Best Vacation Homes in Streeterville
10.0
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
10.0
Pet Friendly
Air Conditioner
Internet
Child Friendly
9.4- Fireplace/Heating
Breakfast
Kitchen- Air Conditioner
10.0- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
9.0
Private Pool- Oceanfront
- Fireplace/Heating
Pool
10.0- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
10.0- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
10.0- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
Streeterville Luxury Rentals
9.4- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
- Fireplace/Heating
- Pool
- Kitchen
Parking
- Fireplace/Heating
- Pool
- Kitchen
- Parking
- Fireplace/Heating
- Breakfast
- Kitchen
- Parking
- Fireplace/Heating
- Pool
- Kitchen
- Parking
9.4
Hot Tub- Fireplace/Heating
- Balcony/Terrace
- Kitchen
8.6- Private Pool
Spa- Fireplace/Heating
- Pool
Streeterville Pet Friendly Vacation Rentals
9.8- Oceanfront
- Fireplace/Heating
- Ocean View
View
- Private Pool
- Pool
- Pet Friendly
- Air Conditioner
8.2- Breakfast
- Pet Friendly
- Kitchen
- Parking
9.6- Oceanfront
- Fireplace/Heating
- Ocean View
- View
- Private Pool
- Pool
- Pet Friendly
- Air Conditioner
9.6- Oceanfront
- Fireplace/Heating
- Ocean View
- View
8.0- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
- Spa
- Fireplace/Heating
- Pool
- Pet Friendly
Streeterville Large Vacation Homes
10.0- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
- Child Friendly
- Child Friendly
Why Choose Rent By Owner for your Streeterville Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Streeterville Vacation Rentals
Where are the best neighborhoods to stay in Streeterville?
When choosing a neighborhood to stay in Chicago, Illinois, you’ll find Streeterville offers an ideal combination of vibrant city life and convenient access to iconic attractions. As you explore this lively area, you'll enjoy a well-connected location known for its upscale atmosphere and modern amenities. Whether you're seeking bustling streets or serene waterfront views, Streeterville provides a comfortable and stylish base for your trip. Booking your vacation rentals here ensures you’re close to the city's top attractions, making your visit both enjoyable and effortless.
Downtown Chicago
In the heart of the city, this district offers easy access to iconic attractions and vibrant city life, making it an ideal base for exploring all that the region has to offer. Staying here puts you at the center of convenience and cultural richness.
View 1360+ Rentals in Downtown ChicagoMagnificent Mile
This renowned shopping corridor features upscale boutiques and luxury accommodations, perfect for those seeking a stylish stay within close proximity to key attractions in the area. It's a prime choice for travelers wanting a blend of commerce and entertainment.
View 4124+ Rentals in Magnificent MileRiver North
Known for its vibrant art scene and lively nightlife, this neighborhood offers a dynamic environment just minutes from the city's major cultural venues. It’s an excellent location for visitors wanting energetic surroundings during their stay.
View 351+ Rentals in River NorthNear North Side
Offering a mix of residential comfort and urban excitement, this area provides easy access to popular dining and entertainment options while maintaining a welcoming neighborhood atmosphere. It is well-suited for travelers seeking both convenience and charm.
View 577+ Rentals in Near North SideGold Coast
Famous for its historic architecture and upscale ambiance, the Gold Coast provides a luxurious setting close to top shopping districts and waterfront views. It's an ideal spot for a refined and memorable stay in the region.
View 37+ Rentals in Gold CoastNear East Side
Offering proximity to the lakefront and scenic parks, this neighborhood is perfect for outdoor enthusiasts who want quick access to nature along with city comforts. It provides a peaceful yet accessible environment for your visit.
View 3849+ Rentals in Near East SideRush and Division
With its lively nightlife and trendy dining scene, this area attracts travelers looking to experience the city's vibrant social atmosphere. Staying here means being close to some of the most popular spots for entertainment and cultural exploration.
View 57+ Rentals in Rush and DivisionBest Times to Visit Streeterville
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can greatly enhance your experience, so consider seasonal trends and local events to ensure your stay in this vibrant destination aligns perfectly with your travel plans.
Peak Season Highlights
Summer (June to August)
During the summer months, you can enjoy warm weather and longer daylight hours, perfect for exploring this vibrant city. Expect lively atmosphere and bustling streets in the area.
Fall (September to November)
Autumn offers cooler temperatures and beautiful cityscapes with changing foliage, making it an ideal time for sightseeing and outdoor activities near here.
Off-Season Highlights
Spring (March to May)
In spring, the region experiences mild weather and blooming scenery, providing a pleasant setting for leisurely strolls and exploring the area without the crowds.
Winter (December to February)
Winter brings colder temperatures and occasional snowfall, offering a quieter atmosphere and cozy indoor experiences while still enjoying this destination’s charm.
Weekly Weather Forecast for Streeterville
How to Book Your Streeterville Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Streeterville
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy private outdoor seating areas or balconies with views of the city skyline or lakefront.
- Take advantage of on-site rooftop terraces perfect for relaxing or socializing while overlooking the surrounding neighborhood.
- Make use of shared outdoor swimming pools available in many properties, ideal for unwinding during your stay.
- Benefit from nearby parks and green spaces within walking distance for outdoor activities and picnics.
