Streeterville holiday lettings

We found 830 holiday rentals — enter your dates for availability

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:14 Nov - 21 Nov
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Find out more about Streeterville

Find out more about Streeterville

Why visit Streeterville

  • Striking architecture: Marvel at the impressive skyscrapers and historic buildings that define Streeterville's skyline.
  • Cultural attractions: Discover a range of museums and cultural sites that enrich the visitor experience.
  • Beautiful urban parks: Enjoy the scenic beauty and recreational opportunities in the area's lush green spaces.
  • Walkable neighbourhood: Experience the vibrant streets of downtown Chicago, perfect for leisurely exploration.
  • Diverse accommodation: Choose from stylish apartments, modern condos, and inviting vacation homes for a comfortable stay.

Popular types of accommodation around Streeterville

If you're contemplating a getaway to Streeterville, you're in for a treat. Our most sought-after accommodation options include stylish apartments, inviting houses, and modern condos. Whether you’re looking for Streeterville apartments or a chic Chicago Streeterville apartment, we have a variety of choices to suit your needs. Discover the perfect base for your adventure with our selection of apartments in Streeterville.

  • Apartments: The top choice for visitors in Streeterville, offering convenient stays with amenities for a comfortable experience.
  • Houses: A popular option for families or groups seeking the comforts of home during their holiday.
  • Condos: Ideal for those wanting a blend of hotel-like services and home-like comfort in a vibrant setting.
  • Cottages: A charming alternative for those looking for a quaint and peaceful retreat.
  • Villas: Spacious and luxurious, perfect for travellers wanting an upscale getaway.**

Top attractions near Streeterville

Streeterville is an ideal destination for families and those seeking a vibrant city experience. Visitors can explore striking skyscrapers, beautiful urban parks, and historic buildings. The area offers a rich cultural experience with attractions like the illustrious Streeterville and various museums, ensuring there's something for everyone. Whether you're looking for outdoor adventures or family-friendly activities, Streeterville has a delightful mix of attractions to enjoy during your stay.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is a vibrant hub of shopping, dining, and entertainment, offering a true taste of city life.
  • Navy Pier: A scenic jetty featuring parks, gardens, and attractions, Navy Pier is perfect for leisurely strolls, enjoying urban views, and experiencing a friendly atmosphere.
  • Millennium Park: This expansive urban park is ideal for families, featuring art installations, lush outdoor spaces, and a lively city vibe, making it a perfect spot for relaxation and recreation.

Things to do recommended for couples

For a romantic getaway in Streeterville, indulge in live music at the House of Blues, just half 1.6km away, or enjoy a lovely meal at the Historic Michael Jordan Restaurant, a mere 124m from your stay. Don't miss the vibrant atmosphere and unforgettable experiences!

Things to do recommended for families

Families can immerse themselves in the excitement of Wrigley Field, explore the serene Northerly Island Natural Area, or unwind at The East Bank Club, all within a short distance from Streeterville, offering a delightful mix of sports and relaxation for everyone.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a captivating performance at the Chicago Theatre, indulge in laughter at Second City, or shop at Chicago Place Mall, all within easy reach. Each venue offers a unique atmosphere, perfect for creating memorable experiences together.

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

If you’re planning a trip with a group, family, or pets, or if you’re seeking longer stays, be sure to utilise the appropriate filters to suit your needs. Here are some helpful booking tips for Vrbo.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, as well as additional features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Streeterville with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, as well as access to suitable amenities, like a private swimming pool. Additionally, you might want to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Streeterville: For many families, a holiday wouldn’t be the same without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Streeterville: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and benefit from monthly rental savings. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Streeterville

Streeterville offers a delightful blend of urban charm and scenic beauty, making it an ideal destination for families and outdoor enthusiasts. Explore the vibrant streets of downtown Chicago, where friendly locals and captivating architecture await. The neighbourhood is not only walkable but also features some of the city's best attractions, ensuring a memorable holiday experience. Nearby areas promise a mix of business and leisure, providing a perfect backdrop for your Chicago adventure.

  • Chicago: Chicago, a vibrant metropolis located 559m from Streeterville, offers a dynamic mix of urban experiences. Visitors flock to this city for its family-friendly attractions, outdoor activities, and rich cultural scene. Explore the city's shopping areas, enjoy thrilling events at the arena entertainment facilities, or delve into the educational offerings at various institutions. Notable landmarks include iconic stadiums and sports facilities that contribute to the city's exciting atmosphere. With diverse neighbourhoods and a bustling downtown, Chicago is a must-visit for an unforgettable urban adventure.
  • Downtown Chicago: Just 249m from Streeterville, Downtown Chicago is the heart of the city, bustling with activity and excitement. This neighbourhood is perfect for families seeking a blend of outdoor adventures and city-themed experiences. Enjoy the vibrant shopping areas, catch a show at a local theatre, or attend events at the arena entertainment facilities. Key landmarks include prominent tourist precincts and stadiums that showcase the city's sporting spirit. With its stunning skyline and endless entertainment options, Downtown Chicago is an essential stop for any traveller.
  • Magnificent Mile: Nestled a mere 62m from Streeterville, the Magnificent Mile is a premier shopping district that attracts visitors from all over. Known for its family-friendly atmosphere and outdoor experiences, this lively area features an array of shopping venues, entertainment options, and educational attractions. The iconic tourist precinct and nearby stadiums highlight the neighbourhood's vibrant character. Stroll along the bustling streets, indulge in world-class shopping, or enjoy a delightful meal at one of the many restaurants, all while soaking in the charm of this iconic Chicago destination.

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. Peak season runs in June to July and September, while off-peak times, like January, August and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudyAverageSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageSlightly Low
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighSlightly High
August73.0°F (22.8°C)Light RainMostly SunnySlightly LowSlightly High
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageAverage
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageAverage

Booking with Vrbo is simple

Looking to cut costs on your next holiday? Consider being flexible with your travel dates, as prices can fluctuate quite a bit. Moreover, extending your stay can often result in significant savings. To discover the ideal Vrbo accommodation that suits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy platform for you to plan new trips, easily resume your previous ones, and manage your travel arrangements. You can view the properties you've saved or booked, neatly organised into categories like Potential, Upcoming, or Current Trips. To begin exploring Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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.

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