Streeterville holiday homes

We found 673 holiday rentals — enter your dates for availability
Discover a selection of 60 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 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.
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.
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.
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 Bookabach.
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.
Are all fees included in the Streeterville holiday homes prices shown on Bookabach?
Bookabach 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.
Are there any Streeterville holiday homes with parking?
Bookabach offers a wide selection of holiday homes 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 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.
Are there any discounts for Streeterville holiday homes?
You can find great discounts on holiday homes in Streeterville on Bookabach, 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.
Can I change or cancel my Streeterville holiday home booking on Bookabach?
To find Streeterville holiday rentals with free cancellation, just use Bookabach'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". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Streeterville?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach'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 favourites, and build the perfect itinerary together.
How early should I book a Streeterville holiday home?
Book your Streeterville holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Streeterville?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Streeterville to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach 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.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, 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.
Why should I join Bookabach as a host?
Joining Bookabach 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, Bookabach 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 Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas