Streeterville vacation rentals

We found 700 vacation rentals — enter your dates for availability

Discover a selection of 79 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 skyline of Chicago, featuring architectural masterpieces that define the city.
  • Lake Michigan Views: Enjoy breathtaking views and recreational activities along the picturesque shores of Lake Michigan.
  • Diverse Dining: Savor a wide range of culinary delights in the many restaurants, from casual eateries to upscale dining.
  • Urban Parks: Relax and unwind in beautiful urban parks that offer green spaces amidst the bustling city.
  • Luxury Accommodations: Experience a stay in stylish apartments, condos, or renowned hotels for a memorable trip.

Popular types of accommodation around Streeterville

If you're exploring vacation rentals in Streeterville, you're in for a treat. Our most popular accommodations include stylish apartments, cozy houses, and modern condos. For those seeking luxury, consider the renowned star hotels or the Peninsula Hotel. If you prefer a more intimate setting, check out our studio apartments or upscale luxury options, including southwest Chicago apartments. Whatever your preference, we have the perfect place for your stay in this vibrant neighborhood.

  • Apartments: The top choice for vacation rentals in Streeterville, offering a range of amenities and convenient locations.
  • Houses: A popular option for those seeking a home-like atmosphere with privacy for families or groups.
  • Condos: Ideal for travelers looking for modern living spaces with shared facilities and a vibrant community feel.
  • Cottages: Quaint and cozy, these rentals provide a charming retreat for a peaceful getaway.
  • Villas: Luxurious and spacious accommodations perfect for travelers wanting a taste of upscale living.**

Top attractions near Streeterville

Streeterville offers a delightful blend of family-friendly activities and urban adventures, making it perfect for city-themed vacations. Visitors can explore iconic skyscrapers, relax in urban parks, and admire historic buildings. With a variety of cultural experiences, Streeterville caters to travelers seeking exploration and enjoyment in this vibrant part of Chicago.

  • Michigan Avenue: Known as the Magnificent Mile, this vibrant street is packed with shopping, dining, and cultural experiences, making it a bustling hub of city life just 0.2 miles from Streeterville.
  • Navy Pier: This iconic pier, located 1 mile away, offers stunning waterfront views, entertainment options, and friendly people, perfect for a leisurely day out.
  • Millennium Park: Just 0.7 miles from Streeterville, this urban park features beautiful gardens, public art, and family-friendly activities, making it an ideal outdoor escape in the heart of the city.

Things to do recommended for couples

For a romantic getaway in Streeterville, enjoy live music at the House of Blues, just 0.5 miles away. Savor a delightful meal at the Historic Michael Jordan Restaurant, only 0.2 miles from your stay. Cap off your evening with a concert at the Aragon Ballroom, 6 miles away.

Things to do recommended for families

Families will love visiting Wrigley Field, just 4 miles away, to soak up the sports atmosphere. For a tranquil experience, Northerly Island Natural Area, 3 miles away, offers wellness vibes, while The East Bank Club, only 0.9 miles distant, provides great recreational activities for all ages.

Things to do recommended for groups

Your group can enjoy a show at the historic Chicago Theatre, just 0.6 miles away, experience laughter at Second City, 1 mile away, or indulge in shopping at Chicago Place Mall, only 0.2 miles away, all while soaking in the vibrant local culture and atmosphere of Streeterville.

*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 traveling with a group, family, pets, or planning an extended stay, it's important to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Streeterville with a group: Think about how many bedrooms you'll require, along with additional features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily refine your search for all these options and more on Vrbo.
  • Traveling to Streeterville with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with ensuring access to age-appropriate facilities, 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 trip isn't truly complete without their beloved pets. If that resonates with you, take a look at Vrbo listings that welcome furry companions. Most pet-friendly accommodations come equipped with feeding bowls and 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 offering discounts for stays of a month or more, you've come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding features like a parking space, a well-equipped kitchen, or a private pool to your search criteria as well.

Where to stay near Streeterville

Streeterville, a vibrant neighborhood in downtown Chicago, offers an ideal blend of urban excitement and scenic beauty for families and outdoor enthusiasts alike. Visitors can explore stunning views of Lake Michigan, dine at diverse restaurants, and enjoy friendly locals. Just a short walk away, the bustling atmosphere of nearby neighborhoods enhances the experience, making it a perfect base for discovering the charm of Chicago's rich culture and stunning skyline.

  • Chicago: As a vibrant metropolis, Chicago is the heart of the Midwest, and Streeterville is nestled within its bustling landscape. Visitors flock to Chicago for an array of family-friendly activities, outdoor adventures, and urban exploration. The city boasts a rich tapestry of attractions, including world-class shopping areas, sports facilities, and educational venues. Noteworthy landmarks close to Streeterville include iconic stadiums and a lively tourist precinct, all contributing to the city’s energetic atmosphere.
  • Downtown Chicago: Located a mere 0.4 miles from Streeterville, Downtown Chicago is a dynamic neighborhood that captures the essence of city life. Known for its family-friendly attractions and outdoor experiences, this area is a hub for entertainment, with numerous shopping venues, theaters, and arena facilities. Notable highlights include its proximity to tourist precincts and sports stadiums, making Downtown Chicago a must-visit for anyone seeking to immerse themselves in the city’s vibrant culture.
  • Magnificent Mile: Just 0.1 miles from Streeterville, the Magnificent Mile is an iconic stretch known for its upscale shopping, dining, and entertainment options. This neighborhood attracts families and city enthusiasts alike, offering a blend of outdoor experiences and cultural attractions. Visitors can explore a plethora of shopping areas, indulge in various educational experiences, and enjoy entertainment at nearby arena facilities. With its proximity to essential landmarks like stadiums and tourist precincts, the Magnificent Mile is a highlight of any Chicago itinerary.

