Streeterville vacation rentals

We found 716 vacation rentals — enter your dates for availability

Discover a selection of 77 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.

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Find out more about Streeterville

Why visit Streeterville

  • Iconic Skyscrapers: Marvel at the stunning architecture of Chicago's famous skyscrapers, offering breathtaking views of the city skyline.
  • Urban Parks: Relax in beautiful urban parks, perfect for picnics, strolls, and family gatherings amidst nature.
  • Cultural Experiences: Immerse yourself in the diverse cultural offerings, including museums, galleries, and local events.
  • Walkable Streets: Enjoy the friendly atmosphere and vibrant streets, ideal for leisurely walks and exploring local shops.
  • Variety of Accommodations: Choose from stylish apartments and cozy vacation homes for a comfortable stay in the heart of the city.

Popular types of accommodation around Streeterville

Planning a getaway to Streeterville? You'll find a variety of vacation rentals to suit your needs, including stylish apartments, cozy houses, and modern condos. Whether you're searching for streeterville apartments, spacious bedroom apartments, or a convenient studio apartment, there's something for everyone. Explore the vibrant neighborhood of Streeterville, Chicago, and enjoy a stay that offers both comfort and convenience.

  • Apartments: The top choice for visitors to Streeterville, offering modern amenities and convenience for a comfortable stay.
  • Houses: A popular option for those seeking more space and a home-like atmosphere, perfect for families and groups.
  • Condos: A favored choice featuring stylish living spaces, often located in vibrant areas close to attractions.
  • Cottages: A quaint and cozy option for travelers looking for charm and a peaceful ambiance.
  • Villas: An upscale accommodation choice, ideal for those desiring luxury and privacy during their visit.**

Top attractions near Streeterville

Streeterville, Chicago, offers a vibrant mix of family-friendly and outdoor activities, ideal for city-themed vacations. Visitors can explore iconic skyscrapers, relax in urban parks, and stroll through lively streets. The area is rich in cultural experiences, making it a perfect destination for families and travelers seeking a blend of urban excitement and leisure. Don't miss out on the local attractions that showcase the charm and energy of this dynamic neighborhood.

  • Michigan Avenue: Known as the Magnificent Mile, this bustling street is lined with upscale shops, restaurants, and iconic architecture, offering a vibrant urban experience just 0.2 miles from Streeterville.
  • Navy Pier: A lively waterfront destination 1 mile away, Navy Pier features stunning views of Lake Michigan, entertainment options, and a friendly atmosphere, making it perfect for families and tourists alike.
  • Millennium Park: Located 0.7 miles from Streeterville, this urban park boasts beautiful gardens, public art installations, and outdoor spaces ideal for families seeking relaxation and city vibes.

Things to do recommended for couples

Discover romance in Streeterville, Chicago. Enjoy a sunset walk along the Lakefront Trail, take a scenic boat tour on the Chicago River, and savor a candlelit dinner at a rooftop restaurant with stunning skyline views. Don’t miss a couples' spa day for ultimate relaxation.

Things to do recommended for families

Families will love exploring the interactive exhibits at the Chicago Children's Museum, just a short walk away. Enjoy a leisurely stroll along the Navy Pier, where you can ride the Ferris wheel and savor delicious snacks. Don't miss the beautiful lakeside parks for outdoor fun.

Things to do recommended for groups

Groups visiting Streeterville can enjoy a scenic stroll along the waterfront at Navy Pier, take a thrilling architecture boat tour on the Chicago River, and explore the interactive exhibits at the Museum of Contemporary Art for a memorable local experience.

*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

When planning your trip, whether with a group, family, or pets, or if you're considering longer stays, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, along with features like a full kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Streeterville with young kids: Traveling with young kids can present its own set of challenges. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities, like a private swimming pool. Additionally, being close to family-friendly attractions can enhance your experience.
  • Taking your pets with you to Streeterville: For many families, a vacation isn’t truly fulfilling without their furry companions. If you relate to this, explore Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and cozy beds, ensuring that every member of your family feels comfortable and at home.
  • Planning for a long term stay visiting Streeterville: If you're in search of vacation 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 features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Streeterville

Streeterville, a vibrant neighborhood in Chicago, offers a delightful mix of urban charm and scenic beauty, perfect for families and outdoor enthusiasts. Explore the stunning city views, walkable streets, and friendly atmosphere while enjoying nearby attractions in downtown Chicago. This desirable area promises an unforgettable vacation experience filled with family-friendly activities and a warm urban vibe, making it an ideal base for your adventures in the Windy City.

  • Chicago: As a vibrant metropolis, Chicago offers an array of experiences that cater to families, outdoor enthusiasts, and city explorers alike. Nestled along the shores of Lake Michigan, this iconic city is renowned for its stunning architecture and cultural landmarks. Visitors can enjoy a variety of attractions, including the famous Millennium Park, where the Cloud Gate sculpture (also known as The Bean ) captivates all. Sports fans will appreciate the energetic atmosphere surrounding Wrigley Field and United Center, while shopping enthusiasts can explore the diverse retail options throughout the city.
  • Downtown Chicago: Located just 0.4 miles from Streeterville, Downtown Chicago is the bustling core of the city, known for its impressive skyline and rich cultural offerings. Families can take advantage of the many outdoor spaces, including Grant Park, while shoppers will delight in the variety of stores lining State Street. The area is also home to world-class theaters and arenas, making it a prime destination for entertainment. With nearby landmarks such as the Art Institute of Chicago and the Chicago Riverwalk, Downtown Chicago promises a memorable experience for all visitors.
  • Magnificent Mile: Situated a mere 0.1 miles from Streeterville, the Magnificent Mile is a premier shopping and dining district that showcases the best of Chicago. This vibrant neighborhood is perfect for families and city explorers seeking a blend of excitement and relaxation. Here, you'll find a plethora of high-end shops, dining options, and iconic attractions like the historic Water Tower and the Museum of Contemporary Art. The Magnificent Mile also offers easy access to beautiful urban parks, making it a great spot for outdoor enjoyment amidst the urban landscape.

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 a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate significantly. Plus, opting for a longer stay can often result in substantial savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Planning made easy

Vrbo's Trip Board feature offers you a convenient way to plan your travel. You can easily create new trips, pick up from where you last left off, or view and organize your travel plans. All the properties you've saved or booked are now organized into categories like Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Streeterville?
In Streeterville, apartments are the most popular type of vacation rental, with several options available throughout this vibrant neighborhood. Many of these apartments are situated near popular attractions such as Navy Pier and the Magnificent Mile, providing easy access to a variety of dining, shopping, and entertainment experiences. Travelers can expect modern amenities in these rentals, including fully equipped kitchens, spacious living areas, and often stunning views of Lake Michigan or the city skyline.
Are there any beach house rentals in Streeterville?
In Streeterville, there are several beach house rentals available, predominantly found near the picturesque shoreline of Lake Michigan. These properties are typically well-equipped, offering amenities such as fully stocked kitchens, spacious living areas, and outdoor balconies or patios that provide stunning views of the lake and city skyline. Many rentals also include access to communal facilities like swimming pools and fitness centers, making them ideal for both relaxation and recreation.
How much does it cost to rent a vacation home in Streeterville?
Prices for vacation 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 vacation 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 convenient features like a coffee and tea maker, which appeals to travelers wanting a cozy start to their mornings. Many rentals also offer a deck or patio, providing outdoor space to relax and enjoy the vibrant city atmosphere. For those needing to work remotely or stay organized, a desk is commonly available in these accommodations. Additionally, the proximity to nearby attractions such as beaches and casinos enhances the appeal of these rentals, allowing guests to easily explore the lively entertainment options available in the area.

*Please play responsibly. You must be at least 21 years old to participate in any form of gambling in the United States. If you believe you have a gambling problem, seek help from professional organizations such as the National Council on Problem Gambling at www.ncpgambling.org or call their helpline at 1-800-522-4700.
Can I find family house rentals in Streeterville?
In Streeterville, a vibrant neighborhood in Chicago, there are several family-friendly house rentals available. Visitors can expect spacious rooms that often feature multiple bedrooms, allowing families to enjoy comfortable sleeping arrangements. Many of these homes come with well-equipped kitchens, making it easy to prepare meals together after a day of exploring the city.