- Utilize dedicated BBQ grills or outdoor dining spaces to prepare meals while enjoying the fresh air.
- Participate in outdoor fitness areas or walking paths accessible from select rentals, enhancing your active lifestyle here.
- Access waterfront views or proximity to the lakefront, providing scenic outdoor experiences during your visit.
Top Attractions Around Streeterville
What attractions are nearby?
When staying here, you'll find a variety of nearby activities to enjoy in the vibrant region, from exploring cultural attractions to relaxing by the lakeside, all within easy reach of your vacation accommodations.
Family Activities
- Millennium Park:** You can enjoy a family picnic and explore iconic public art installations like the Cloud Gate sculpture in this vibrant urban park.
- Chicago Children's Museum:** Located at Navy Pier, this engaging museum offers hands-on exhibits that inspire creativity and learning for children of all ages.
- Navy Pier Ferris Wheel:** Take a ride on this famous attraction to enjoy stunning views of the city skyline and Lake Michigan with your loved ones.
- Seadog Cruises:** Experience an exciting family-friendly boat tour around the area’s waterways for a memorable adventure on Lake Michigan.
Adult Activities
- Architectural River Cruise: Experience a scenic boat tour along the Chicago River, offering stunning views of the city's iconic skyline and architectural marvels.
- Museum of Contemporary Art Chicago: Explore innovative exhibitions and thought-provoking artworks at this prominent museum nestled in the heart of the city’s vibrant arts district.
- Magnificent Mile Shopping: Indulge in retail therapy on one of the world’s premier shopping corridors, featuring luxury boutiques and renowned department stores.
- Oak Street Beach: Relax or take a leisurely walk along this popular lakeside spot, where you can enjoy panoramic views of Lake Michigan and the city skyline.
Other Places to Stay in Streeterville, IL
Streeterville Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the diverse culinary scene here by trying popular restaurants within walking distance from your vacation rentals, allowing you to experience authentic flavors of the region.
- Visit Iconic Waterfronts: Make time to stroll along the area’s waterfronts to enjoy scenic views and relaxing atmospheres that perfectly complement your stay.
- Utilize Public Transportation: Use the nearby transit options to easily access other parts of the city and discover hidden gems without the hassle of parking or traffic.
- Plan Activities Nearby: Choose accommodations close to key attractions and parks so you can maximize your exploration and make the most of your visit to this vibrant destination.
Transportation Options
- Chicago Transit Authority (CTA) Subway): You can easily access the region's extensive subway system from here, providing quick transportation to many popular Chicago destinations.
- Metra Train Services: The nearby Metra stations connect you to the wider Chicagoland area, offering a convenient option for exploring beyond the city center.
- Public Bus System: The local bus network makes it simple to navigate around this vibrant neighborhood and the surrounding areas without the need for a car.
- Taxi and Rideshare Services: Taxis and rideshare options like Uber and Lyft are readily available, allowing for flexible travel within this dynamic part of the city.
Local Customs Options
- Respect for Local Dining Customs: You’ll find that embracing the neighborhood’s vibrant culinary scene, including its well-known seafood and international cuisine, enhances your experience here.
- Greeting Etiquette: When interacting with residents, a friendly nod or a customary Chicago handshake is appreciated, reflecting the area's warm and welcoming community spirit.
- Queuing Practices: Patience and orderly lines are typical when accessing popular spots or public transportation, ensuring a smooth visit within this bustling city region.
- Celebration of Local Events: Participating in community events and festivals showcases the region's rich cultural traditions and adds an authentic touch to your stay.
Streeterville Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Streeterville?
There are a lot of options in Streeterville. If you plan on staying in the Streeterville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Streeterville:
- Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
- Downtown Guild #3 Mag Mile Gold Coast The Lake!
- Rooms for the Crew | 3 units | Steps to Mag Mile| Navy Pier | 24-hour Gym
- City Center Luxury, Double Queen - The Chicago Hotel Collection Mag Mile
- Shop Chicago and Relax by The Bean | City Viwes | 24-hour Gym | 2 Units
- Lovely Streeterville Studio w/Gym, Pool, near Navy Pier, by Blueground
- Spacious 2 Bed Downtown Chicago with Housekeeping and Laundry. Dogs Welcome.
- Trendy Streeterville Studio w/Pool & Gym, nr Navy Pier, by Blueground
- Streeterville Studio w Gym Pool nr Navy Pier CHI-450
- Chic Corner 2BR in Streeterville | Roof Deck | Lake Views
2. How many vacation rentals have private pools in Streeterville?
There are 9 vacation rentals with private pools near Streeterville. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Streeterville are best for families?
If you are looking for a family-friendly vacation home in Streeterville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Streeterville:
4. How many Rentbyowner vacation rentals are available in Streeterville?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 312 in the Streeterville area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Streeterville.
5. What is the cancellation policy for vacation rentals in Streeterville, Chicago?
6. How do I ensure my booking in this area is secure and reliable?
7. Are there any house rules I should be aware of during my stay?
8. What amenities are usually included in vacation rentals here?
9. What is the check-in and check-out process for vacation rentals in the area?
Streeterville Top Rated Vacation Rentals
9.2- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
9.0- Pool
- Breakfast
- Kitchen
- Parking
9.0- Hot Tub
- Pool
- Breakfast
- Kitchen
8.9- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
8.8- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
8.8- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
8.6- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
