Streeterville holiday lettings

We found 672 holiday rentals — enter your dates for availability
Discover a selection of 62 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.

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Why visit Streeterville

  • Scenic waterfront: Enjoy breathtaking views along Lake Michigan, perfect for leisurely strolls and outdoor activities.
  • Cultural attractions: Discover engaging museums and historic buildings that showcase the rich heritage of the area.
  • Streeterville Art Fair: Experience the vibrant local art scene at this annual event, featuring talented artists and unique artworks.
  • Diverse dining options: Indulge in a variety of eateries offering everything from casual bites to fine dining experiences.
  • Family-friendly activities: Engage in numerous outdoor adventures suitable for all ages, making it a perfect family destination.

Popular types of accommodation around Streeterville

Streeterville, a vibrant neighbourhood in Chicago, Illinois, offers a captivating blend of urban excitement and scenic beauty. Visitors can explore iconic landmarks, enjoy waterfront views, and indulge in diverse dining options. The area features a variety of vacation rentals, including stylish apartments, private homes, and modern condos. Whether you're seeking a studio apartment or a spacious family retreat, Streeterville promises an unforgettable experience in the heart of the Windy City.

  • Apartments: These are the most sought-after lodging options in Streeterville, offering modern amenities and convenient locations for your stay.
  • Houses: A fantastic choice for those seeking a more personal and spacious environment, these homes provide privacy and comfort.
  • Condos: Ideal for short-term stays, condos combine hotel-like services with the comforts of home, perfect for exploring the area.
  • Villas: These luxurious options offer ample space and upscale features, making them perfect for families or groups.
  • Cottages: Charming and quaint, cottages provide a cosy escape with a homey feel, perfect for relaxation.**

Top attractions near Streeterville

Streeterville, Chicago, is a vibrant neighbourhood perfect for family outings and outdoor adventures. Visitors can admire stunning skyscrapers, explore urban parks, and discover historic buildings. Highlights include engaging museums and cultural attractions, making it an ideal spot for family experiences and city-themed holidays. The annual Streeterville Art Fair adds a unique local flavour, showcasing artistic talent amidst the urban landscape. Streeterville truly offers a delightful blend of culture and city life for all travellers.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with high-end shops, restaurants, and iconic architecture, offering a vibrant urban atmosphere perfect for leisurely strolls and shopping.
  • Navy Pier: A popular destination with stunning views of Lake Michigan, Navy Pier features attractions like rides, gardens, and dining options, creating a friendly and scenic environment for all visitors.
  • Millennium Park: This urban oasis is home to impressive art installations, beautiful gardens, and outdoor concerts, making it a perfect spot for families and those seeking a relaxing outdoor experience.

Things to do recommended for couples

Seeking a romantic escape in Streeterville? Enjoy a leisurely walk along the picturesque Lakefront Trail, or indulge in a sunset boat cruise on the Chicago River. Don’t forget to explore the charming cafés and intimate restaurants that offer delightful dining experiences for couples.

Things to do recommended for families

Families will delight in the interactive exhibits at the Chicago Children's Museum, explore the wonders of the Shedd Aquarium, or enjoy a leisurely stroll along the scenic Lakefront Trail. Don't miss the iconic Navy Pier for rides and entertainment suitable for all ages.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a scenic stroll along the Chicago Riverwalk, take an architectural boat tour to admire the city’s skyline, and indulge in a group dining experience at the renowned Navy Pier, where entertainment and local cuisine await.

*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

If you're planning a trip with friends, family, pets, or seeking extended stays, it's essential to filter your options based on your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all of these options, and many more, on Vrbo.
  • Traveling to Streeterville with young kids: Travelling with young children can present its challenges. It’s important to prioritise their comfort and safety, as well as access to suitable amenities like a private swimming pool. Additionally, considering your closeness to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Streeterville: For many, a family holiday isn’t truly complete without their furry companion by their side. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Streeterville: If you’re seeking holiday rentals that offer discounts for stays of a month or more, you’ve come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include additional features in your search, such as a parking space, a well-equipped kitchen, or a private pool.

