Streeterville vacation rentals

We found 784 vacation rentals — enter your dates for availability

Discover a selection of 65 homes, 75 apartments, and other vacation rentals in Streeterville that are perfect for your trip. Whether you’re staying in a vacation home with your kids or with friends, you'll have the best amenities for spending time at your home away from home, including WiFi and parking. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Streeterville

Showing deals for:Aug 1 - Aug 8
  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Streeterville

Find out more about Streeterville

Why visit Streeterville

  1. Scenic Chicago Riverwalk: Enjoy a leisurely stroll along the picturesque waterfront, perfect for relaxation and exploration.
  2. Magnificent Mile: Experience premier shopping and dining options in this iconic Chicago destination.
  3. Urban Parks and Beaches: Discover beautiful parks and beaches ideal for family outings and outdoor adventures.
  4. Cultural Experiences: Immerse yourself in the vibrant mix of culture and city life that Streeterville offers.
  5. Diverse Accommodation: Choose from a range of vacation rentals, from cozy studios to luxurious homes, tailored to your needs.

Popular types of accommodation around Streeterville

Discover the ideal vacation rental in Streeterville, Chicago, where you can choose from a variety of accommodations including apart hotels, stylish apartments, and houses. Whether you're seeking a cozy studio apartment or a luxurious getaway, our platform offers transparent information to help you find the perfect streeterville rental that fits your needs. Experience the best of Chicago with the comfort and convenience of your own space.

  • Apartments: The top choice for visitors in Streeterville, offering convenient amenities and a home-like atmosphere for all types of travelers.
  • Houses: A favored option for families and groups seeking spacious, personalized accommodations in the heart of the city.
  • Condos: Popular for their modern features and often spectacular views, ideal for a stylish city getaway.
  • Cottages: A charming retreat that provides a cozy and intimate setting for your stay in Streeterville.
  • Caravan Parks: A unique option for those who enjoy a more outdoorsy experience while still being close to the city's attractions.**

Top attractions around Streeterville

Streeterville, Chicago, is an ideal destination for family vacations and outdoor adventures. With attractions like urban parks, beaches, and modern colleges, it offers a vibrant mix of culture and city experiences. Don't miss the scenic Chicago Riverwalk for a leisurely stroll, making it perfect for travelers seeking both relaxation and exploration in this dynamic neighborhood.

  1. Michigan Avenue: Known as the Magnificent Mile, this bustling street offers vibrant city vibes, lined with upscale shops, restaurants, and iconic architecture. It's a perfect place for shopping and people-watching, just a short stroll from Streeterville.
  2. Navy Pier: A lively jetty featuring stunning waterfront views, art installations, and various entertainment options. Enjoy rides, dining, and friendly atmospheres while taking in the beautiful scenery along the lake.
  3. Millennium Park: This urban oasis is ideal for families and outdoor enthusiasts, featuring lush green spaces, unique art installations, and events throughout the year. It's a perfect spot to relax and enjoy the city vibe.

Things to do recommended for couples

For a romantic getaway in Streeterville, enjoy live music at the House of Blues, just a half-mile away. Indulge in a cozy dinner at the Historic Michael Jordan Restaurant, only 0.2 miles away, and consider a night out at the lively Aragon Ballroom, 6 miles from your stay.

Things to do recommended for families

Families visiting Streeterville can catch a game at Wrigley Field, enjoy the natural beauty at Northerly Island Natural Area, or unwind at The East Bank Club, all offering great experiences for kids and parents alike, ensuring a fun and memorable vacation in Chicago.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a captivating show at the Chicago Theatre, indulge in shopping at the 900 North Michigan Shops, and share laughs at Second City, creating memorable moments filled with culture, entertainment, and family fun.

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

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, as well as features like a full kitchen or outdoor areas for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Streeterville with young kids: Traveling with young kids can be demanding. It's important to prioritize 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 attractions.
  • Taking your pets with you to Streeterville: For many families, a vacation just isn’t the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Many of these pet-friendly homes come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Streeterville: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. 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 around Streeterville

Streeterville offers a vibrant blend of urban life and scenic lake views, making it an ideal destination for families and outdoor enthusiasts. Located in the heart of the city, visitors can explore the renowned Magnificent Mile, filled with shopping and dining options. The friendly atmosphere and romantic spots nearby enhance your experience, ensuring memorable moments whether you’re wandering along the waterfront or enjoying the lively streets.

  • Downtown Chicago: Nestled a mere 0.4 miles from Streeterville, Downtown Chicago is a vibrant hub where urban energy meets family-friendly attractions. This area boasts a bustling shopping scene, with everything from luxury boutiques to popular chain stores. Visitors can catch a game or concert at nearby arenas and indulge in the rich cultural offerings of the city's theaters. Notable landmarks include the iconic Millennium Park, where you can enjoy outdoor art installations and concerts, as well as the renowned United Center, home to the Chicago Bulls and Blackhawks.
  • Magnificent Mile: Just 0.1 miles from Streeterville, Magnificent Mile is a shopper's paradise and a must-visit destination. This lively stretch features high-end retailers, department stores, and unique boutiques, making it perfect for those looking to indulge in a retail therapy session. The area is also home to numerous dining options, ranging from casual eateries to upscale restaurants. Attractions like the historic Water Tower and the Chicago Riverwalk provide scenic backdrops for leisurely strolls, while nearby theaters showcase the best of Chicago's performing arts scene.
  • The Loop: Located 0.8 miles from Streeterville, The Loop is the city's central business district, but it also offers a wealth of attractions for tourists. Here, you can explore a variety of shopping venues and enjoy a vibrant theater scene, with famous venues like the Chicago Theatre. Urban parks, such as Grant Park, offer green spaces for relaxation amidst the city's bustle. The Loop is also home to famous landmarks like the Art Institute of Chicago and the historic Chicago Board of Trade, making it a perfect blend of culture and commerce.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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 CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnyAverageAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageSlightly High
June67.3°F (19.6°C)Light RainMostly SunnySlightly HighSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly LowAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighAverage
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnySlightly LowAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of vacation rental.