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

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can really help, as prices tend to vary. Additionally, booking a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort 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 total booking amount. Being the organizer certainly has its perks. Enroll in our One Key rewards program to unlock exclusive member discounts and accumulate OneKeyCash on eligible stays. Sign up today and start reaping the benefits.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers an easy-to-use area where you can plan new trips, continue from where you last stopped, or review and arrange your travel plans. Here, you’ll see your saved or booked properties organized into categories like Potential, Upcoming, and Current Trips. To begin utilizing Trip Boards, simply head over to: 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, vacation houses are a popular rental choice, with about 10 available in the area. These properties typically feature spacious living areas, fully equipped kitchens, and outdoor spaces, making them ideal for families or groups looking for more room during their stay. Additionally, there are several apartments scattered throughout the neighborhood, offering a more compact stay with amenities such as modern furnishings, kitchen facilities, and access to building amenities like gyms or rooftop terraces.
Are there any beach house rentals in Streeterville?
In Streeterville, Illinois, there are several beach house rentals available, primarily offering a luxurious experience near the picturesque shores of Lake Michigan. These rentals typically feature modern amenities such as fully equipped kitchens, spacious living areas, and outdoor spaces like balconies or terraces that provide stunning views of the lake and city skyline. Streeterville is known for its vibrant atmosphere, with attractions like Navy Pier and the Chicago Riverwalk nearby, making these rentals superb for travelers looking to enjoy both relaxation and urban exploration.
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 fitness facilities, which cater to travelers looking to maintain their workout routines. Many rentals are conveniently located near museums, providing easy access for those interested in exploring cultural attractions. Furthermore, some properties permit pets, accommodating travelers who wish to bring their furry companions. Onsite parking is also a common feature, making it convenient for guests with vehicles.
Are there any family house rentals in Streeterville?
In Streeterville, Illinois, there are numerous family-friendly house rentals available, with about 11 options to choose from. This vibrant neighborhood, located along the picturesque shores of Lake Michigan, offers a fantastic urban experience for families. Many of the properties feature spacious living rooms, fully equipped kitchens, and dining areas superb for family meals. Guests can also enjoy amenities such as outdoor terraces, fitness centers, and even access to communal pools.

Close to top attractions like Navy Pier, the Museum of Contemporary Art, and the scenic Lakeshore Park, families will find plenty of entertainment and recreational activities nearby. The area is well-connected by public transportation, making it easy to explore the broader Chicago cityscape.
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.
Are there pet-friendly vacation rentals in Streeterville?
In Streeterville, there are several pet-friendly vacation rentals available, with a total of 12 options to choose from. This vibrant neighborhood offers modern accommodations that often come equipped with amenities such as full kitchens, in-unit laundry, and fitness centers, providing travelers with a comfortable stay. Many properties feature spacious living areas and access to rooftop decks, where guests can enjoy views of the city.

Streeterville is conveniently located near several parks, making it an excellent choice for pet owners. The nearby Ohio Street Beach offers a scenic area for walks, while the expansive Grant Park is just a short distance away, featuring walking trails and green spaces. Additionally, the neighborhood is home to pet-friendly cafes and shops, creating an inviting space for those traveling with pets.
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.
Are there any remote work vacation rentals in Streeterville?
In Streeterville, Illinois, there are several remote work vacation rentals available, with around 12 options to choose from. This vibrant neighborhood, located along the shores of Lake Michigan, offers a unique blend of urban amenities and scenic views. Travelers can expect rentals equipped with essential remote work amenities such as high-speed Wi-Fi, desks, and dedicated office spaces, making it convenient for those who need to balance work and leisure.

The area is also known for its proximity to points of interest like Navy Pier, where visitors can enjoy entertainment, shops, and dining options. Additionally, the nearby Magnificent Mile offers a wealth of shopping and cultural experiences. Many of the vacation rentals in Streeterville feature modern furnishings, fully equipped kitchens, and access to fitness centers or rooftop lounges, providing a comfortable and productive environment for remote workers. 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?
In Streeterville, visitors can enjoy numerous attractions that highlight the neighborhood's vibrant urban landscape and waterfront access. The renowned Navy Pier is a major draw, offering entertainment options such as rides, dining, and stunning views of Lake Michigan. Nearby, the Museum of Contemporary Art showcases an impressive collection of modern works and hosts various exhibitions throughout the year.

For those interested in shopping and dining, the Magnificent Mile, which runs just south of Streeterville, features a mix of high-end retailers and popular restaurants. The area is also close to the iconic John Hancock Center, where visitors can ascend to the observation deck for panoramic views of the city.
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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