Where to stay near Streeterville

Streeterville, a vibrant neighbourhood in Chicago, offers an exciting blend of urban charm and scenic views. Visitors can explore the stunning waterfront along Lake Michigan, marvel at iconic landmarks, and enjoy family-friendly activities in the area. With its friendly atmosphere and plethora of dining options, Streeterville provides an ideal setting for outdoor adventures and urban exploration, making it a perfect destination for travellers seeking an unforgettable experience in the heart of the Windy City.

  • Chicago: As a vibrant metropolis, Chicago is a treasure trove of experiences for travellers seeking family-friendly activities, outdoor adventures, and urban exploration. Nestled in the heart of the Windy City, Streeterville offers easy access to iconic attractions such as the Millennium Park, where you can enjoy outdoor concerts and art installations. Additionally, the nearby sports facilities and theatres provide a dynamic entertainment landscape, making it an ideal base for your Chicago visit.
  • Downtown Chicago: Located a mere 644m from Streeterville, Downtown Chicago is the bustling core of the city, brimming with life and excitement. This area is renowned for its spectacular shopping venues, theatres, and vibrant dining options, catering to all tastes. Attractions like the Chicago Riverwalk invite leisurely strolls, while sports facilities nearby offer thrilling game-day experiences. Whether you’re exploring the famous architecture or indulging in local cuisine, Downtown Chicago promises an unforgettable urban adventure.
  • Magnificent Mile: Just 161m from Streeterville, the Magnificent Mile is a shopper's paradise, featuring an array of world-class shops and boutiques. This lively neighbourhood combines culture and leisure, with educational attractions and entertainment venues, including theatres and concert halls. Stroll along the picturesque streets lined with stunning architecture, and take in the vibrant atmosphere. The Magnificent Mile is also home to beautiful urban parks, making it a perfect spot for families to relax and enjoy the scenery.

