfront at Navy Pier, indulge in local cuisine at vibrant eateries, and take a thrilling architectural boat tour through the Chicago River to admire the city's iconic skyline.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Streeterville

Whether you’re travelling with a group, as a family, with your furry mates, or seeking a longer stay, be sure to filter using the appropriate priorities. Here are some Vrbo booking tips for you.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all of these options and more on Vrbo.
  • Traveling to Streeterville with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Streeterville: For many, a family holiday isn’t truly fulfilling without their furry companion along for the adventure. If this resonates with you, explore the Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Streeterville: If you’re after holiday rentals that offer month-long or extended stay deals, you’ve come to the right spot. Use the appropriate filters to effortlessly discover and save on long-term rentals. You might also want to include extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Streeterville

Experience the vibrant urban life in Streeterville, Chicago, where family-friendly attractions meet scenic city views. Wander the bustling streets, indulge in diverse dining, and enjoy outdoor spaces perfect for city explorations. Discover the charm of Streeterville neighbourhoods, where each corner offers a blend of modern business vibes and friendly local culture. This unique slice of Chicago promises a memorable holiday experience for every traveller.

  • Chicago, Downtown Chicago, Magnificent Mile: Chicago, the vibrant city encompassing Streeterville, offers a rich blend of family-friendly, outdoor, and urban experiences. Visitors can enjoy a variety of shopping areas, arena entertainment facilities, and theatres. The city is home to notable landmarks such as a sports facility stadium, a bustling tourist precinct, and an expansive urban park, making it a destination that caters to diverse interests.
  • Downtown Chicago: Located 644m from Streeterville, Downtown Chicago is a dynamic neighbourhood renowned for its lively urban atmosphere. It invites families, outdoor enthusiasts, and city explorers to immerse themselves in a setting filled with shopping areas, arena entertainment facilities, and theatres. Attractions such as a tourist precinct, a sports facility stadium, and an urban park are in close proximity, providing plenty of options for a well-rounded day out.
  • Magnificent Mile: Just 161m from Streeterville, the Magnificent Mile is celebrated for its iconic city vibe and family-friendly attractions. This neighbourhood offers a delightful mix of shopping areas, educational venues, and arena entertainment facilities. Visitors can easily access local highlights like a tourist precinct, a sports facility stadium, and an urban park, ensuring a memorable and varied travel experience.

Best time to go to Streeterville

If you're planning a trip to Streeterville, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverage
March37.0°F (2.8°C)Light RainMostly CloudyAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly High
August73.0°F (22.8°C)Light RainMostly SunnySlightly Low
September67.1°F (19.5°C)Light RainMostly SunnySlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly Low
December33.1°F (0.6°C)Light RainMostly CloudyAverage

Booking with Vrbo is a breeze

Looking to save on your upcoming holiday? Consider keeping your travel dates flexible since prices can fluctuate. Plus, opting for a longer stay might offer you even better savings. To find the ideal Vrbo property that fits your budget, simply use our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a helpful space for you to create new trips, carry on with your plans, or review and manage your bookings. The properties you’ve saved or booked are conveniently sorted into Potential, Upcoming, or Current Trips. To check out the Trip Boards, head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

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, Bookabach 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 Bookabach 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 Bookabach 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 Bookabach. 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 Bookabach, 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 Bookabach 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, Bookabach'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 Bookabach 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 Bookabach 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 Bookabach, 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 Bookabach. 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.