Streeterville is not far from popular attractions such as Navy Pier, where families can enjoy rides, games, and a stunning view of the skyline. Additionally, the nearby Museum of Contemporary Art and the scenic Lakeshore Park offer opportunities for outdoor activities and cultural experiences. With amenities like Wi-Fi, air conditioning, and laundry facilities, these rentals provide a convenient base for families looking to experience the best of Chicago.
Are there any Streeterville vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Streeterville with parking available—perfect for families or travelers 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 vacation rentals in Streeterville?
In Streeterville, travelers will find several pet-friendly vacation rentals that cater to both comfort and convenience. This vibrant neighborhood, located along the shores of Lake Michigan, offers a mix of modern apartments and stylish condos, many of which come equipped with amenities such as fully stocked kitchens, fitness centers, and rooftop terraces with stunning views of the city skyline and the lake.

The nearby Ohio Street Beach provides a lovely outdoor space where pets can enjoy the fresh air, and the expansive Grant Park is just a short distance away, offering plenty of green space for walks and relaxation. Additionally, the area is home to pet-friendly cafes and shops, ideal for those traveling with furry companions.
Can I find long-stay vacation rentals in Streeterville?
A long-stay vacation rental in Streeterville is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* 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.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
When is the best time to visit Streeterville for a vacation rental?
September is the most popular time to visit Streeterville, as it offers a great blend of pleasant weather and vibrant activities. The peak season, stretching from July through September, attracts travelers looking to enjoy the beautiful lakeshore and the bustling city atmosphere. During this time, you can enjoy outdoor adventures, such as exploring Navy Pier, relaxing in nearby parks, or taking scenic walks along Lake Michigan.

In September, temperatures typically range from the mid-50s to the low 70s Fahrenheit, creating a comfortable environment for sightseeing and enjoying the local festivals. This month features the Chicago Gourmet food festival, which is a highlight for food enthusiasts eager to experience the city's culinary scene.

For those seeking a more budget-friendly option, November presents a wonderful opportunity to explore the city without the summer crowds. You can enjoy the city's rich culture and history at a more leisurely pace, visiting museums and attractions that are less crowded, allowing for a more intimate experience.
Are there any remote work vacation rentals in Streeterville?
In Streeterville, Illinois, travelers seeking remote work vacation rentals will find several options available. This vibrant neighborhood, known for its proximity to Lake Michigan and iconic attractions like Navy Pier and the Art Institute of Chicago, offers a variety of accommodations tailored for remote workers. Many of these rentals come equipped with essential amenities such as high-speed internet, dedicated desk spaces, and comfortable work environments, making it easy to stay productive while enjoying the city's offerings.

Streeterville's bustling atmosphere also ensures that you'll have access to numerous cafes and restaurants, great for a change of scenery during work breaks. Additionally, the area's scenic waterfront and parks provide great opportunities for relaxation after a day of remote work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Streeterville vacation rental?
Book your Streeterville vacation 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 vacation 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 mix of cultural and recreational attractions. The iconic Navy Pier, a bustling entertainment hub, offers rides, restaurants, and stunning views of Lake Michigan. Nearby, the Chicago Shakespeare Theater hosts excellent performances, making it a cultural highlight in the area.

For art enthusiasts, the Museum of Contemporary Art is located within walking distance, featuring innovative exhibitions and programs. The scenic Lakeshore Drive also provides beautiful waterfront views, great for leisurely walks or bike rides along the lakefront.

Additionally, the area is home to luxurious shopping options at the nearby Magnificent Mile, where visitors can explore high-end boutiques and dining establishments.
Can I change or cancel my Streeterville home rental booking on Vrbo?
To find Streeterville vacation 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 rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, 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 travelers 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 cozy cabin or a beach condo, 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 vacation 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 like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, 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 organizing 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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