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 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 a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a dedicated area for you to plan new trips, manage your existing arrangements, or review your bookings. The properties you’ve saved or reserved are conveniently categorised into Potential, Upcoming, or Current Trips. To discover more about Trip Boards, please 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 in Streeterville?
In Streeterville, apartments are the predominant type of holiday rental, with several available throughout the area. These apartments are typically situated in vibrant locations, close to popular attractions such as Navy Pier and the Museum of Contemporary Art. Guests can expect modern amenities, including fully equipped kitchens, spacious living areas, and often stunning views of Lake Michigan. The urban setting offers a lively option, making these rentals an ideal base for exploring the local dining and entertainment options.
Are there any beach house rentals in Streeterville?
In Streeterville, there are several beach house rentals available, offering a great experience in this vibrant neighbourhood of Chicago. These rentals typically feature spacious layouts, with amenities such as fully equipped kitchens, modern furnishings, and comfortable living areas. Many properties also include outdoor spaces where guests can enjoy views of Lake Michigan, making them superb for relaxation after a day of exploring nearby attractions like Navy Pier and the Museum of Contemporary Art.
How much does it cost to rent a holiday home in Streeterville?
Prices for holiday rentals in Streeterville vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Streeterville to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Streeterville holiday house rentals?
You can find great discounts on house rentals in Streeterville on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What are popular rental amenities in Streeterville?
In Streeterville, popular rental amenities include a selection of properties that feature a nearby beach and access to a casino, making it an appealing destination for both relaxation and entertainment. Most holiday rentals come equipped with essential conveniences such as a coffee and tea maker, ensuring guests can enjoy warm beverages at their leisure. Many units also offer a deck or patio, providing outdoor space to unwind and take in the cityscape. Additionally, a desk is often available in the accommodations, suiting those who may need to work or study during their stay.*You must be at least 18 years old to participate in gambling activities in the United Kingdom. Please gamble responsibly. If you feel that gambling is affecting your life, seek help from organisations such as BeGambleAware at www.begambleaware.org or call their helpline at 0808 8020 133.
Can I find family house rentals in Streeterville?
In Streeterville, Illinois, there are several family-friendly house rentals available, making it a great choice for those travelling with children. This vibrant neighbourhood is conveniently located near Lake Michigan and offers a mix of spacious homes that cater to families. Many properties feature ample living spaces, full kitchens for preparing family meals, and comfortable bedrooms to ensure a restful stay.Visitors can enjoy proximity to top attractions such as the Navy Pier, where there are amusement rides and family-friendly entertainment options, as well as the Shedd Aquarium, which is great for a fun and educational outing. Additionally, the area is filled with parks and green spaces, providing opportunities for outdoor activities and relaxation.
Are there any Streeterville holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Streeterville with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I book pet-friendly holiday rentals in Streeterville?
In Streeterville, there are several pet-friendly holiday rentals available, making it a great choice for travellers who wish to bring their furry companions along. This vibrant neighbourhood is known for its stunning waterfront views and proximity to attractions like Navy Pier and the picturesque Lake Michigan shoreline. Many of the holiday rentals here offer modern amenities such as fully equipped kitchens, spacious living areas, and access to fitness centres or rooftop terraces, providing a comfortable stay for both humans and pets.In addition to the inviting accommodations, Streeterville is situated near several parks, including the scenic Ohio Street Beach and the expansive Grant Park, where pets can enjoy leisurely walks and outdoor activities. The area's pet-friendly cafes and shops also enhance the experience, allowing visitors to explore the local scene alongside their pets.
Can I find long-stay holiday rentals in Streeterville?
A long-stay holiday rental in Streeterville is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Streeterville for a holiday rental?
September is the most popular time to visit Streeterville, offering a delightful blend of warm weather and vibrant city life. The peak season runs from July to September, with tourists flocking to the area to take advantage of the bustling atmosphere, festivals, and outdoor activities. Visitors can enjoy scenic strolls along Lake Michigan, explore the nearby Millennium Park, and experience the city's renowned dining scene—all while basking in pleasant temperatures typically ranging from 15 to 25 degrees Celsius.As summer transitions into autumn, September provides a comfortable climate for outdoor adventures and sightseeing. The city's waterfront parks are great for leisurely walks or picnics, and the bustling streets come alive with events, making it an ideal time for socialising and exploring.For those looking to save a bit on accommodation, November presents an excellent opportunity. This quieter month allows for a more relaxed exploration of Streeterville's attractions, including indoor activities such as visiting museums and enjoying the local coffee shops without the summer crowds.
Are there any remote work holiday rentals in Streeterville?
In Streeterville, Illinois, there are several holiday rentals that cater to remote work needs. This vibrant neighbourhood, situated by Lake Michigan, offers a range of accommodations equipped with essential amenities for those working from home. Many properties include dedicated office spaces or desks, high-speed internet access, and comfortable living areas that can serve as productive work environments.In addition to the practical features for remote work, Streeterville boasts a lively option with nearby attractions such as Navy Pier and the Museum of Contemporary Art. After work hours, guests can enjoy scenic walks along the lakefront or explore the diverse dining options in the area. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Streeterville holiday rental?
Book your Streeterville holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price. *Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Streeterville, Illinois, United States of America?
In Streeterville, visitors can enjoy a variety of attractions that highlight the area's vibrant culture and scenic views. One of the main draws is Navy Pier, a bustling hub featuring entertainment, dining, and stunning views of Lake Michigan. The pier is also home to the Chicago Children's Museum and the iconic Ferris wheel, making it a great spot for families.Just a short walk away, the Museum of Contemporary Art offers engaging exhibitions and a lovely café, while the historic Water Tower and the nearby Chicago Avenue Pumping Station provide a glimpse into the city's architectural history. For those interested in shopping, the area boasts high-end retail options along Michigan Avenue, often referred to as the Magnificent Mile.Additionally, the picturesque Ohio Street Beach is nearby, offering a serene escape where visitors can relax by the water.
Can I change or cancel my Streeterville home rental booking on Vrbo?
To find Streeterville holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Streeterville holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way. Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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