Save more with One Key

When you reserve a qualifying Vrbo for your group getaway, you’ll receive OneKeyCash™ on the full booking amount. It really benefits you to take on the role of organizer! Become a part of our One Key rewards program to unlock exclusive savings for members and accumulate OneKeyCash™ on eligible stays. Sign up today and begin earning!

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides a convenient hub for you to plan new adventures, manage your existing plans, and review your bookings. Your saved or booked properties are neatly organized into categories such as Potential, Upcoming, or Current Trips. To check out the Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Streeterville?
According to our data, apartments are the most sought-after property type in Streeterville. But having said that, everyone’s idea of an awesome trip is bound to be different. Vrbo has vacation rentals in a variety of shapes and sizes, and we’ll help you discover the perfect match.
How much does it cost to rent a vacation rental in Streeterville?
Property type, length of stay and time of year are among the factors that can determine the price of a vacation home. Simply click on your travel dates to find your perfect escape. From cozy country cottages to sprawling luxury villas, all Vrbo vacation rentals offer amazing value.
How much does it cost to rent a beach house in Streeterville?
The average price for a vacation rental near the beach in Streeterville will depend on when you’re going and the style and size of property you’re looking for. You can find prices quickly and easily on Vrbo by entering your preferred travel dates. Then use the filter tool to pick the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a hot tub.
Are there pet-friendly vacation rentals in Streeterville?
Yes. You can pick from 79 vacation rentals that allow pets in Streeterville. Several of our pet-friendly vacation rentals come with an outdoor area for your four-legged friend to play around in, complimentary treats, doggie beds and proximity to parks and green space. Apply the “Pets allowed” filter to find your pawfect digs on Vrbo.
Can I rent a house with a pool in Streeterville?
Tick the “pool” box in our handy filter tool and select from 39 houses with private pools in Streeterville on Vrbo. Ball games, gentle soak or noodle joust? How you spend your free time is up to you when your Vrbo vacation home has a swimming pool.
What are popular rental amenities in Streeterville?
When it comes to rental amenities that people are searching for in Streeterville, a garden, a sauna and a firepit rank highest. With Vrbo vacation rentals, there are options to match your taste and style, whether you’re going away with your partner, your family or even pets.
Are there large group vacation rentals in Streeterville?
Streeterville has four vacation homes that can accommodate 10 or more guests. These properties come with the space and privacy you need to share good times with friends and family.
Are there vacation rentals in Streeterville that welcome kids?
Bring the whole group together for a memorable adventure in Streeterville at one of our 79 family-friendly vacation homes. A lot of these stays offer conveniences that are suitable for getaways with the little ones, including laundry facilities, multiple bedrooms and entertainment areas. Just click on the “Properties good for families” filter box and pick your favorite option.
Are there one-bedroom vacation rentals in Streeterville?
Yes, there are 28 one-bedroom properties in Streeterville to select from. A one-bedroom vacation property is a great option if it’s only you and your partner or if you’re flying solo. Toss in more privacy, space and convenience compared to a hotel, and you’re sure to have a memorable trip.
Can I find two-bedroom vacation rentals in Streeterville?
Gather your loved ones and enjoy total privacy and comfort in one of the 22 two-bedroom vacation homes Streeterville has to offer.
Are there vacation rentals with WiFi in Streeterville?
Streeterville has 15 vacation rentals with WiFi, so you’ll be able to stay connected while on vacation. Simply check the “WiFi” box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Vrbo homes make it easy to go online.
How can I find vacation rentals with air conditioning in Streeterville?
Select your dates and then use the filters to view vacation rentals with ac in Streeterville on Vrbo. With 79 air-conditioned properties to choose from here, you can enjoy a cool and comfy break.
How old do you have to be to rent a vacation rental in Streeterville?
The minimum required age is normally 16, 18 or 21. It can differ from property to property on Vrbo, so look at the rules of your preferred Streeterville stay before making a booking.
How long can I rent a vacation rental in Streeterville for?
The amount of time you can book a Streeterville vacation rental for depends on each property. Just enter your travel dates to browse available options offering longer term stays. They have all the things you need to make your extended getaway more comfortable and enjoyable, like kitchens and yards. Some vacation homes may also offer weekly or monthly discounted prices, so you can stick around for longer for less.
Does Vrbo offer discounts for vacation homes in Streeterville?
In Streeterville, you’ll find some incredible deals and discounts for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether you’re off on a mini vacay or a longer stay, we offer plenty of options to suit every kind of traveler.

More Vacation Rentals ideas

People also search for